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Merger of Visible Light Induced Oxidation and Enantioselective Alkylation with a Chiral Iridium Catalyst
Author(s) -
Wang Chuanyong,
Zheng Yu,
Huo Haohua,
Röse Philipp,
Zhang Lilu,
Harms Klaus,
Hilt Gerhard,
Meggers Eric
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201500998
Subject(s) - iridium , enantioselective synthesis , alkylation , enantiomer , photoredox catalysis , chemistry , catalysis , chirality (physics) , methylamines , photochemistry , enantiomeric excess , combinatorial chemistry , organic chemistry , photocatalysis , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark
A single chiral octahedral iridium(III) complex is used for visible light activated asymmetric photoredox catalysis. In the presence of a conventional household lamp and under an atmosphere of air, the oxidative coupling of 2‐acyl‐1‐phenylimidazoles with N , N ‐diaryl‐ N ‐(trimethylsilyl)methylamines provides aminoalkylated products in 61–93 % yields with high enantiomeric excess (90–98 % ee ). Notably, the iridium center simultaneously serves three distinct functions: as the exclusive source of chirality, as the catalytically active Lewis acid, and as a central part of the photoredox sensitizer. This conceptionally simple reaction Scheme may provide new avenues for the green synthesis of non‐racemic chiral molecules.