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J Am Chem Soc. 2017 Jun 7;139(22):7448-7451. doi: 10.1021/jacs.7b03539. Epub 2017 May 23.

Scalable, Electrochemical Oxidation of Unactivated C-H Bonds.

Author information

1
Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
2
Asymchem Life Science (Tianjin), Tianjin Economic-Technological Development Zone , Tianjin 300457, China.
3
Discovery Sciences, Medicine Design, Pfizer Global Research and Development , 445 Eastern Point Road, Groton, Connecticut 06340, United States.

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.

PMID:
28510449
PMCID:
PMC5465511
DOI:
10.1021/jacs.7b03539
[Indexed for MEDLINE]
Free PMC Article

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