Scalable, Electrochemical Oxidation of Unactivated C-H Bonds

Journal of the American Chemical Society
Yu KawamataPhil S Baran

Abstract

A practical electrochemical oxidation of unactivated C-H bonds is presented. This reaction utilizes a simple redox mediator, quinuclidine, with inexpensive carbon and nickel electrodes to selectively functionalize "deep-seated" methylene and methine moieties. The process exhibits a broad scope and good functional group compatibility. The scalability, as illustrated by a 50 g scale oxidation of sclareolide, bodes well for immediate and widespread adoption.

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Citations

Mar 7, 2018·Angewandte Chemie·Nicolas SauermannLutz Ackermann
Aug 24, 2017·Angewandte Chemie·Ming YanPhil S Baran
Jan 18, 2018·Chemistry : a European Journal·Diego VidalMiquel Costas
Jan 3, 2018·Angewandte Chemie·Anton WiebeSiegfried R Waldvogel
Apr 6, 2018·Chemical Science·Florian BartelsMathias Christmann
Jun 7, 2018·Organic & Biomolecular Chemistry·Stéphane SengmanyEric Léonel
Jun 19, 2018·Chemical Society Reviews·Markus D Kärkäs
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Jun 15, 2018·Chemistry : a European Journal·Youai QiuLutz Ackermann
Nov 1, 2018·Chemistry : a European Journal·Shou-Kun ZhangLutz Ackermann
Jan 3, 2019·Chemical Communications : Chem Comm·Jason A MarkoWei Liu
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Mar 26, 2019·Angewandte Chemie·Qinglin ZhangChang Guo
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