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电化学促进的烯烃与羟基及有机三氟硼酸盐的碳羟基化反应

Electrochemically Enabled Carbohydroxylation of Alkenes with HO and Organotrifluoroborates.

作者信息

Xiong Peng, Long Hao, Song Jinshuai, Wang Yaohui, Li Jian-Feng, Xu Hai-Chao

机构信息

State Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, Innovative Collaboration Center of Chemistry for Energy Materials, and College of Chemistry and Chemical Engineering , Xiamen University , Xiamen 361005 , P. R. China.

Fujian Institute of Research on Structure of Matter, Chinese Academy of Sciences , Fuzhou 350002 , P. R. China.

出版信息

J Am Chem Soc. 2018 Dec 5;140(48):16387-16391. doi: 10.1021/jacs.8b08592. Epub 2018 Nov 5.

DOI:10.1021/jacs.8b08592
PMID:30384602
Abstract

Unprecedented hydroxy-alkynylation and -alkenylation reactions of arylalkenes have been developed through electrochemically enabled addition of an organotrifluoroborate reagent and HO across the double bond of the alkene. The use of electrochemistry to promote these oxidative alkene 1,2-difunctionalization reactions not only obviates the need for transition-metal catalysts and oxidizing reagents but also ensures high regio- and chemoselectivity to afford homopropargylic or homoallylic alcohols. The possibility of extending the electrochemical alkene difunctionalization strategy to other alkene carbo-heterofunctionalization reactions has been demonstrated.

摘要

通过电化学促进有机三氟硼酸盐试剂和HO跨烯烃双键的加成,开发了前所未有的芳基烯烃羟基炔基化和烯基化反应。利用电化学促进这些氧化烯烃1,2-双官能团化反应,不仅消除了对过渡金属催化剂和氧化剂的需求,而且确保了高区域选择性和化学选择性,以提供高炔丙基醇或高烯丙基醇。已经证明了将电化学烯烃双官能团化策略扩展到其他烯烃碳-杂官能团化反应的可能性。

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