{"product_id":"siprhcl-cas-258278-25-0","title":"SIPr·HCl | CAS 258278-25-0 | ≥95%","description":"\u003cdiv style=\"margin-bottom: 28px;\"\u003e\n\u003cdiv style=\"background: #002147; padding: 10px 20px; margin-bottom: 0;\"\u003e\u003ch3 style=\"margin: 0; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; font-size: 0.70em; font-weight: bold; letter-spacing: 0.12em; text-transform: uppercase; color: #fff;\"\u003eTechnical Specifications\u003c\/h3\u003e\u003c\/div\u003e\n\u003ctable style=\"width: 100%; border-collapse: collapse; font-size: 0.95em; border: 1px solid #e4e8f0; border-top: none; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif;\"\u003e\u003ctbody\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eCAS Number\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e258278-25-0\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eEC \/ EINECS Number\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e627-991-8\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eMDL Number\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003eMFCD07369796\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eSMILES\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0; word-break: break-all;\"\u003eCC(C)C1=C(C(=CC=C1)C(C)C)N2CC[N+](=C2)C3=C(C=CC=C3C(C)C)C(C)C.[Cl-]\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eInChI\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0; word-break: break-all;\"\u003eInChI=1S\/C27H39N2.ClH\/c1-18(2)22-11-9-12-23(19(3)4)26(22)28-15-16-29(17-28)27-24(20(5)6)13-10-14-25(27)21(7)8;\/h9-14,17-21H,15-16H2,1-8H3;1H\/q+1;\/p-1\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eInChIKey\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0; word-break: break-all;\"\u003eLWPXTYZKAWSRIP-UHFFFAOYSA-M\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003ePubChem CID\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e2734918\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eMolecular Formula\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003eC₂₇H₃₉ClN₂\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eMolecular Weight\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e427.1 g\/mol\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eMelting Point\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e289–293 °C (lit.)\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eSolubility\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003eSoluble in methanol.\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003ePurity\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e≥95%\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003ePhysical Form\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003eWhite to off-white crystalline powder\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eHS Code\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003e2933.29\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; border-bottom: 1px solid #e4e8f0; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eShelf Life\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333; border-bottom: 1px solid #e4e8f0;\"\u003eRetest period: 36 months from date of manufacture\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003ctr\u003e\n\u003ctd style=\"padding: 9px 16px; font-weight: 600; color: #002147; width: 200px; background: #f7f8fb; font-size: 0.95em; vertical-align: top;\"\u003eStorage Conditions\u003c\/td\u003e\n\u003ctd style=\"padding: 9px 16px; color: #333;\"\u003eStore in a cool, dry place in a tightly sealed container, protected from light.\u003c\/td\u003e\n\u003c\/tr\u003e\n\u003c\/tbody\u003e\u003c\/table\u003e\n\u003c\/div\u003e\n\u003cdiv style=\"margin-bottom: 28px;\"\u003e\n\u003cdiv style=\"background: #002147; padding: 10px 20px; margin-bottom: 0;\"\u003e\u003ch3 style=\"margin: 0; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; font-size: 0.70em; font-weight: bold; letter-spacing: 0.12em; text-transform: uppercase; color: #fff;\"\u003eProduct Description \u0026amp; Scientific Applications\u003c\/h3\u003e\u003c\/div\u003e\n\u003cdiv style=\"padding: 16px 20px; border: 1px solid #e4e8f0; border-top: none; font-family: Georgia, 'Times New Roman', serif; font-size: 0.95em; line-height: 1.65; color: #333;\"\u003e\u003cdiv\u003e\n\u003cp\u003e\u003cstrong\u003eSIPr·HCl\u003c\/strong\u003e (1,3-bis(2,6-diisopropylphenyl)imidazolinium chloride) is a precursor to the free N-heterocyclic carbene (NHC) 1,3-bis(2,6-diisopropylphenyl)-2-imidazolidinylidene (SIPr). SIPr is a saturated NHC ligand. The salt is also used to form catalysts in situ for a variety of reactions, for example amination, Heck coupling, ring-opening metathesis polymerisation (ROMP) and hydrogenation. It has been used in a one-pot synthesis of N-heterocyclic carbene–allylpalladium complexes.