52707-92-3Relevant articles and documents
A Straightforward Conversion of Activated Amides and Haloalkanes into Esters under Transition-Metal-Free Cs 2 CO 3 /DMAP Conditions
Chen, Liuqing,Gu, Ying,Jian, Junsheng,Liu, Yueping,Miao, Liqiong,Wang, Zijia,Zeng, Zhuo
, p. 4078 - 4084 (2019)
The esterification of activated amides, N -acylsaccharins, under transition-metal-free conditions with good functional group tolerance has been developed, resulting in C-N cleavage leading to efficient synthesis of a variety of esters in moderate to good yields. This work demonstrates that esterification may proceed by using simple N -acylsaccharins, haloalkanes, and Cs 2 CO 3 as oxygen source.
Palladium-catalyzed decarbonylative suzuki-miyaura coupling of amides to achieve biaryls via C-N bond cleavage
Luo, Zhongfeng,Xiong, Li,Liu, Tingting,Zhang, Yuqi,Lu, Siqi,Chen, Yuwen,Guo, Weijie,Zhu, Yulin,Zeng, Zhuo
, p. 10559 - 10568 (2019/09/30)
The palladium-catalyzed decarbonylative Suzuki-Miyaura coupling of amides via selective amide C-N bond cleavage was reported, which afforded mild access to substitute biaryl products in the presence of low catalyst loading with NaHCO3 as the base in good yields within 4 h (29 examples).
N-acylsaccharins: Stable electrophilic amide-based acyl transfer reagents in Pd-catalyzed Suzuki-Miyaura coupling via N-C cleavage
Liu, Chengwei,Meng, Guangrong,Liu, Yongmei,Liu, Ruzhang,Lalancette, Roger,Szostak, Roman,Szostak, Michal
supporting information, p. 4194 - 4197 (2016/09/09)
The development of efficient catalytic methods for N-C bond cleavage in amides remains an important synthetic challenge. The first Pd-catalyzed Suzuki-Miyaura cross-coupling of N-acylsaccharins with boronic acids by selective N-C bond activation is reported. The reaction enables preparation of a variety of functionalized diaryl and alkyl-aryl ketones with broad functional group tolerance and in good to excellent yields. Of general interest, N-acylsaccharins serve as new, highly reactive, bench-stable, economical, amide-based, electrophilic acyl transfer reagents via acyl-metal intermediates. Mechanistic studies strongly support the amide N-C(O) bond twist as the enabling feature of N-acylsaccharins in the N-C bond cleavage.
