Potassium (3,4-Dichlorophenyl)trifluoroborate

Technical Specifications

Product Description & Scientific Applications

Potassium (3,4-dichlorophenyl)trifluoroborate is an aryltrifluoroborate salt and a bench-stable surrogate for 3,4-dichlorophenylboronic acid. Its boron is four-coordinate, anionic and not Lewis acidic, and the crystalline solid is stable to air and moisture.

Slow boronate release. The two ring chlorines withdraw electron density which slows down trifluoroborate solvolysis and the resulting release of the active boronate.

Suzuki–Miyaura coupling. The salt is a 3,4-dichlorophenyl donor for Suzuki–Miyaura cross-coupling, transmetalating to palladium as the released boronate and coupling with aryl and heteroaryl bromides to give 3,4-dichlorobiaryls. The deactivated ring reacts efficiently at a low PdCl₂(dppf) loading.

Bifunctional handle. The ring carries two aryl carbon–chlorine bonds which resist oxidative addition to palladium(0) under standard ligands and therefore survive coupling at the boron. Each remains a latent handle for further cross-coupling, so the two sites together support sequential functionalisation.

Further applications

• Rhodium conjugate addition. Under rhodium catalysis with a chiral diene ligand and triethylamine, the salt adds 1,4 to α,β-unsaturated ketones, the asymmetric variant proceeding at room temperature.
• C–H arylation. With palladium(II) and copper(II) acetate in acetic acid, the salt arylates indoles directly at C2 to give 2-arylindoles, with no prehalogenated partner required.
• Ketone synthesis. Under rhodium catalysis the salt couples with aromatic aldehydes to give aryl ketones, with acetone accepting the hydride.
• Imine arylation. Under rhodium catalysis the salt adds to N-sulfonyl ketimines, the asymmetric variant giving chiral amines.
• Petasis reaction. Acid promotes addition to imines and enamines, building amines with no metal catalyst.
• Chan–Lam coupling. Under copper(II) acetate and oxygen the salt couples with amines and anilines to give arylamines, or with alcohols and phenols to give aryl ethers.

Further Reading

For boronic acids, boronic esters, protodeboronation, boroxine content, and Suzuki–Miyaura reagent selection, see NorrChemica's Lab Journal guide: Choosing Your Boron Source for Suzuki–Miyaura Coupling

Shipping Destinations

• EU & UK: Priority delivery, 2–5 business days.
• United States (DDP): 3–7 business days, duties and taxes prepaid.
• EFTA Countries (DDP): 3–7 business days, duties and taxes prepaid.
• Worldwide: 7–14 business days, selected locations.