Metal-Quinoid Carbene Chemistry: From Bonding to C–H Activation Catalysis

Hai-Xu Wang; Kai Wu; Chi-Ming Che

doi:10.1055/s-0040-1707221

Synlett, Table of Contents

Synlett 2021; 32(03): 249-257
DOI: 10.1055/s-0040-1707221

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Metal-Quinoid Carbene Chemistry: From Bonding to C–H Activation Catalysis

Hai-Xu Wang

^aState Key Laboratory of Synthetic Chemistry, Department of Chemistry, The University of Hong Kong, Pofkulam Road, Hong Kong, P. R. of China

,

Kai Wu

^aState Key Laboratory of Synthetic Chemistry, Department of Chemistry, The University of Hong Kong, Pofkulam Road, Hong Kong, P. R. of China

,

Chi-Ming Che∗

^aState Key Laboratory of Synthetic Chemistry, Department of Chemistry, The University of Hong Kong, Pofkulam Road, Hong Kong, P. R. of China

^bHKU Shenzhen Institute of Research & Innovation, Shenzhen, 518053, P. R. of China Email: cmche@hku.hk

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Abstract

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Abstract

This account summarizes our recent work on metal-quinoid carbene (QC) chemistry including (a) dirhodium-catalyzed QC C(sp²)–H insertion reactions enabled by a C-centered carbene-transfer reactivity, (b) the isolation, characterization, and dual reactivity of Ru(II) porphyrin QC complexes, and (c) iridium(III) porphyrin-catalyzed QC C(sp³)–H insertion reaction initiated by an O-centered hydrogen-atom transfer reactivity of metal–QC species.

1 Introduction

2 Catalytic Quinoid Carbene Insertions into C(sp²)–H Bonds Enabled by Carbene-Transfer Reactivity

3 Ruthenium(II) Porphyrin Quinoid Carbene Complexes and Dual Reactivity

4 Catalytic Quinoid Carbene Insertions into C(sp³)–H Bonds Enabled by Hydrogen-Atom-Transfer Reactivity

5 Perspective and Outlook

Key words

metal carbenes - homogeneous catalysis - C–H functionalization - arylation - quinoid carbenes - hydrogen-atom transfer

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References

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