Journal of the American Chemical Society
Journal of the American Chemical Society
4 years ago

Directed β C–H Amination of Alcohols via Radical Relay Chaperones

Directed β C–H Amination of Alcohols via Radical Relay Chaperones
Kohki M. Nakafuku, David A. Nagib, Ethan A. Wappes
A radical-mediated strategy for β C–H amination of alcohols has been developed. This approach employs a radical relay chaperone, which serves as a traceless director that facilitates selective C–H functionalization via 1,5-hydrogen atom transfer (HAT) and enables net incorporation of ammonia at the β carbon of alcohols. The chaperones presented herein enable direct access to imidate radicals, allowing their first use for H atom abstraction. A streamlined protocol enables rapid conversion of alcohols to their β-amino analogs (via in situ conversion of alcohols to imidates, directed C–H amination, and hydrolysis to NH2). Mechanistic experiments indicate HAT is rate-limiting, whereas intramolecular amination is product- and stereo-determining.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b05214

DOI: 10.1021/jacs.7b05214

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