1534433-39-0Relevant articles and documents
Unprecedented copper-mediated oxidative demethylation of propionamides via bidentate-chelation assistance
Liu, Jing-Hui,Cui, Mian,Lu, Xiao-Yu,Zhang, Zhen-Qi,Xiao, Bin,Fu, Yao
, p. 1242 - 1245 (2016/01/15)
A copper-mediated directed demethylation of propionamides has been developed. This reaction proceeds predominantly at the α-methyl groups of aliphatic amides with high efficiency and provides a unique tool for the direct cleavage of unactivated C(sp3)-C(sp3) bonds. The directing groups can be smoothly removed to afford the corresponding alkyl carboxylic acids.
Nickel-catalyzed direct arylation of C(sp3)-H bonds in aliphatic amides via bidentate-chelation assistance
Aihara, Yoshinori,Chatani, Naoto
supporting information, p. 898 - 901 (2014/02/14)
The Ni-catalyzed, direct arylation of C(sp3)-H (methyl and methylene) bonds in aliphatic amides containing an 8-aminoquinoline moiety as a bidentate directing group with aryl halides is described. Deuterium-labeling experiments indicate that the C-H bond cleavage step is fast and reversible. Various nickel complexes including both Ni(II) and Ni(0) show a high catalytic activity. The results of a series of mechanistic experiments indicate that the catalytic reaction does not proceed through a Ni(0)/Ni(II) catalytic cycle, but probably through a Ni(II)/Ni(IV) catalytic cycle.