\u003c\/p\u003e\n\u003cdiv style=\"margin:8px 0 18px 0;\"\u003e\n\u003cdiv style=\"display:flex;flex-wrap:wrap;align-items:center;justify-content:flex-start;gap:2px;\"\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\n\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"141px\" height=\"168px\" viewbox=\"0 0 141 168\"\u003e\u003cpath d=\"M 129.2,95.9 L 110.0,97.6\"\u003e\u003c\/path\u003e\u003cpath d=\"M 110.0,97.6 L 99.0,82.0\"\u003e\u003c\/path\u003e\u003cpath d=\"M 110.0,97.6 L 102.0,115.0\"\u003e\u003c\/path\u003e\u003cpath d=\"M 102.0,115.0 L 113.4,130.7\"\u003e\u003c\/path\u003e\u003cpath d=\"M 113.4,130.7 L 105.5,148.4\"\u003e\u003c\/path\u003e\u003cpath d=\"M 110.0,131.0 L 103.5,145.7\"\u003e\u003c\/path\u003e\u003cpath d=\"M 105.5,148.4 L 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44.9,23.1\"\u003e\u003c\/path\u003e\u003cpath d=\"M 44.9,23.1 L 44.9,42.5\"\u003e\u003c\/path\u003e\u003cpath d=\"M 47.8,24.8 L 47.8,40.8\"\u003e\u003c\/path\u003e\u003cpath d=\"M 44.9,42.5 L 28.1,52.2\"\u003e\u003c\/path\u003e\u003cpath d=\"M 28.1,52.2 L 11.3,42.5\"\u003e\u003c\/path\u003e\u003cpath d=\"M 28.1,52.2 L 28.1,71.5\"\u003e\u003c\/path\u003e\u003cpath d=\"M 65.9,74.6 L 77.3,82.9\"\u003e\u003c\/path\u003e\u003cpath d=\"M 82.7,117.0 L 102.0,115.0\"\u003e\u003c\/path\u003e\u003cpath d=\"M 84.7,119.7 L 100.6,118.1\"\u003e\u003c\/path\u003e\u003cpath d=\"M 77.3,82.9 L 72.7,97.1\"\u003e\u003c\/path\u003e\u003cpath d=\"M 44.9,42.5 L 61.7,52.2\"\u003e\u003c\/path\u003e\u003cpath d=\"M 112.8,129.9 L 113.4,130.7 L 113.0,131.6\"\u003e\u003c\/path\u003e\u003cpath d=\"M 105.9,147.5 L 105.5,148.4 L 104.5,148.5\"\u003e\u003c\/path\u003e\u003cpath d=\"M 87.2,150.3 L 86.2,150.4 L 85.6,149.6\"\u003e\u003c\/path\u003e\u003cpath d=\"M 52.7,101.3 L 52.0,101.3 L 51.7,100.4\"\u003e\u003c\/path\u003e\u003cpath d=\"M 46.3,83.9 L 46.0,82.9 L 46.5,82.5\"\u003e\u003c\/path\u003e\u003cpath d=\"M 78.4,24.1 L 78.4,23.1 L 77.6,22.6\"\u003e\u003c\/path\u003e\u003cpath d=\"M 62.5,13.9 L 61.7,13.4 L 60.8,13.9\"\u003e\u003c\/path\u003e\u003cpath d=\"M 45.7,22.6 L 44.9,23.1 L 44.9,24.1\"\u003e\u003c\/path\u003e\u003cpath d=\"M 76.7,82.5 L 77.3,82.9 L 77.1,83.7\"\u003e\u003c\/path\u003e\u003ctext x=\"67.7\" y=\"107.4\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eN\u003c\/text\u003e\u003ctext x=\"58.1\" y=\"77.5\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eN\u003c\/text\u003e\u003ccircle cx=\"80.9\" cy=\"84.1\" r=\"0.6\" fill=\"#000\" stroke=\"none\"\u003e\u003c\/circle\u003e\u003ccircle cx=\"80.9\" cy=\"81.7\" r=\"0.6\" fill=\"#000\" stroke=\"none\"\u003e\u003c\/circle\u003e\u003c\/svg\u003e\n\u003c\/div\u003e\n\u003c\/div\u003e\n\u003cp style=\"font-size:12px;margin:4px 0 0 0;\"\u003e\u003cem\u003eGeneral reaction: SIPr·HCl + base → SIPr (free carbene).\u003c\/em\u003e\u003c\/p\u003e\n\u003c\/div\u003e\n\u003cp\u003e\u003cstrong\u003eN-Arylation of indoles.\u003c\/strong\u003e In a study of palladium\/imidazolium salt systems for amination reactions, less reactive indoles were converted to N-aryl indoles with SIPr·HCl as the supporting ligand. The palladium(II) acetate\/SIPr·HCl\/sodium hydroxide system was efficient for the N-arylation of diverse indoles with aryl bromides.\u003c\/p\u003e\n\u003cdiv style=\"margin:8px 0 18px 0;\"\u003e\n\u003cdiv style=\"display:flex;flex-wrap:wrap;align-items:center;justify-content:flex-start;gap:2px;\"\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\n\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"75px\" height=\"59px\" viewbox=\"0 0 75 59\"\u003e\u003cpath d=\"M 68.9,44.0 L 68.9,24.8\"\u003e\u003c\/path\u003e\u003cpath d=\"M 66.0,42.4 L 66.0,26.5\"\u003e\u003c\/path\u003e\u003cpath d=\"M 68.9,24.8 L 52.3,15.2\"\u003e\u003c\/path\u003e\u003cpath d=\"M 52.3,15.2 L 35.6,24.9\"\u003e\u003c\/path\u003e\u003cpath d=\"M 52.3,18.6 L 38.5,26.5\"\u003e\u003c\/path\u003e\u003cpath d=\"M 35.6,24.9 L 21.6,20.3\"\u003e\u003c\/path\u003e\u003cpath d=\"M 13.1,24.8 L 6.1,34.5\"\u003e\u003c\/path\u003e\u003cpath d=\"M 6.1,34.5 L 17.4,50.0\"\u003e\u003c\/path\u003e\u003cpath d=\"M 9.6,34.5 L 18.5,46.6\"\u003e\u003c\/path\u003e\u003cpath d=\"M 17.4,50.0 L 35.6,44.1\"\u003e\u003c\/path\u003e\u003cpath d=\"M 35.6,44.1 L 52.3,53.7\"\u003e\u003c\/path\u003e\u003cpath d=\"M 38.5,42.4 L 52.3,50.3\"\u003e\u003c\/path\u003e\u003cpath d=\"M 52.3,53.7 L 68.9,44.0\"\u003e\u003c\/path\u003e\u003cpath d=\"M 35.6,44.1 L 35.6,24.9\"\u003e\u003c\/path\u003e\u003cpath d=\"M 68.9,43.1 L 68.9,44.0 L 68.1,44.5\"\u003e\u003c\/path\u003e\u003cpath d=\"M 68.9,25.8 L 68.9,24.8 L 68.1,24.4\"\u003e\u003c\/path\u003e\u003cpath d=\"M 53.1,15.7 L 52.3,15.2 L 51.4,15.7\"\u003e\u003c\/path\u003e\u003cpath d=\"M 6.4,34.0 L 6.1,34.5 L 6.6,35.3\"\u003e\u003c\/path\u003e\u003cpath d=\"M 16.8,49.2 L 17.4,50.0 L 18.3,49.7\"\u003e\u003c\/path\u003e\u003cpath d=\"M 51.5,53.2 L 52.3,53.7 L 53.1,53.2\"\u003e\u003c\/path\u003e\u003ctext x=\"13.8\" y=\"24.9\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eN\u003c\/text\u003e\u003ctext x=\"13.8\" y=\"14.4\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eH\u003c\/text\u003e\u003c\/svg\u003e\n\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003cdiv style=\"font-size:20px;padding:0 4px;align-self:center;\"\u003e+\u003c\/div\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\n\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"45px\" height=\"11px\" viewbox=\"0 0 45 11\"\u003e\u003cpath d=\"M 16.6,4.2 L 27.6,4.2\"\u003e\u003c\/path\u003e\u003ctext x=\"4.1\" y=\"10.