Visible-Light-Promoted Conversion of Alkyl Benzyl Ether to Alkyl Ester or Alcohol via O-α-sp³ C-H Cleavage

Ping Lu, Tianyuan Hou, Xiangyong Gu and Pixu Li*

*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, Email: lipixusuda.edu.cn

P. Lu, T. Hou, X. Gu, P. Li, Org. Lett., 2015, 17, 1954-1957.

DOI: 10.1021/acs.orglett.5b00663

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Abstract

A mild and high-yielding visible-light-promoted reaction of alkyl benzyl ethers provided alkyl esters or alkyl alcohols via radical chain reaction involving the homolytic cleavage of O-α-sp³ C-H bonds in the substrate as one of the propagation steps. α-Bromoethers are key intermediates in the transformation.

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proposed reaction pathway

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Key Words

benzyl ethers

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ID: J54-Y2015