Light-Mediated Reductive Debromination of Unactivated Alkyl and Aryl Bromides

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• 作者：James J. Devery III ; John D. Nguyen ; Chunhui Dai ; Corey R. J. Stephenson
• 刊名：ACS Catalysis
• 出版年：2016
• 出版时间：September 2, 2016
• 年：2016
• 卷：6
• 期：9
• 页码：5962-5967
• 全文大小：501K
• 年卷期：0
• ISSN：2155-5435

文摘

Cleavage of carbon–halogen bonds via either single-electron reduction or atom transfer is a powerful transformation in the construction of complex molecules. In particular, mild, selective hydrodehalogenations provide an excellent follow-up to the application of halogen atoms as directing groups or the utilization of atom transfer radical addition (ATRA) chemistry for the production of hydrocarbons. Here we combine the mechanistic properties of photoredox catalysis and silane-mediated atom transfer chemistry to accomplish the hydrodebromination of carbon–bromide bonds. The resulting method is performed under visible light irradiation in an open vessel and is capable of the efficient reduction of a variety of unactivated alkyl and aryl substrates.