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氢转移策略促进酮铃木-宫浦偶联反应中未受应变 C(O)-C 键的选择性活化。

Selective Activation of Unstrained C(O)-C Bond in Ketone Suzuki-Miyaura Coupling Reaction Enabled by Hydride-Transfer Strategy.

机构信息

College of Chemistry, Sichuan University, 29 Wangjiang Road, Chengdu 610064, P. R. China.

West China School of Public Health and West China Fourth Hospital and State Key Laboratory of Biotherapy, Sichuan University, Chengdu 610041, P. R. China.

出版信息

Org Lett. 2022 Feb 18;24(6):1372-1377. doi: 10.1021/acs.orglett.2c00110. Epub 2022 Feb 7.

Abstract

A Rh(I)-catalyzed ketone Suzuki-Miyaura coupling reaction of benzylacetone with arylboronic acid is developed. Selective C(O)-C bond activation, which employs aminopyridine as a temporary directing group and ethyl vinyl ketone as a hydride acceptor, occurs on the alkyl chain containing a β-position hydrogen. A series of acetophenone products were obtained in yields up to 75%.

摘要

发展了一种 Rh(I)催化的酮Suzuki-Miyaura 偶联反应,该反应以苄基丙酮和芳基硼酸为底物。通过选择性的 C(O)-C 键活化,利用氨基吡啶作为临时导向基团,乙烯基酮作为氢受体,在含有β-位氢的烷基链上发生反应。一系列苯乙酮产物的收率高达 75%。

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