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Visible Light Accelerated Vinyl C–H Arylation in Pd‐Catalysis: Application in the Synthesis of ortho Tetra‐substituted Vinylarene Atropisomers
Author(s) -
Feng Jia,
Li Bin,
Jiang Julong,
Zhang Mingkai,
Ouyang Wenbai,
Li Chunyu,
Fu Yao,
Gu Zhenhua
Publication year - 2018
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201700618
Subject(s) - chemistry , atropisomer , tetra , visible spectrum , surface modification , catalysis , photochemistry , photosensitizer , palladium , irradiation , polymer chemistry , medicinal chemistry , organic chemistry , physics , optoelectronics , nuclear physics
A visible light accelerated C–H functionalization reaction in palladium‐catalyzed arylation of vinyl arenes with diaryliodonium salts is reported in the absence of additional photosensitizer. The kinetic isotope effect ( k H / k D ) was changed from 3.6 (under darkness) to 1.1 when irradiated by visible light, which indicated that the C–H functionalization step was the rate determining step under darkness and significantly accelerated by the irradiation of visible light. Finally the synthesis of ortho tetra‐substituted vinylarene atropisomers with high enantiospecificity was realized via this protocol.