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可见光促进的通过 O-α-sp(3) C-H 断裂实现的烷基苄基醚转化为烷基酯或醇。

Visible-light-promoted conversion of alkyl benzyl ether to alkyl ester or alcohol via O-α-sp(3) C-H cleavage.

机构信息

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering, and Materials Science, Soochow University, 199 RenAi Road, Suzhou, Jiangsu 215123, China.

出版信息

Org Lett. 2015 Apr 17;17(8):1954-7. doi: 10.1021/acs.orglett.5b00663. Epub 2015 Apr 2.

Abstract

A mild and high-yielding visible-light-promoted conversion of alkyl benzyl ethers to the alkyl esters or alkyl alcohols was developed. Mechanistic studies provided evidence for a radical chain reaction involving the homolytic cleavage of O-α-sp(3) C-H bonds in the substrate as one of the propagation steps. We propose that α-bromoethers are key intermediates in the transformation.

摘要

发展了一种温和高产的可见光促进的烷基苄基醚向烷基酯或烷基醇的转化方法。机理研究为涉及底物中 O-α-sp(3) C-H 键均裂的自由基链式反应提供了证据,这是增长步骤之一。我们提出α-溴代醚是转化中的关键中间体。

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