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Photo‐Induced Chloride Atom Transfer Radical Addition and Aminocarbonylation Reactions
Author(s) -
Pan Hao,
Ge Huaqi,
He Rong,
Huang Weichao,
Wang Lele,
Wei Yingcong,
Sa Rongjian,
Wang YanJie,
Yuan Rusheng
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900252
Subject(s) - chemistry , radical , aryl , aryl radical , photochemistry , hydrogen atom abstraction , catalysis , chlorine , chlorine atom , yield (engineering) , carbon monoxide , hydrogen atom , reactive intermediate , chloride , organic chemistry , medicinal chemistry , group (periodic table) , alkyl , materials science , metallurgy
A photo‐induced atom transfer radical addition (ATRA) of aryl chlorides onto alkenes has been developed in the synthesis of chloroalkyl benzenes, in which chlorine radicals and aryl radicals can be generated simultaneously at ambient temperature without the involvement of any initiator or catalyst. The inherently reactive and energetic chlorine radicals also benefit a photo‐induced aminocarbonylation reaction of aryl chlorides with carbon monoxide and amines via a hydrogen‐abstraction step. These two reactions can provide an inspiration for organic reaction with a radical‐designed process. Finally, a photo‐induced multi‐phase reaction system is extended to flow mode to yield scaled‐up products on a gram scale.