Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 1, Pages 22-25Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b09744
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Funding
- NIH [R01 GM100143, F32 GM113399, S10 OD020022]
- NSF [CHE-1048642]
- Merck Research Laboratories
- SIOC fellowship
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM100143, F32GM113399] Funding Source: NIH RePORTER
- OFFICE OF THE DIRECTOR, NATIONAL INSTITUTES OF HEALTH [S10OD020022] Funding Source: NIH RePORTER
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An electrochemical method has been developed for selective benzylic iodination of methylarenes. The reactions feature the first use of N-hydroxyphthalimide as an electrochemical mediator for C-H oxidation to nonoxygenated products. The method provides the basis for direct (in situ) or sequential benzylation of diverse nucleophiles using methylarenes as the alkylating agent. The hydrogen-atom transfer mechanism for C-H iodination allows C-H oxidation to proceed with minimal dependence on the substrate electronic properties and at electrode potentials 0.5-1.2 V lower than that of direct electrochemical C-H oxidation.
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