期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 20, 页码 13065-13072出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02052
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资金
- National Institutes of Health [NIH R35 GM119812]
- National Science Foundation [NSF CAREER 1654656]
- American Chemical Society Petroleum Research Fund
- NIH [S10-RR027172]
- NSF GRFP Fellowship
The design of a radical relay chaperone to promote selective C-H functionalizations is described. A saccharin-based imine was found to be uniquely suited to effect C-H amination of alcohols via an in situ generated hemiaminal. This radical chaperone facilitates the mild generation of an N-centered radical while also directing its regioselective H atom transfer (HAT) to the beta carbon of an alcohol. Upon beta C-H halogenation, aminocyclization, and reductive cleavage, an NH2 is formally added vicinal to an alcohol. The development, synthetic utility, and chemo-, regio-, and stereoselectivity of this imine chaperone-mediated C-H amination is presented herein.
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