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eA\u003c\/text\u003e\u003ctext x=\"12.4\" y=\"10.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003er\u003c\/text\u003e\u003ctext x=\"28.2\" y=\"10.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eB\u003c\/text\u003e\u003ctext x=\"36.5\" y=\"10.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003er\u003c\/text\u003e\u003c\/svg\u003e\n\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003cdiv style=\"display:flex;flex-direction:column;align-items:center;justify-content:center;min-width:90px;max-width:150px;padding:0 4px;text-align:center;font-size:12px;line-height:1.3;\"\u003e\n\u003cdiv\u003ePd(OAc)₂\u003c\/div\u003e\n\u003cdiv style=\"font-size:30px;line-height:1;\"\u003e⟶\u003c\/div\u003e\n\u003cdiv\u003eSIPr·HCl, NaOH\u003c\/div\u003e\n\u003c\/div\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\n\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"79px\" height=\"68px\" viewbox=\"0 0 79 68\"\u003e\u003cpath d=\"M 61.9,15.8 L 59.5,23.2\"\u003e\u003c\/path\u003e\u003cpath d=\"M 62.3,33.3 L 69.4,43.1\"\u003e\u003c\/path\u003e\u003cpath d=\"M 69.4,43.1 L 58.1,58.7\"\u003e\u003c\/path\u003e\u003cpath d=\"M 65.8,43.1 L 57.0,55.3\"\u003e\u003c\/path\u003e\u003cpath d=\"M 58.1,58.7 L 39.7,52.7\"\u003e\u003c\/path\u003e\u003cpath d=\"M 39.7,52.7 L 23.0,62.3\"\u003e\u003c\/path\u003e\u003cpath d=\"M 36.8,51.0 L 23.0,59.0\"\u003e\u003c\/path\u003e\u003cpath d=\"M 23.0,62.3 L 6.3,52.7\"\u003e\u003c\/path\u003e\u003cpath d=\"M 6.3,52.7 L 6.3,33.4\"\u003e\u003c\/path\u003e\u003cpath d=\"M 9.2,51.0 L 9.2,35.1\"\u003e\u003c\/path\u003e\u003cpath d=\"M 6.3,33.4 L 23.0,23.8\"\u003e\u003c\/path\u003e\u003cpath d=\"M 23.0,23.8 L 39.7,33.4\"\u003e\u003c\/path\u003e\u003cpath d=\"M 23.0,27.1 L 36.8,35.1\"\u003e\u003c\/path\u003e\u003cpath d=\"M 39.7,33.4 L 53.8,28.8\"\u003e\u003c\/path\u003e\u003cpath d=\"M 39.7,33.4 L 39.7,52.7\"\u003e\u003c\/path\u003e\u003cpath d=\"M 69.1,42.6 L 69.4,43.1 L 68.8,43.9\"\u003e\u003c\/path\u003e\u003cpath d=\"M 58.6,57.9 L 58.1,58.7 L 57.1,58.4\"\u003e\u003c\/path\u003e\u003cpath d=\"M 23.8,61.9 L 23.0,62.3 L 22.2,61.9\"\u003e\u003c\/path\u003e\u003cpath d=\"M 7.1,53.2 L 6.3,52.7 L 6.3,51.7\"\u003e\u003c\/path\u003e\u003cpath d=\"M 6.3,34.4 L 6.3,33.4 L 7.2,32.9\"\u003e\u003c\/path\u003e\u003cpath d=\"M 22.2,24.2 L 23.0,23.8 L 23.9,24.2\"\u003e\u003c\/path\u003e\u003ctext x=\"60.5\" y=\"15.1\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eA\u003c\/text\u003e\u003ctext x=\"68.7\" y=\"15.1\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003er\u003c\/text\u003e\u003ctext x=\"54.5\" y=\"33.5\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eN\u003c\/text\u003e\u003c\/svg\u003e\n\u003c\/div\u003e\n\u003c\/div\u003e\n\u003cp style=\"font-size:12px;margin:4px 0 0 0;\"\u003e\u003cem\u003eGeneral reaction: indole + Ar–Br → N-aryl indole; Ar = aryl.\u003c\/em\u003e\u003c\/p\u003e\n\u003c\/div\u003e\n\u003cp\u003e\u003cstrong\u003eSuzuki–Miyaura coupling with aryldiazonium salts.\u003c\/strong\u003e In one study, SIPr·HCl with palladium(II) acetate, without added base, was used as the catalyst to cross-couple aryl, vinyl and alkyl boronic acids and boronates with aryldiazonium tetrafluoroborates. Diazonium ions formed in situ also took part in the coupling.\u003c\/p\u003e\n\u003cdiv style=\"margin:8px 0 18px 0;\"\u003e\n\u003cdiv style=\"display:flex;flex-wrap:wrap;align-items:center;justify-content:flex-start;gap:2px;\"\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\n\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"56px\" height=\"34px\" viewbox=\"0 0 56 34\"\u003e\u003cpath d=\"M 17.4,23.4 L 27.0,17.9\"\u003e\u003c\/path\u003e\u003cpath d=\"M 38.5,11.4 L 43.2,8.7\"\u003e\u003c\/path\u003e\u003cpath d=\"M 37.1,8.9 L 41.8,6.2\"\u003e\u003c\/path\u003e\u003cpath d=\"M 39.9,13.8 L 44.6,11.1\"\u003e\u003c\/path\u003e\u003ctext x=\"4.9\" y=\"30.8\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eA\u003c\/text\u003e\u003ctext x=\"13.2\" y=\"30.8\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003er\u003c\/text\u003e\u003ctext x=\"27.6\" y=\"21.5\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eN\u003c\/text\u003e\u003ctext x=\"35.9\" y=\"16.7\" style=\"font-size:7px;font-style:normal;font-weight:normal;fill-opacity:1;stroke:none;font-family:sans-serif;text-anchor:start;fill:#000000\"\u003e+\u003c\/text\u003e\u003ctext x=\"43.8\" y=\"12.