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Palladium-Catalyzed Difunctionalization of Norbornenes via Arylation and Alkynylation

Yijun Shi, Chong-Lei Ji* and Chengwei Liu*

*Zhejiang University, 38 Zheda Road, Hangzhou 310027; Shanghai University, 99 Shangda Road, Shanghai 200444, China, Email: chjiclzju.edu.cn, chengwei_liushu.edu.cn

Y. Shi, C.-L. Ji, C. Liu, J. Org. Chem., 2023, 88, 261-271.

DOI: 10.1021/acs.joc.2c02295


Abstract

Pd(OAc)2/PCy3HBF4 catalyzes an addition of aryl halides and alkynes to norbornenes to construct saturated bridged C-C bonds. This efficient difunctionalization of norbornenes includes C-X/C-H bond cleavage and highly selective C(sp3)-C(sp2)/C(sp3)-C(sp) bond formation. The reaction offers broad substrate scope and excellent functional group tolerance.

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proposed mechanism



Key Words

cyclohexanes, cyclopentanes, multicomponent reactions


ID: J42-Y2023