185322-10-5Relevant academic research and scientific papers
Asymmetric Propargylic Radical Cyanation Enabled by Dual Organophotoredox and Copper Catalysis
Lu, Fu-Dong,Liu, Dan,Zhu, Lei,Lu, Liang-Qiu,Yang, Qian,Zhou, Quan-Quan,Wei, Yi,Lan, Yu,Xiao, Wen-Jing
supporting information, p. 6167 - 6172 (2019/04/17)
The first asymmetric propargylic radical cyanation was realized through a dual photoredox and copper catalysis. An organic photocatalyst serves to both generate propargyl radicals and oxidize Cu(I) species to Cu(II) species. A chiral Cu complex functions as an efficient organometallic catalyst to resemble the propargyl radical and cyanide in an enantio-controlled manner. Thus, a diverse range of optically active propargyl cyanides were produced with high reaction efficiency and enantioselectivities (28 examples, 57-97% yields and 83-98% ee). Moreover, mechanistic investigations including experiments and density functional theory calculations were performed to illustrate on the reaction pathway and stereochemical results.
Nickel-catalyzed asymmetric cross-couplings of racemic propargylic halides with arylzinc reagents
Smith, Sean W.,Fu, Gregory C.
supporting information; experimental part, p. 12645 - 12647 (2009/05/09)
A stereoconvergent method for the catalytic asymmetric Negishi cross-coupling of racemic secondary propargylic halides with arylzinc reagents has been developed. Neither family of compounds has previously been shown to be a suitable partner in such coupling processes. From a practical point of view, it is noteworthy that the catalyst components (NiCl2·glyme and pybox ligand 1) are commercially available. Copyright