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eN\u003c\/text\u003e\u003c\/svg\u003e\n\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003cdiv style=\"font:12px sans-serif;padding:0 2px 0 0;margin-left:-2px;\"\u003eBF₄⁻\u003c\/div\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003cdiv style=\"font-size:20px;padding:0 4px;align-self:center;\"\u003e+\u003c\/div\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\n\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"58px\" height=\"46px\" viewbox=\"0 0 58 46\"\u003e\u003cpath d=\"M 12.6,33.2 L 20.6,28.6\"\u003e\u003c\/path\u003e\u003cpath d=\"M 24.8,22.0 L 24.8,13.9\"\u003e\u003c\/path\u003e\u003cpath d=\"M 29.0,28.6 L 36.9,33.2\"\u003e\u003c\/path\u003e\u003ctext x=\"4.8\" y=\"41.6\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eR\u003c\/text\u003e\u003ctext x=\"21.2\" y=\"32.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eB\u003c\/text\u003e\u003ctext x=\"21.3\" y=\"13.3\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eO\u003c\/text\u003e\u003ctext x=\"29.5\" y=\"13.3\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eH\u003c\/text\u003e\u003ctext x=\"37.5\" y=\"41.7\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eO\u003c\/text\u003e\u003ctext x=\"45.8\" y=\"41.7\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eH\u003c\/text\u003e\u003c\/svg\u003e\n\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003cdiv style=\"display:flex;flex-direction:column;align-items:center;justify-content:center;min-width:90px;max-width:150px;padding:0 4px;text-align:center;font-size:12px;line-height:1.3;\"\u003e\n\u003cdiv\u003ePd(OAc)₂, SIPr·HCl\u003c\/div\u003e\n\u003cdiv style=\"font-size:30px;line-height:1;\"\u003e⟶\u003c\/div\u003e\n\u003cdiv\u003eno added base\u003c\/div\u003e\n\u003c\/div\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\n\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"40px\" height=\"11px\" viewbox=\"0 0 40 11\"\u003e\u003cpath d=\"M 16.5,4.2 L 27.5,4.2\"\u003e\u003c\/path\u003e\u003ctext x=\"4.1\" y=\"10.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eA\u003c\/text\u003e\u003ctext x=\"12.4\" y=\"10.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003er\u003c\/text\u003e\u003ctext x=\"28.1\" y=\"10.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eR\u003c\/text\u003e\u003c\/svg\u003e\n\u003c\/div\u003e\n\u003c\/div\u003e\n\u003cp style=\"font-size:12px;margin:4px 0 0 0;\"\u003e\u003cem\u003eGeneral reaction: Ar–N₂⁺ BF₄⁻ + R–B(OH)₂ → Ar–R; R = aryl, vinyl or alkyl; boronates also react.\u003c\/em\u003e\u003c\/p\u003e\n\u003c\/div\u003e\n\u003cp\u003e\u003cstrong\u003eMizoroki–Heck coupling with aryldiazonium salts.\u003c\/strong\u003e In a related study, the same combination of SIPr·HCl and palladium(II) acetate, without added base, gave Heck coupling products from olefins and aryldiazonium tetrafluoroborates. Diazonium ions formed in situ directly from anilines also coupled.\u003c\/p\u003e\n\u003cdiv style=\"margin:8px 0 18px 0;\"\u003e\n\u003cdiv style=\"display:flex;flex-wrap:wrap;align-items:center;justify-content:flex-start;gap:2px;\"\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\n\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"56px\" height=\"34px\" viewbox=\"0 0 56 34\"\u003e\u003cpath d=\"M 17.4,23.4 L 27.0,17.9\"\u003e\u003c\/path\u003e\u003cpath d=\"M 38.5,11.4 L 43.2,8.7\"\u003e\u003c\/path\u003e\u003cpath d=\"M 37.1,8.9 L 41.8,6.2\"\u003e\u003c\/path\u003e\u003cpath d=\"M 39.9,13.8 L 44.6,11.1\"\u003e\u003c\/path\u003e\u003ctext x=\"4.9\" y=\"30.8\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eA\u003c\/text\u003e\u003ctext x=\"13.2\" y=\"30.8\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003er\u003c\/text\u003e\u003ctext x=\"27.6\" y=\"21.5\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eN\u003c\/text\u003e\u003ctext x=\"35.9\" y=\"16.7\" style=\"font-size:7px;font-style:normal;font-weight:normal;fill-opacity:1;stroke:none;font-family:sans-serif;text-anchor:start;fill:#000000\"\u003e+\u003c\/text\u003e\u003ctext x=\"43.8\" y=\"12.