Overcoming Electron-Withdrawing and Product-Inhibition Effects by Organocatalytic Aerobic Oxidation of Alkylpyridines and Related Alkylheteroarenes to Ketones

An organocatalyzed aerobic benzylic C–H oxidation of alkyl and aryl heterocycles has been developed. This transition metal-free method is able to overcome the electron-withdrawing effect as well as product-inhibition effects in heterobenzylic radical oxidation. A variety of ketones bearing N-heteroc...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-03, Vol.85 (5), p.3942-3948
Main Authors: Wang, Hua, Liu, Jie, Qu, Jian-Ping, Kang, Yan-Biao
Format: Article
Language:English
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Summary:An organocatalyzed aerobic benzylic C–H oxidation of alkyl and aryl heterocycles has been developed. This transition metal-free method is able to overcome the electron-withdrawing effect as well as product-inhibition effects in heterobenzylic radical oxidation. A variety of ketones bearing N-heterocyclic groups could be prepared under relatively mild conditions with moderate to high yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b03205