Highly enantioselective intermolecular carbene insertion to C–H and Si–H bonds catalyzed by a chiral iridium(III) complex of a D4-symmetric Halterman porphyrin ligand

Jing-Cui Wang; Zhen-Jiang Xu; Zhen Guo; Qing-Hai Deng; Cong-Ying Zhou; Xiao-Long Wan; Chi-Ming Che

doi:10.1039/C2CC30441D

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Highly enantioselective intermolecular carbene insertion to C–H and Si–H bonds catalyzed by a chiral iridium(iii) complex of a D₄-symmetric Halterman porphyrin ligand†‡

Jing-Cui Wang,^a Zhen-Jiang Xu,^a Zhen Guo,^b Qing-Hai Deng,^a Cong-Ying Zhou,^b Xiao-Long Wan^a and Chi-Ming Che*^ab

Author affiliations

* Corresponding authors

^a Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, 354 Feng Lin Road, Shanghai, China

^b Department of Chemistry, State Key Laboratory of Synthetic Chemistry, and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong, China
E-mail: cmche@hku.hk
Fax: +852 2857-1586
Tel: +8522859-2154

Abstract

The chiral iridium porphyrin [Ir((−)-D₄-Por*)(Me)(EtOH)] displays excellent reactivity and stereoselectivity towards carbene insertion to C–H and Si–H bonds, affording corresponding products in high yields (up to 96%) and high enantioselectivities (up to 98% ee).

This article is part of the themed collection: Porphyrins & Phthalocyanines

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Article information

DOI: https://doi.org/10.1039/C2CC30441D
Article type: Communication
Submitted: 19 Jan 2012
Accepted: 09 Mar 2012
First published: 26 Mar 2012

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Chem. Commun., 2012,48, 4299-4301

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Highly enantioselective intermolecular carbene insertion to C–H and Si–H bonds catalyzed by a chiral iridium(III) complex of a D₄-symmetric Halterman porphyrin ligand

J. Wang, Z. Xu, Z. Guo, Q. Deng, C. Zhou, X. Wan and C. Che, Chem. Commun., 2012, 48, 4299 DOI: 10.1039/C2CC30441D

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Chemical Communications