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Radical Addition Enables 1,2-Aryl Migration from Vinyl-Substituted All-Carbon Quaternary Center
Release time:2020-09-24    clicks:1845

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.