59960-39-3Relevant academic research and scientific papers
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.
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.
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.
Acid-free regioselective aminocarbonylation of alkenes
Liu, Huizhen,Yan, Ning,Dyson, Paul J.
supporting information, p. 7848 - 7851 (2014/07/08)
An efficient method for the synthesis of N-aryl monosubstituted carboxamides via the Pd-catalyzed carbonylation of alkenes with CO and amines is described. Mechanistic insights for this highly selective reaction are provided. This journal is the Partner O
Copper(ii) chloride mediated (aza)oxindole synthesis by oxidative coupling of Csp2-H and Csp3-H centers: Substrate scope and DFT study
Dey, Chandan,Larionov, Evgeny,Kuendig, E. Peter
supporting information, p. 6734 - 6743 (2013/10/01)
A CuCl2 mediated direct intramolecular oxidative coupling of Csp2-H and Csp3-H centers gives access to 3,3-disubstituted oxindoles containing aromatic, heteroaromatic and alkyl substituents as well as a heteroatom at the quaternary center in good to excellent yields. The reaction is carried out in the presence of NaOtBu and CuCl2 in DMF at 110 °C. The key step of this reaction is the formation of an amidyl radical by one electron oxidation of amide enolate followed by an intramolecular radical cyclization reaction (homolytic aromatic substitution reaction). A detailed DFT study shows that the cyclization of the amidyl radical is the rate-limiting step in the oxindole synthesis, whereas the second single electron transfer (SET) becomes the rate-determining step in the aza-oxindole formation. Computational data are in agreement with the experimentally observed relative reactivity and regioselectivity.
Microwave assisted efficient aminocarbonylation of N-tosylhydrazones with molybdenum hexacarbonyl and amines
Rao, K. Penta,Basak, Ashok K.,Raju, Amancha,Patil, Vikas S.,Reddy, L. Krishnakanth
, p. 5510 - 5513 (2013/09/23)
An efficient aminocarbonylation of N-tosylhydrazones derived from aromatic aldehydes and ketones mediated by molybdenum hexacarbonyl is reported. This method is palladium-free and provides a rapid access to the α-aryl acetamides in moderate to good yields.
Palladium-catalyzed amidation-hydrolysis reaction of gem-dihaloolefins: Efficient synthesis of homologated carboxamides from ketones
Ye, Wenchao,Mo, Jun,Zhao, Tiankun,Xu, Bin
supporting information; experimental part, p. 3246 - 3248 (2009/12/01)
A simple and efficient palladium-catalyzed amidation-hydrolysis reaction has been developed to afford N-aryl monosubstituted carboxamides in good to excellent yields from easily accessible ketone-derived gem-dihaloolefins and aryl amines.
