63633-75-0Relevant academic research and scientific papers
Palladium-catalyzed Sonogashira coupling of amides: Access to ynones: Via C-N bond cleavage
Cui, Ming,Wu, Hongxiang,Jian, Junsheng,Wang, Hui,Liu, Chao,Daniel, Stelck,Zeng, Zhuo
, p. 12076 - 12079 (2016)
The first palladium-catalyzed Sonogashira coupling of amides has been developed, which proceeds via a selective cleavage of the N-acylsaccharin C-N bond. Notably, the new approach employs N-acylsaccharins as coupling partners to give ynones in good to excellent yield. This protocol can be efficiently utilized in the synthesis of a broad array of ynones under low catalyst loading and Cu-free conditions.
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
supporting information, p. 4078 - 4084 (2019/10/28)
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).
Rhodium-catalyzed C-H functionalization with N-acylsaccharins
Wu, Hongxiang,Liu, Tingting,Cui, Ming,Li, Yue,Jian, Junsheng,Wang, Hui,Zeng, Zhuo
supporting information, p. 536 - 540 (2017/01/25)
A rhodium-catalyzed C-H functionalization with activated amides by decarbonylation has been developed. Notably, this is the first C-H arylation employing N-acylsaccharins as coupling partners to give biaryls in good to excellent yields. The highlight of the work is the high tolerance of functional groups such as formyl, ester, and vinyl and the use of a removable directing group.
Suzuki Coupling of Amides via Palladium-Catalyzed C–N Cleavage of N-Acylsaccharins
Wu, Hongxiang,Li, Yue,Cui, Ming,Jian, Junsheng,Zeng, Zhuo
supporting information, p. 3876 - 3880 (2016/12/16)
A palladium-catalyzed cross-coupling of activated amides with arylboronic acids has been developed via C–N bond cleavage. This approach demonstrated high tolerance to a variety of alkyl, aryl, heterocyclic and vinyl substituents. Unsymmetrical ketones could be achieved in excellent yield under mild conditions with 1% catalyst loadings. (Figure presented.).
