99421-73-5Relevant academic research and scientific papers
Merging Photochemistry with Electrochemistry: Functional-Group Tolerant Electrochemical Amination of C(sp3)?H Bonds
Wang, Fei,Stahl, Shannon S.
supporting information, p. 6385 - 6390 (2019/03/21)
Direct amination of C(sp3)?H bonds is of broad interest in the realm of C?H functionalization because of the prevalence of nitrogen heterocycles and amines in pharmaceuticals and natural products. Reported here is a combined electrochemical/pho
Directed β C-H Amination of Alcohols via Radical Relay Chaperones
Wappes, Ethan A.,Nakafuku, Kohki M.,Nagib, David A.
supporting information, p. 10204 - 10207 (2017/08/10)
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.
