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

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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… Click to show full abstract

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.

Keywords: bond insertion; photo nazarov; nazarov cyclization

Journal Title: Organic letters
Year Published: 2022

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