Palladium catalyzed acetoxylation of benzylic C-H bonds using a bidentate picolinamide directing group
Tao Cheng1, Weiyu Yin, Yi Zhang
1Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University, Shenzhen Graduate School, Shenzhen, 518055, China. huangyong@pkusz.edu.cn.
Abstract:
A general palladium catalyzed acetoxylation of benzylic C-H bonds has been developed. Picolinamides serve as an excellent directing group for the C-H activation of benzylic methyls. A wide range of 2-amino benzyl alcohol analogues were synthesized in good yields. The products demonstrated broad synthetic utilities toward various benzo-fused heterocycles. Mechanistic studies revealed the key rate-limiting C-H insertion step, which could be affected by the substitution pattern of the parent arene.
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