Enantioselective Copper-Catalyzed Intermolecular Cyanobenzoyldifluoromethylation of Alkenes: Access to Chiral β-Difluoroacyl Nitriles

Autor: Fang, Mougui, Wu, Pingjie, Wang, Xia, Xie, Ziyue, Hou, Yali, Liu, Yao, Wu, Jingjing, Wu, Fanhong
Zdroj: The Journal of Organic Chemistry; March 2022, Vol. 87 Issue: 6 p4107-4111, 5p
Abstrakt: A novel asymmetric copper-catalyzed intermolecular cyanobenzoyldifluoromethylation of alkenes with iododifluoromethyl ketones and TMSCN has been reported, which provides a particularly valuable route to access chiral β-difluoroacyl nitriles with excellent enantioselectivities. The method permits the efficient cyanation of varied β-difluoroacyl-benzylic radicals in mild conditions with high functional group tolerance. The reaction proceeds through a radical pathway. In order to get insight into the stereochemical outcome, computational mechanistic studies were conducted.
Databáze: Supplemental Index