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γ-二卤代环丙烷的可切换发散式电化学加氢脱卤反应

Switchable Divergent Electrochemical Hydrodehalogenation of -Dihalocyclopropanes.

作者信息

Pan Jiayu, Qu Haoqi, Li Yuanmeng, Bu XiaoLi, Deng HongPing, Gong Hao, Ma Mengtao, Xu Li, Xue Fei

机构信息

Institute of Material Physics & Chemistry, College of Science, Nanjing Forestry University, Nanjing 210037, P. R. China.

Co-Innovation Center for Sustainable Forestry in Southern China, Nanjing Forestry University, Nanjing 210037, P. R. China.

出版信息

J Org Chem. 2024 Nov 15;89(22):16929-16935. doi: 10.1021/acs.joc.4c01748. Epub 2024 Oct 29.

Abstract

A comprehensive and effective electrochemical methodology is introduced for the diverse hydrodechlorination of -dichlorocyclopropanes and the ring cleavage hydrodefluorination of -difluorocyclopropanes under uniform electrochemical conditions. Moreover, the water content allows for the adjustable monohydrodechlorination or dihydrodechlorination of -dichlorocyclopropanes with exceptional chemoselectivity. Additionally, the mildness and practicality of this protocol facilitate its application to the late-stage functionalization of bioactive molecules. Mechanistic analyses suggest that the proton source may originate from acetonitrile.

摘要

介绍了一种全面有效的电化学方法,用于在统一的电化学条件下对α-二氯环丙烷进行多种加氢脱氯反应以及对α-二氟环丙烷进行开环加氢脱氟反应。此外,含水量可实现α-二氯环丙烷具有优异化学选择性的单加氢脱氯或二加氢脱氯反应。此外,该方法的温和性和实用性便于其应用于生物活性分子的后期官能团化反应。机理分析表明质子源可能来自乙腈。

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