1537172-08-9Relevant academic research and scientific papers
Highly γ-Selective Arylation and Carbonylative Arylation of 3-Bromo-3,3-difluoropropene via Nickel Catalysis
Cheng, Ran,Sang, Yueqian,Gao, Xing,Zhang, Shu,Xue, Xiao-Song,Zhang, Xingang
supporting information, p. 12386 - 12391 (2021/05/03)
A nickel-catalyzed highly γ-regioselective arylation and carbonylative arylation of 3-bromo-3,3-difluoropropene has been developed. The reaction proceeds under mild reaction conditions, providing the gem-difluoroalkenes with high efficiency and good functional group tolerance. The resulting gem-difluoroalkenes can serve as versatile building blocks for diversified synthesis. Preliminary mechanistic studies and density functional theory calculations reveal that both non-radical and radical pathways are possible for the reaction, and the radical pathway is more likely. The high γ-regioselectivity results from the β-bromide elimination of alkylnickel(II) species or from the reductive elimination of nickel(III) species [(aryl)(CF2=CHCH2)NiIII(Ln)X]. The γ-selective carbonylation of 3-bromo-3,3-difluoropropene under 1 atm CO gas also provides a new way for nickel-catalyzed carbonylation.
Highly selective gem -difluoroallylation of organoborons with bromodifluoromethylated alkenes catalyzed by palladium
Min, Qiao-Qiao,Yin, Zengsheng,Feng, Zhang,Guo, Wen-Hao,Zhang, Xingang
supporting information, p. 1230 - 1233 (2014/02/14)
A first example of Pd-catalyzed gem-difluoroallylation of organoborons using 3-bromo-3,3-difluoropropene (BDFP) in high efficiency with high α/γ-substitution regioselectivity has been developed. The reaction can also be extended to substituted BDFPs and has advantages of low catalyst loading (0.8 to 0.01 mol %), broad substrate scope, and excellent functional group compatibility, thus providing a facile route for practical application in drug discovery and development.
