908520-36-5Relevant articles and documents
Bridging C?H Activation: Mild and Versatile Cleavage of the 8-Aminoquinoline Directing Group
Berger, Martin,Chauhan, Rajan,Rodrigues, Catarina A. B.,Maulide, Nuno
, p. 16805 - 16808 (2016)
8-Aminoquinoline has emerged as one of the most powerful bidentate directing groups in history of C?H activation within the last decade. However, cleavage of its robust amide bond has shown to be challenging in several cases, thus jeopardizing the general synthetic utility of the method. To overcome this limitation, we herein report a simple oxidative deprotection protocol. This transformation rapidly converts the robust amide to a labile imide, allowing subsequent cleavage in a simple one-pot fashion to rapidly access carboxylic acids or amides as final products.
Nickel-catalyzed direct arylation of C(sp3)-H bonds in aliphatic amides via bidentate-chelation assistance
Aihara, Yoshinori,Chatani, Naoto
, 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.
