Benzyne Polyfunctionalization via a Tandem C-C σ-Bond Insertion and Photo-Nazarov Cyclization.

Org Lett

School of Chemistry and Chemical Engineering, Chongqing University, 174 Shazheng Street, Chongqing 400030, P. R. China.

Published: October 2022

A tandem benzyne C-C σ-bond insertion reaction and photo-Nazarov cyclization protocol was developed, leading to the formation of three C-C bonds at consecutive positions of a benzene ring with concomitant assembly of a 6-5-6 tricyclic ring system. When 3-silylbenzyne precursors were employed, a tandem process involving a benzyne C-C σ-bond insertion, a photo-Nazarov cyclization, and a 1,3-silyl group migration was observed, which could produce 1,2,3,5-tetrasubstituted benzenes.

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http://dx.doi.org/10.1021/acs.orglett.2c02652DOI Listing

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