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Radical Addition Enables 1,2‐Aryl Migration from a Vinyl‐Substituted All‐Carbon Quaternary Center
Author(s) -
Li Zexian,
Wang Minyan,
Shi Zhuangzhi
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202010839
Subject(s) - alkene , aryl , alkyl , chemistry , substituent , vicinal , photochemistry , organic chemistry , catalysis
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 a C‐radical bearing two electron‐withdrawing groups that is further reduced by a hydrogen donor to complete the domino sequence.