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Asymmetric Radical–Radical Cross‐Coupling through Visible‐Light‐Activated Iridium Catalysis
Author(s) -
Wang Chuanyong,
Qin Jie,
Shen Xiaodong,
Riedel Radostan,
Harms Klaus,
Meggers Eric
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201509524
Subject(s) - chemistry , catalysis , iridium , photochemistry , photoredox catalysis , photocatalysis , catalytic cycle , trifluoromethyl , enantioselective synthesis , electron transfer , substrate (aquarium) , chiral lewis acid , photoinduced electron transfer , lewis acids and bases , organic chemistry , alkyl , oceanography , geology
Combining single electron transfer between a donor substrate and a catalyst‐activated acceptor substrate with a stereocontrolled radical–radical recombination enables the visible‐light‐driven catalytic enantio‐ and diastereoselective synthesis of 1,2‐amino alcohols from trifluoromethyl ketones and tertiary amines. With a chiral iridium complex acting as both a Lewis acid and a photoredox catalyst, enantioselectivities of up to 99 % ee were achieved. A quantum yield of <1 supports the proposed catalytic cycle in which at least one photon is needed for each asymmetric CC bond formation mediated by single electron transfer.