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eN\u003c\/text\u003e\u003c\/svg\u003e\n\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003cdiv style=\"font:12px sans-serif;padding:0 2px 0 0;margin-left:-2px;\"\u003eBF₄⁻\u003c\/div\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003cdiv style=\"font-size:20px;padding:0 4px;align-self:center;\"\u003e+\u003c\/div\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\n\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"24px\" height=\"42px\" viewbox=\"0 0 24 42\"\u003e\u003cpath d=\"M 21.9,3.7 L 21.9,22.6\"\u003e\u003c\/path\u003e\u003cpath d=\"M 19.1,3.7 L 19.1,21.0\"\u003e\u003c\/path\u003e\u003cpath d=\"M 21.9,22.6 L 9.7,29.6\"\u003e\u003c\/path\u003e\u003cpath d=\"M 21.9,21.6 L 21.9,22.6 L 21.3,22.9\"\u003e\u003c\/path\u003e\u003ctext x=\"1.9\" y=\"38.1\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eR\u003c\/text\u003e\u003c\/svg\u003e\n\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003cdiv style=\"display:flex;flex-direction:column;align-items:center;justify-content:center;min-width:90px;max-width:150px;padding:0 4px;text-align:center;font-size:12px;line-height:1.3;\"\u003e\n\u003cdiv\u003ePd(OAc)₂, SIPr·HCl\u003c\/div\u003e\n\u003cdiv style=\"font-size:30px;line-height:1;\"\u003e⟶\u003c\/div\u003e\n\u003cdiv\u003eno added base\u003c\/div\u003e\n\u003c\/div\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\n\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"75px\" height=\"23px\" viewbox=\"0 0 75 23\"\u003e\u003cpath d=\"M 55.2,7.9 L 43.2,14.8\"\u003e\u003c\/path\u003e\u003cpath d=\"M 43.2,14.8 L 27.1,5.5\"\u003e\u003c\/path\u003e\u003cpath d=\"M 43.2,11.6 L 28.5,3.1\"\u003e\u003c\/path\u003e\u003cpath d=\"M 27.1,5.5 L 15.2,12.4\"\u003e\u003c\/path\u003e\u003cpath d=\"M 43.8,14.5 L 43.2,14.8 L 42.4,14.3\"\u003e\u003c\/path\u003e\u003cpath d=\"M 27.9,5.9 L 27.1,5.5 L 26.5,5.8\"\u003e\u003c\/path\u003e\u003ctext x=\"55.8\" y=\"11.5\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eA\u003c\/text\u003e\u003ctext x=\"64.1\" y=\"11.5\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003er\u003c\/text\u003e\u003ctext x=\"7.4\" y=\"20.8\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eR\u003c\/text\u003e\u003c\/svg\u003e\n\u003c\/div\u003e\n\u003c\/div\u003e\n\u003cp style=\"font-size:12px;margin:4px 0 0 0;\"\u003e\u003cem\u003eGeneral reaction: Ar–N₂⁺ BF₄⁻ + olefin → Heck coupling product.\u003c\/em\u003e\u003c\/p\u003e\n\u003c\/div\u003e\n\u003cp\u003e\u003cstrong\u003eα-Arylation of esters.\u003c\/strong\u003e In one study, palladium(0) with an imidazolinium salt of SIPr as the carbene precursor mediated the coupling of aryl halides with ester enolates to give α-aryl esters. In the same study, the tert-butyl esters of naproxen and flurbiprofen were prepared from tert-butyl propionate and aryl bromides with Pd(dba)₂ and the same carbene precursor.\u003c\/p\u003e\n\u003cdiv style=\"margin:8px 0 18px 0;\"\u003e\n\u003cdiv style=\"display:flex;flex-wrap:wrap;align-items:center;justify-content:flex-start;gap:2px;\"\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\n\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"40px\" height=\"11px\" viewbox=\"0 0 40 11\"\u003e\u003cpath d=\"M 16.5,4.2 L 27.5,4.2\"\u003e\u003c\/path\u003e\u003ctext x=\"4.1\" y=\"10.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eA\u003c\/text\u003e\u003ctext x=\"12.4\" y=\"10.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003er\u003c\/text\u003e\u003ctext x=\"28.1\" y=\"10.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eX\u003c\/text\u003e\u003c\/svg\u003e\n\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003cdiv style=\"font-size:20px;padding:0 4px;align-self:center;\"\u003e+\u003c\/div\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\n\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"93px\" height=\"46px\" viewbox=\"0 0 93 46\"\u003e\u003cpath d=\"M 16.3,28.6 L 28.4,35.6\"\u003e\u003c\/path\u003e\u003cpath d=\"M 28.4,35.6 L 44.8,26.2\"\u003e\u003c\/path\u003e\u003cpath d=\"M 46.2,27.0 L 46.2,14.0\"\u003e\u003c\/path\u003e\u003cpath d=\"M 43.4,27.0 L 43.4,13.9\"\u003e\u003c\/path\u003e\u003cpath d=\"M 44.8,26.2 L 56.9,33.2\"\u003e\u003c\/path\u003e\u003cpath d=\"M 65.3,33.2 L 73.2,28.6\"\u003e\u003c\/path\u003e\u003cpath d=\"M 27.8,35.3 L 28.4,35.6 L 29.3,35.1\"\u003e\u003c\/path\u003e\u003cpath d=\"M 44.0,26.7 L 44.8,26.2 L 45.4,26.5\"\u003e\u003c\/path\u003e\u003ctext x=\"8.5\" y=\"32.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eR\u003c\/text\u003e\u003ctext x=\"41.2\" y=\"13.3\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eO\u003c\/text\u003e\u003ctext x=\"57.5\" y=\"41.6\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eO\u003c\/text\u003e\u003ctext x=\"73.9\" y=\"32.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eR\u003c\/text\u003e\u003ctext x=\"82.1\" y=\"32.