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

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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