1351669-69-6Relevant articles and documents
Nickel-catalyzed cross-coupling of functionalized difluoromethyl bromides and chlorides with aryl boronic acids: A general method for difluoroalkylated arenes
Xiao, Yu-Lan,Guo, Wen-Hao,He, Guo-Zhen,Pan, Qiang,Zhang, Xingang
, p. 9909 - 9913,5 (2014)
Transition-metal-catalyzed difluoroalkylation of aromatics remains challenging despite the importance of difluoroalkylated arenes in medicinal chemistry. Herein, the first successful example of nickel-catalyzed difluoroalkylation of aryl boronic acids is described. The reaction allows access to a variety of functionalized difluoromethyl bromides and chlorides, and paves the way to highly cost-efficient synthesis of a wide range of difluoroalkylated arenes. The notable features of this protocol are its high generality, excellent functional-group compatibility, low-cost nickel-catalyst, and practicality for gram-scale production, thus providing a facile method for applications in drug discovery and development.
Enhancement of neighbouring-group participation in Cu0-promoted cross-coupling gem-difluoromethylenation of aryl/alkenyl halides with 1,3-azolic difluoromethyl bromides
Jiang, Haizhen,Lu, Wenjun,Yang, Kun,Ma, Guobin,Xu, Minjun,Li, Jian,Yao, Jianhua,Wan, Wen,Deng, Hongmei,Wu, Shaoxiong,Zhu, Shizheng,Hao, Jian
, p. 10084 - 10092 (2014/08/18)
A copper(0)-promoted direct reductive gem-difluoromethylenation of unactivated aryl or alkenyl halides with benzo-1,3-azolic (oxa-, thia- or aza-) difluoromethyl bromides or 2-bromodifluoromethyl-1,3-oxazoline has been developed for the construction of pharmaceutically important gem-difluoromethylene-linked twin molecules. The unique π-conjugated aryl-fused 1,3-azolic moiety in difluoromethyl bromide substrates could stabilise the reaction intermediates, which promotes the reactivities, providing facile access to the cross-coupling products in good to excellent yields, and allowing significant functional group tolerance. The reaction exhibits an enhanced neighbouring-group-participation effect. This method could provide a new strategy for the construction of gem-difluoromethylene-linked identical or nonidentical twin drugs through further functionalisation of 1,3-azolic skeletons.
Highly effective copper-mediated gem-difluoromethylenation of arylboronic acids
Ma, Guobin,Wan, Wen,Hu, Qingyang,Jiang, Haizhen,Wang, Jing,Zhu, Shizheng,Hao, Jian
supporting information, p. 7527 - 7530 (2014/07/07)
A copper-mediated gem-difluoromethylenation of aryl, heteroaryl and vinyl boronic acids with bromodifluoromethylated oxazole or thiazole derivatives has been developed. This novel reaction showed an excellent functional group tolerance and wide substrate scope, providing facile access to practical application in drug discovery and development. the Partner Organisations 2014.
Heteroaryldifluoromethylation of organoborons catalyzed by palladium: Facile access to aryl(heteroaryl)difluoromethanes
Xiao, Yu-Lan,Zhang, Bo,Feng, Zhang,Zhang, Xingang
supporting information, p. 4822 - 4825 (2015/04/27)
A first example of Pd-catalyzed heteroaryldifluoromethylation of organoborons with bromodifluoromethylated heteroarenes has been described. The use of phosphine ligand PAd2(n-Bu)·HI is critical for the reaction efficiency. With use of this ligand, a wide range of aryl(heteroaryl)-difluoromethanes were obtained with high efficiency. The notable features of this reaction are its broad substrate scope and excellent functional group compatibility, thus providing a facile protocol for application in drug discovery and development.
