Science of Synthesis

Gagnon, A.; Benoit, E.; Le Roch, A., Science of Synthesis Knowledge Updates, (2018) 4, 66.

Arylbismuth compounds have been used to arylate carbon, oxygen, nitrogen, sulfur, and selenium nucleophiles, leading to C—C, C—O, C—N, C—S, and C—Se bond formation. Many reviews have been published on arylation reactions involving organobismuth compounds.[‌26‌,‌28‌,‌303‌–‌306‌] While the first arylation methods usually relied on pentavalent organobismuthines, more recent protocols operate directly with triarylbismuth analogues. Arylation methods involving pentavalent reagents can often be performed in the absence of a catalyst; however, the addition of a copper catalyst greatly accelerates the arylation process. Arylation reactions involving triarylbismuth compounds usually do not proceed in the absence of a catalyst. Copper(II) dicarboxylates are most frequently used as catalysts with triarylbismuthines. Stronger co-oxidants such as (diacetoxyiodo)benzene have also been used in arylation reactions with triarylbismuthines. Usually, at least 1 equivalent of the organobismuth compound is required for C-, O-, N-, S- and Se-arylation reactions as only one aryl group is transferred.

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