Bromide-Catalyzed Radical Cyclization of Biarylboronic Acids and Se/Te Powder

Herein, a metal-free and versatile strategy was successfully reported for the divergent synthesis of various functionalized dibenzo[b,d]selenophenes, dibenzo[b,d]tellurophenes, and phenoxaselenines in moderate to excellent yields in one-pot. This method utilized commercially available, cheap, and sustainable ammonium bromide as the catalyst to promote the radical cyclization of biarylboronic acids with elemental Se/Te. Comparatively, this method was highlighted by its readily available starting material, broad substrate scope, simple catalytic system, easy operation, good safety, being strongly oxidant-free, and easily scalable. The preliminary mechanistic experiments suggested that this transformation could possibly proceed via a radical pathway.

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