Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 1, Pages 58-61Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b10529
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Funding
- NIH [1R35GM125029]
- Sloan Research Foundation
- University of Illinois
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R35GM125029] Funding Source: NIH RePORTER
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Copper-catalyzed intermolecular carboamination of alkenes with alpha-halocarbonyls and amines is presented with 42 examples. Electron rich, electron poor, and internal styrenes, as well as alpha-olefins, are function-alized with alpha-halocarbonyls and aryl or aliphatic amines. Mechanistic investigations suggest the reaction is proceeding through addition of a carbon-centered radical across an olefin followed by oxidation to form a 5-membered oxocarbenium intermediate and subsequent nucleophilic ring opening to forge the C-N bond.
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