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003e′\u003c\/text\u003e\u003c\/svg\u003e\n\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003cdiv style=\"display:flex;flex-direction:column;align-items:center;justify-content:center;min-width:90px;max-width:150px;padding:0 4px;text-align:center;font-size:12px;line-height:1.3;\"\u003e\n\u003cdiv\u003ePd(dba)₂\u003c\/div\u003e\n\u003cdiv style=\"font-size:30px;line-height:1;\"\u003e⟶\u003c\/div\u003e\n\u003cdiv\u003eSIPr carbene precursor\u003c\/div\u003e\n\u003c\/div\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\n\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"96px\" height=\"69px\" viewbox=\"0 0 96 69\"\u003e\u003cpath d=\"M 79.2,30.5 L 67.0,37.6\"\u003e\u003c\/path\u003e\u003cpath d=\"M 67.0,37.6 L 67.0,52.3\"\u003e\u003c\/path\u003e\u003cpath d=\"M 67.0,37.6 L 50.6,28.1\"\u003e\u003c\/path\u003e\u003cpath d=\"M 52.0,28.9 L 52.0,15.7\"\u003e\u003c\/path\u003e\u003cpath d=\"M 49.1,28.9 L 49.2,15.7\"\u003e\u003c\/path\u003e\u003cpath d=\"M 50.6,28.1 L 38.4,35.1\"\u003e\u003c\/path\u003e\u003cpath d=\"M 29.9,35.1 L 19.4,29.0\"\u003e\u003c\/path\u003e\u003cpath d=\"M 51.4,28.5 L 50.6,28.1 L 50.0,28.4\"\u003e\u003c\/path\u003e\u003ctext x=\"79.9\" y=\"34.1\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eR\u003c\/text\u003e\u003ctext x=\"63.4\" y=\"62.6\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eA\u003c\/text\u003e\u003ctext x=\"71.7\" y=\"62.6\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003er\u003c\/text\u003e\u003ctext x=\"47.0\" y=\"15.1\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eO\u003c\/text\u003e\u003ctext x=\"30.5\" y=\"43.5\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eO\u003c\/text\u003e\u003ctext x=\"8.3\" y=\"34.0\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eR\u003c\/text\u003e\u003ctext x=\"16.6\" y=\"34.0\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003e′\u003c\/text\u003e\u003c\/svg\u003e\n\u003c\/div\u003e\n\u003c\/div\u003e\n\u003cp style=\"font-size:12px;margin:4px 0 0 0;\"\u003e\u003cem\u003eGeneral reaction: Ar–X + ester (as its enolate) → α-aryl ester; X = halide.\u003c\/em\u003e\u003c\/p\u003e\n\u003c\/div\u003e\n\u003cp\u003e\u003cstrong\u003eIron-catalysed biaryl coupling.\u003c\/strong\u003e In one study, iron fluorides in combination with SIPr catalysed the cross-coupling of aryl chlorides with aryl Grignard reagents to give biaryls. The authors describe the metal fluoride\/NHC combinations in this work as a route to unsymmetrical biaryls without palladium catalysts or phosphine ligands.\u003c\/p\u003e\n\u003cdiv style=\"margin:8px 0 18px 0;\"\u003e\n\u003cdiv style=\"display:flex;flex-wrap:wrap;align-items:center;justify-content:flex-start;gap:2px;\"\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003cdiv style=\"font:12px sans-serif;padding:0 2px 0 0;margin-left:-2px;\"\u003eAr–MgBr\u003c\/div\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003cdiv style=\"font-size:20px;padding:0 4px;align-self:center;\"\u003e+\u003c\/div\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\n\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"48px\" height=\"11px\" viewbox=\"0 0 48 11\"\u003e\u003cpath d=\"M 20.2,4.2 L 31.8,4.2\"\u003e\u003c\/path\u003e\u003ctext x=\"4.8\" y=\"10.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eA\u003c\/text\u003e\u003ctext x=\"13.1\" y=\"10.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003er\u003c\/text\u003e\u003ctext x=\"17.2\" y=\"10.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003e′\u003c\/text\u003e\u003ctext x=\"32.4\" y=\"10.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eC\u003c\/text\u003e\u003ctext x=\"40.7\" y=\"10.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003el\u003c\/text\u003e\u003c\/svg\u003e\n\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003cdiv style=\"display:flex;flex-direction:column;align-items:center;justify-content:center;min-width:90px;max-width:150px;padding:0 4px;text-align:center;font-size:12px;line-height:1.3;\"\u003e\n\u003cdiv\u003eiron fluoride\u003c\/div\u003e\n\u003cdiv style=\"font-size:30px;line-height:1;\"\u003e⟶\u003c\/div\u003e\n\u003cdiv\u003eSIPr\u003c\/div\u003e\n\u003c\/div\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\n\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"49px\" height=\"11px\" viewbox=\"0 0 49 11\"\u003e\u003cpath d=\"M 17.4,4.2 L 28.5,4.2\"\u003e\u003c\/path\u003e\u003ctext x=\"5.0\" y=\"10.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eA\u003c\/text\u003e\u003ctext x=\"13.3\" y=\"10.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003er\u003c\/text\u003e\u003ctext x=\"29.0\" y=\"10.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eA\u003c\/text\u003e\u003ctext x=\"37.3\" y=\"10.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003er\u003c\/text\u003e\u003ctext x=\"41.5\" y=\"10.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003e′\u003c\/text\u003e\u003c\/svg\u003e\n\u003c\/div\u003e\n\u003c\/div\u003e\n\u003cp style=\"font-size:12px;margin:4px 0 0 0;\"\u003e\u003cem\u003eGeneral reaction: Ar–MgBr + Ar′–Cl → Ar–Ar′ (unsymmetrical biaryl).