期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 31, 页码 9060-9064出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201603399
关键词
amides; amines; peroxides; radicals; reaction mechanisms
资金
- School of Chemistry, University of Lincoln, UK
- Grants-in-Aid for Scientific Research [16K13942] Funding Source: KAKEN
An efficient amidation method between readily available 1,1-dicyanoalkanes and either chiral or nonchiral amines was realized simply with molecular oxygen and a carbonate base. This oxidative protocol can be applied to both sterically and electronically challenging substrates in a highly chemoselective, practical, and rapid manner. The use of cyclopropyl and thioether substrates support the radical formation of alpha-peroxy malononitrile species, which can cyclize to dioxiranes that can monooxygenate malononitrile alpha-carbanions to afford activated acyl cyanides capable of reacting with amine nucleophiles.
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