Allylboronic Esters as Acceptors in Radical Addition, Boron 1,2-Migration, and Trapping Cascades

Abstract

Radical 1,3-carboheteroarylation and 1,3-hydroalkylation of allylboronic esters comprising a 1,2-boron shift is reported. Allylboronic esters are generally used in synthesis as allylation reagents, where the boronic ester moiety gets lost. In the introduced cascades, alkylboronic esters are obtained with the boron entity remaining in the product. The carboheteroarylation of the allylboronic esters are conducted without a metal catalyst, and the 1,3-hydroalkylation is achieved using iron catalysis. Both reactions work efficiently under mild conditions.

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