\u003c\/em\u003e\u003c\/p\u003e\n\u003c\/div\u003e\n\u003cp\u003e\u003cstrong\u003eChemoselective Suzuki–Miyaura coupling.\u003c\/strong\u003e In the palladium-catalysed Suzuki–Miyaura coupling of chloroaryl triflates, one study found that SIPr as ligand led to selective coupling at the chloride. With SIMes, the related carbene with 2,4,6-trimethylphenyl groups, the coupling was selective for the triflate.\u003c\/p\u003e\n\u003cdiv style=\"margin:8px 0 18px 0;\"\u003e\n\u003cdiv style=\"display:flex;flex-wrap:wrap;align-items:center;justify-content:flex-start;gap:2px;\"\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\n\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"116px\" height=\"63px\" viewbox=\"0 0 116 63\"\u003e\u003cpath d=\"M 21.2,43.2 L 25.8,40.5\"\u003e\u003c\/path\u003e\u003cpath d=\"M 38.9,36.3 L 48.2,41.7\"\u003e\u003c\/path\u003e\u003cpath d=\"M 56.7,41.7 L 64.7,37.1\"\u003e\u003c\/path\u003e\u003cpath d=\"M 71.5,42.0 L 74.7,47.6\"\u003e\u003c\/path\u003e\u003cpath d=\"M 74.0,40.5 L 77.2,46.1\"\u003e\u003c\/path\u003e\u003cpath d=\"M 67.7,29.7 L 64.4,24.1\"\u003e\u003c\/path\u003e\u003cpath d=\"M 65.2,31.1 L 62.0,25.5\"\u003e\u003c\/path\u003e\u003cpath d=\"M 73.1,32.2 L 85.4,25.1\"\u003e\u003c\/path\u003e\u003cpath d=\"M 85.4,25.1 L 79.7,15.2\"\u003e\u003c\/path\u003e\u003cpath d=\"M 85.4,25.1 L 91.0,15.2\"\u003e\u003c\/path\u003e\u003cpath d=\"M 85.4,25.1 L 97.6,32.1\"\u003e\u003c\/path\u003e\u003ctext x=\"10.1\" y=\"50.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eC\u003c\/text\u003e\u003ctext x=\"18.4\" y=\"50.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003el\u003c\/text\u003e\u003ctext x=\"26.4\" y=\"40.6\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eA\u003c\/text\u003e\u003ctext x=\"34.7\" y=\"40.6\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003er\u003c\/text\u003e\u003ctext x=\"48.8\" y=\"50.1\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eO\u003c\/text\u003e\u003ctext x=\"65.3\" y=\"40.6\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eS\u003c\/text\u003e\u003ctext x=\"74.8\" y=\"57.1\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eO\u003c\/text\u003e\u003ctext x=\"55.8\" y=\"24.1\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eO\u003c\/text\u003e\u003ctext x=\"72.2\" y=\"14.6\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eF\u003c\/text\u003e\u003ctext x=\"91.3\" y=\"14.6\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eF\u003c\/text\u003e\u003ctext x=\"98.3\" y=\"40.6\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eF\u003c\/text\u003e\u003c\/svg\u003e\n\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003cdiv style=\"font-size:20px;padding:0 4px;align-self:center;\"\u003e+\u003c\/div\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\n\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"70px\" height=\"46px\" viewbox=\"0 0 70 46\"\u003e\u003cpath d=\"M 21.1,34.6 L 31.5,28.6\"\u003e\u003c\/path\u003e\u003cpath d=\"M 35.8,22.0 L 35.8,13.9\"\u003e\u003c\/path\u003e\u003cpath d=\"M 40.0,28.6 L 47.9,33.3\"\u003e\u003c\/path\u003e\u003ctext x=\"5.7\" y=\"41.6\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eA\u003c\/text\u003e\u003ctext x=\"14.0\" y=\"41.6\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003er\u003c\/text\u003e\u003ctext x=\"18.1\" y=\"41.6\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003e′\u003c\/text\u003e\u003ctext x=\"32.2\" y=\"32.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eB\u003c\/text\u003e\u003ctext x=\"32.2\" y=\"13.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eO\u003c\/text\u003e\u003ctext x=\"40.5\" y=\"13.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eH\u003c\/text\u003e\u003ctext x=\"48.5\" y=\"41.7\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eO\u003c\/text\u003e\u003ctext x=\"56.8\" y=\"41.7\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eH\u003c\/text\u003e\u003c\/svg\u003e\n\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\u003cdiv style=\"display:flex;flex-direction:column;align-items:center;justify-content:center;min-width:90px;max-width:150px;padding:0 4px;text-align:center;font-size:12px;line-height:1.3;\"\u003e\n\u003cdiv\u003ePd, SIPr\u003c\/div\u003e\n\u003cdiv style=\"font-size:30px;line-height:1;\"\u003e⟶\u003c\/div\u003e\n\u003cdiv\u003e\u003c\/div\u003e\n\u003c\/div\u003e\u003c\/div\u003e\n\u003cdiv style=\"display:flex;align-items:center;\"\u003e\n\u003csvg role=\"img\" style=\"max-width:100%;height:auto;\" xmlns=\"http:\/\/www.w3.org\/2000\/svg\" fill=\"none\" stroke=\"#000\" stroke-width=\"1.6\" width=\"121px\" height=\"63px\" viewbox=\"0 0 121 63\"\u003e\u003cpath d=\"M 25.8,43.1 L 30.3,40.5\"\u003e\u003c\/path\u003e\u003cpath d=\"M 43.4,36.3 L 52.7,41.7\"\u003e\u003c\/path\u003e\u003cpath d=\"M 61.2,41.7 L 69.2,37.1\"\u003e\u003c\/path\u003e\u003cpath d=\"M 76.0,42.0 L 79.3,47.6\"\u003e\u003c\/path\u003e\u003cpath d=\"M 78.5,40.5 L 81.7,46.1\"\u003e\u003c\/path\u003e\u003cpath d=\"M 72.2,29.7 L 69.0,24.1\"\u003e\u003c\/path\u003e\u003cpath d=\"M 69.7,31.1 L 66.5,25.5\"\u003e\u003c\/path\u003e\u003cpath d=\"M 77.6,32.2 L 89.9,25.1\"\u003e\u003c\/path\u003e\u003cpath d=\"M 89.9,25.1 L 84.2,15.2\"\u003e\u003c\/path\u003e\u003cpath d=\"M 89.9,25.1 L 95.6,15.2\"\u003e\u003c\/path\u003e\u003cpath d=\"M 89.9,25.1 L 102.1,32.1\"\u003e\u003c\/path\u003e\u003ctext x=\"10.4\" y=\"50.