58734-19-3Relevant articles and documents
Ruthenium-Catalyzed Synthesis of Isoindolinones via Amide-Directed Addition of Aromatic C-H Bonds to Aldimines
Miura, Hiroki,Kimura, Yuriko,Terajima, Sachie,Shishido, Tetsuya
supporting information, p. 2807 - 2811 (2019/02/01)
Ruthenium-catalyzed addition of aromatic C-H bonds to aldimines is described. [RuCl2(p-cymene)]2 functions as an efficient catalyst to promote the coupling of aryl amides with aldimines in the presence of a catalytic amount of base to give the corresponding isoindolinone derivatives. The nature of the substituent at the N-atom of the amides is crucial for the efficient conversion of the substrates, and a p-toluenesulfonyl group is the functionality of choice. A variety of amides and aldimines participated in the present Ru-catalyzed reaction to furnish the corresponding isoindolinones in moderate to high yield.
Organocatalytic Direct N-Acylation of Amides with Aldehydes under Oxidative Conditions
Zheng, Chenguang,Liu, Xiang,Ma, Cheng
, p. 6940 - 6945 (2017/07/13)
The direct oxidative N-acylation reaction of primary amides with aryl/α,β-unsaturated aldehydes was achieved in the presence of azolium salt C3 and an inorganic base using 3,3′,5,5′-tetra-tert-butyldiphenoquinone as the oxidant, thus providing an efficient approach for the synthesis of three types of imide compounds including N-sulfonylcarboxamides, N-sulfinylcarboxamides, and dicarboxyimides in good yield.
Room-temperature ortho-alkoxylation and -halogenation of N-tosylbenzamides by using palladium(II)-catalyzed C-H activation
Peron, Florent,Fossey, Christine,Sopkova-Deoliveirasantos, Jana,Cailly, Thomas,Fabis, Frederic
supporting information, p. 7507 - 7513 (2014/06/23)
The N-tosylcarboxamide group can direct the room-temperature palladium-catalyzed C-H alkoxylation and halogenation of substituted arenes in a simple and mild procedure. The room-temperature stoichiometric cyclopalladation of N-tosylbenzamide was first studied, and the ability of the palladacycle to react with oxidants to form C-X and C-O bonds under mild conditions was demonstrated. The reaction conditions were then adapted to promote room-temperature ortho-alkoxylations and ortho-halogenations of N-tosylbenzamides using palladium as catalyst. The scope and limitation of both alkoxylations and halogenations was studied and the subsequent functional transformation of the N-tosylcarboxamide group through nucleophilic additions was evaluated. This methodology offers a simple and mild route to diversely functionalized arenes.
N-tosylcarboxamide as a transformable directing group for Pd-catalyzed C-H ortho-arylation
Peron, Florent,Fossey, Christine,Cailly, Thomas,Fabis, Frederic
supporting information; experimental part, p. 1827 - 1829 (2012/06/29)
The N-tosylcarboxamide group offers the possibility of directing the Pd-catalyzed C-H arylation of arenes providing a new entry to biarylcarboxamides. Moreover, its ability to react according to different reaction conditions including intramolecular reactions makes it a pivotal directing group for a divergent synthesis of biaryl-based compounds.
Iron-catalyzed nitrene insertion reaction for facile construction of amide compounds
Chen, Guo-Qiang,Xu, Zhen-Jiang,Liu, Yungen,Zhou, Cong-Ying,Che, Chi-Ming
scheme or table, p. 1174 - 1178 (2011/06/24)
A facile method for the construction of amide compounds from aldehydes by an iron-catalyzed nitrene insertion reaction has been developed. Both aryl and aliphatic aldehydes can directly afford the corresponding amides with an iron(II)-terpyridine (tpy) complex formed in situ as catalyst, and PhI=NTs as nitrogen source under mild reaction conditions. An ESI-MS study revealed the formation of [Fe(tpy)NTs)]+ as a reaction intermediate. Georg Thieme Verlag Stuttgart - New York.
