Presented in this work is a novel methodology for the synthesis of selenated benzofurans (or benzothiophenes) via AgNO-catalyzed radical cyclization of 2-alkynylanisoles (or 2-alkynylthioanisoles), Se powder, and arylboronic acids. This method enables the construction of a benzofuran (benzothiophene) ring, two C-Se bonds, and a C-O(S) bond as well as the cleavage of a C-O(S) bond in a single step. Preliminary mechanistic studies imply that the AgNO-catalyzed cyclization proceeds via an aryl selenium radical intermediate.
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