4,4'-Di-tert-butyl-2,2'-bipyridine (dtbpy)

Technical Specifications

Product Description & Scientific Applications

4,4'-Di-tert-butyl-2,2'-bipyridine (dtbpy, dtbbpy) is 2,2'-bipyridine carrying a tert-butyl group on each 4-position. The substituents do two things. They donate electron density, shifting the reduction of the resulting metal complex to a more negative potential than the unsubstituted parent. They also make those complexes soluble in organic solvents. That is why dtbpy replaces bipyridine in most catalytic work. The white crystalline solid is stored under inert gas.

Iridium C–H borylation. Combined with [Ir(OMe)(COD)]₂, it gives the catalyst that borylates C–H bonds directly, using bis(pinacolato)diboron as the boron source. Thiophenes, furans and pyrroles are borylated at room temperature under these conditions.

Photoredox complexes. It is the ancillary ligand of the heteroleptic iridium(III) photocatalysts, among them [Ir(dF(CF₃)ppy)₂(dtbpy)]PF₆ and [Ir(ppy)₂(dtbbpy)]PF₆, used for visible-light reductive coupling.

Nickel cross-coupling. On nickel it supports cross-electrophile coupling of aryl bromides with alkyl bromides under manganese or zinc reduction. It also supports photochemical decarboxylative coupling of aryl bromides with alkyl carboxylic acids.

Dual photoredox catalysis. As the nickel-bound ligand in nickel–ruthenium systems it enables 1,4-difunctionalisation of 1,3-enynes with aryl halides and sodium sulfinates.

Rhenium carbon dioxide reduction. In the reduced complex [Re(bpytBu)(CO)₃]⁻ the added electron localises on the bipyridine ligand rather than on the metal.

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