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

Ethan A. Wappes, Kohki M. Nakafuku and David A. Nagib*

*Department of Chemistry and Biochemistry, The Ohio State University, Columbus, Ohio 43210, United States, Email:

E. A. Wappes, K. M. Nakafuku, D. A. Nagib, J. Am. Chem. Soc., 2017, 139, 10204-10207.

DOI: 10.1021/jacs.7b05214

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In a radical-mediated strategy for β C-H amination of alcohols, imidates as radical relay chaperones serve as traceless directors that facilitates selective C-H functionalization via 1,5-hydrogen atom transfer (HAT) and enable net incorporation of ammonia at the β carbon. 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).

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Key Words

β-amino alcohols, iodosobenzene diacetate, photochemistry

ID: J48-Y2017