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eA\u003c\/text\u003e\u003ctext x=\"18.7\" y=\"50.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003er\u003c\/text\u003e\u003ctext x=\"22.8\" y=\"50.2\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003e′\u003c\/text\u003e\u003ctext x=\"30.9\" y=\"40.6\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eA\u003c\/text\u003e\u003ctext x=\"39.2\" y=\"40.6\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003er\u003c\/text\u003e\u003ctext x=\"53.4\" y=\"50.1\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eO\u003c\/text\u003e\u003ctext x=\"69.8\" y=\"40.6\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eS\u003c\/text\u003e\u003ctext x=\"79.3\" y=\"57.1\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eO\u003c\/text\u003e\u003ctext x=\"60.3\" y=\"24.1\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eO\u003c\/text\u003e\u003ctext x=\"76.8\" y=\"14.6\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eF\u003c\/text\u003e\u003ctext x=\"95.8\" y=\"14.6\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eF\u003c\/text\u003e\u003ctext x=\"102.8\" y=\"40.6\" style=\"font:12px sans-serif;fill:#000;stroke:none\"\u003eF\u003c\/text\u003e\u003c\/svg\u003e\n\u003c\/div\u003e\n\u003c\/div\u003e\n\u003cp style=\"font-size:12px;margin:4px 0 0 0;\"\u003e\u003cem\u003eGeneral reaction: Cl–Ar–OTf + Ar′–B(OH)₂ → Ar′–Ar–OTf; with SIPr, coupling is selective for the chloride.\u003c\/em\u003e\u003c\/p\u003e\n\u003c\/div\u003e\n\u003c\/div\u003e\u003c\/div\u003e\n\u003c\/div\u003e\n\u003cdiv style=\"margin-bottom: 28px;\"\u003e\n\u003cdiv style=\"background: #002147; padding: 10px 20px; margin-bottom: 0;\"\u003e\u003ch3 style=\"margin: 0; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; font-size: 0.70em; font-weight: bold; letter-spacing: 0.12em; text-transform: uppercase; color: #fff;\"\u003eShipping Destinations\u003c\/h3\u003e\u003c\/div\u003e\n\u003cdiv style=\"border: 1px solid #e4e8f0; border-top: none; padding: 12px 16px; font-family: 'Helvetica Neue', Helvetica, Arial, sans-serif; font-size: 0.95em;\"\u003e\u003cul style=\"margin: 0; padding: 0; list-style: none;\"\u003e\n\u003cli style=\"padding: 5px 0; border-bottom: 1px solid #f0f0f0;\"\u003e\n\u003cspan style=\"display: inline-block; width: 7px; height: 7px; background: #002147; border-radius: 50%; margin-right: 10px; vertical-align: middle;\"\u003e\u003c\/span\u003eEU \u0026amp; UK: Priority delivery, 2–5 business days.\u003c\/li\u003e\n\u003cli style=\"padding: 5px 0; border-bottom: 1px solid #f0f0f0;\"\u003e\n\u003cspan style=\"display: inline-block; width: 7px; height: 7px; background: #002147; border-radius: 50%; margin-right: 10px; vertical-align: middle;\"\u003e\u003c\/span\u003eUnited States (DDP): 3–7 business days, duties and taxes prepaid.\u003c\/li\u003e\n\u003cli style=\"padding: 5px 0; border-bottom: 1px solid #f0f0f0;\"\u003e\n\u003cspan style=\"display: inline-block; width: 7px; height: 7px; background: #002147; border-radius: 50%; margin-right: 10px; vertical-align: middle;\"\u003e\u003c\/span\u003eEFTA Countries (DDP): 3–7 business days, duties and taxes prepaid.\u003c\/li\u003e\n\u003cli style=\"padding: 5px 0; border-bottom: 1px solid #f0f0f0;\"\u003e\n\u003cspan style=\"display: inline-block; width: 7px; height: 7px; background: #002147; border-radius: 50%; margin-right: 10px; vertical-align: middle;\"\u003e\u003c\/span\u003eWorldwide: 7–14 business days, selected locations.\u003c\/li\u003e\n\u003c\/ul\u003e\u003c\/div\u003e\n\u003c\/div\u003e","brand":"NorrChemica™","offers":[{"title":"250 mg","offer_id":55166901059921,"sku":"NOR-258278250-250mg","price":34.2,"currency_code":"EUR","in_stock":true},{"title":"1.0 g","offer_id":55166901092689,"sku":"NOR-258278250-1g","price":49.2,"currency_code":"EUR","in_stock":true},{"title":"5.0 g","offer_id":55166901125457,"sku":"NOR-258278250-5g","price":74.2,"currency_code":"EUR","in_stock":true},{"title":"10 g","offer_id":55166901158225,"sku":"NOR-258278250-10g","price":98.2,"currency_code":"EUR","in_stock":true},{"title":"25 g","offer_id":55166901190993,"sku":"NOR-258278250-25g","price":179.8,"currency_code":"EUR","in_stock":true},{"title":"50 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