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.
Copper-catalyzed transformation of alkyl nitriles to N -arylacetamide using diaryliodonium salts
Sallio, Romain,Payard, Pierre-Adrien,Pakulski, Pawe?,Diachenko, Iryna,Fabre, Indira,Berteina-Raboin, Sabine,Colas, Cyril,Ciofini, Ilaria,Grimaud, Laurence,Gillaizeau, Isabelle
, p. 15885 - 15889 (2021/05/19)
This work reports a simple and efficient method for the copper-catalyzed redox-neutral transformation of alkyl nitriles using eco-friendly diaryliodonium salts and leading to N-arylacetamides. The method features high efficiency, broad substrate scope and good functional group tolerance.
Intermediate formation enabled regioselective access to amide in the Pd-catalyzed reductive aminocarbonylation of olefin with nitroarene
Li, Fuwei,Shi, Lijun,Xia, Chungu,Yang, Li
, p. 1152 - 1160 (2020/03/13)
An efficient route for the palladium-catalyzed reductive aminocarbonylation of olefins with nitroarenes was developed using carbon monoxide (CO) as both reductant and carbonyl source, which enables facile access to amides with excellent regioselectivity a
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.
Palladium-Catalyzed Hydrocarbonylative C-N Coupling of Alkenes with Amides
Zhou, Xibing,Zhang, Guoying,Gao, Bao,Huang, Hanmin
supporting information, p. 2208 - 2212 (2018/04/30)
An efficient palladium-catalyzed hydrocarbonylative C-N coupling of alkenes with amides has been developed. The reaction was performed via hydrocarbonylation of alkenes, followed by acyl metathesis with amides. Both intermolecular and intramolecular react
Organic ligand-free carbonylation reactions with unsupported bulk Pd as catalyst
Liu, Shujuan,Wang, Hongli,Dai, Xingchao,Shi, Feng
supporting information, p. 3457 - 3462 (2018/08/06)
Herein, surprising results for bulk Pd-catalyzed carbonylation reactions are presented. Three types of carbonylation reactions can be realized efficiently under organic ligand-free conditions, namely, hydroaminocarbonylation of olefins, aminocarbonylation of aryl iodides and oxidative carbonylation of amines, which almost cover all the known mechanisms in carbonylation reactions. Notably, the bulk Pd catalyst system exhibited better catalytic activity than the classical homogeneous PdCl2/(2-OMePh)3P catalyst system. This study will create a momentous and new field of green carbonylation reactions.
Reaction of azides and enolisable aldehydes under the catalysis of organic bases and: Cinchona based quaternary ammonium salts
Destro, Dario,Sanchez, Sandra,Cortigiani, Mauro,Adamo, Mauro F. A.
, p. 5227 - 5235 (2017/07/11)
Herein we report a two-step sequence for the preparation of amides starting from azides and enolisable aldehydes. The reaction proceeded via the formation of triazoline intermediates that were converted into amides via Lewis acid catalysis. Preliminary st
Palladium-catalyzed highly regioselective hydroaminocarbonylation of aromatic alkenes to branched amides
Zhu, Jinping,Gao, Bao,Huang, Hanmin
supporting information, p. 2910 - 2913 (2017/04/11)
Pd(t-Bu3P)2 has been successfully identified as an efficient catalyst for the hydroaminocarbonylation of aromatic alkenes to branched amides under relatively mild reaction conditions. With hydroxylamine hydrochloride as an additive,
Visible Light-Induced Radical Rearrangement to Construct C-C Bonds via an Intramolecular Aryl Migration/Desulfonylation Process
Li, Yuyuan,Hu, Bei,Dong, Wuheng,Xie, Xiaomin,Wan, Jun,Zhang, Zhaoguo
, p. 7036 - 7041 (2016/08/30)
A highly efficient intramolecular selective aryl migration/desulfonylation of 2-bromo-N-aryl-N-(arenesulfonyl)amide via visible light-induced photoredox catalysis has been accomplished. This approach allows for the construction of a variety of multisubstituted N,2-diarylacetamide under mild reaction conditions.