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Wang C, Zheng Y, Huo H, et al. Merger of visible light induced oxidation and enantioselective alkylation with a chiral iridium catalyst. Chemistry. 2015;21(20):7355-9doi: 10.1002/chem.201500998.
Wang, C., Zheng, Y., Huo, H., Röse, P., Zhang, L., Harms, K., Hilt, G., & Meggers, E. (2015). Merger of visible light induced oxidation and enantioselective alkylation with a chiral iridium catalyst. Chemistry (Weinheim an der Bergstrasse, Germany), 21(20), 7355-9. https://doi.org/10.1002/chem.201500998
Wang, Chuanyong, et al. "Merger of visible light induced oxidation and enantioselective alkylation with a chiral iridium catalyst." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,20 (2015): 7355-9. doi: https://doi.org/10.1002/chem.201500998
Wang C, Zheng Y, Huo H, Röse P, Zhang L, Harms K, Hilt G, Meggers E. Merger of visible light induced oxidation and enantioselective alkylation with a chiral iridium catalyst. Chemistry. 2015 May 11;21(20):7355-9. doi: 10.1002/chem.201500998. Epub 2015 Apr 01. PMID: 25832794.
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Chemistry. 2015 May 11;21(20):7355-9. doi: 10.1002/chem.201500998. Epub 2015 Apr 01.

Merger of visible light induced oxidation and enantioselective alkylation with a chiral iridium catalyst.

Chemistry (Weinheim an der Bergstrasse, Germany)

Chuanyong Wang, Yu Zheng, Haohua Huo, Philipp Röse, Lilu Zhang, Klaus Harms, Gerhard Hilt, Eric Meggers

Affiliations

  1. Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße 4, 35043 Marburg (Germany).

PMID: 25832794 DOI: 10.1002/chem.201500998

Abstract

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.

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: asymmetric catalysis; iridium; metal-centered chirality; photoredox catalysis; visible light

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