Radical Addition Enables 1,2-Aryl Migration from Vinyl-Substituted All-Carbon Quaternary Center
Release time:2020-09-24 clicks:4231
The group publishes a Radical Addition Enables 1,2-Aryl Migration from Vinyl-Substituted All-Carbon Quaternary Center on Angew. Congrats Li !
ABSTRACT: An efficient method for photocatalytic perfluoroalkylation of vinyl-substituted all-carbon quaternary centers involving 1,2-aryl migration has been developed. The rearrangement reactions use fac-Ir(ppy)3 , visible light and commercially available fluoroalkyl halides and can generate valuable multisubstituted perfluoroalkylated compounds in a single step that would be challenging to prepare by other methods. Mechanistically, the photoinduced alkyl radical addition to an alkene leads to the migration of a vicinal aryl substituent from its adjacent all-carbon quaternary center with the concomitant generation of C-radical bearing two electron-withdrawing groups that is further reduced by a hydrogen donor to complete the domino sequence.