19341-03-8Relevant articles and documents
Photoinduced Carbamoylation of C(sp3)H Bonds with Isocyanates
Ishida, Naoki,Kawasaki, Tairin,Murakami, Masahiro,Tomono, Ryota,Yamazaki, Katsushi
supporting information, p. 1684 - 1684 (2021/09/16)
Alkylbenzenes coupled with isocyanates at the benzylic position upon irradiation with visible light in the presence of an iridium photoredox catalyst, a bromide anion, and a nickel catalyst, producing N-substituted α-aryl amides. An analogous carbamoylation reaction of aliphatic CH bonds of alkanes took place when UV light and a diaryl ketone were used instead of visible light and the iridium complex. The present reaction offers a straightforward and atom-economical method for the synthesis of carboxamides starting from hydrocarbons with one-carbon extension.
Asymmetric Markovnikov Hydroaminocarbonylation of Alkenes Enabled by Palladium-Monodentate Phosphoramidite Catalysis
Yao, Ya-Hong,Yang, Hui-Yi,Chen, Ming,Wu, Fei,Xu, Xing-Xing,Guan, Zheng-Hui
supporting information, p. 85 - 91 (2021/01/12)
A palladium-catalyzed asymmetric Markovnikov hydroaminocarbonylation of alkenes with anilines has been developed for the atom-economical synthesis of 2-substituted propanamides bearing an α-stereocenter. A novel phosphoramidite ligand L16 was discovered which exhibited very high reactivity and selectivity in the reaction. This asymmetric Markovnikov hydroaminocarbonylation employs readily available starting materials and tolerates a wide range of functional groups, thus providing a facile and straightforward method for the regio- and enantioselective synthesis of 2-substituted propanamides under ambient conditions. Mechanistic studies revealed that the reaction proceeds through a palladium hydride pathway.
Nickel (II)-Catalyzed efficient aminocarbonylation of unreactive alkanes with formanilides—Exploiting the deformylation behavior of imides
Han, Zhang,Chaowei, Dai,Lice, Liu,Hongfei, Ma,Hongzhong, Bu,Yufeng, Li
, p. 3712 - 3718 (2018/05/29)
Challenging functionalization of C(sp3)-H has recently attracted much attention of organic chemists. In this paper, we developed a Ni(acac)2-catalyzed activation of unreactive alkanes with formanilides in the presence of carbon monoxide to furnish moderate to excellent yields of amides. This is the first example of aminocarbonylation of inert alkanes using nickel-based catalyst, and formanilides is disclosed to be an interesting amine source owing to the peculiar deformylation nature of imide intermediates.