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

This account summarizes our recent work on metal-quinoid carbene (QC) chemistry including (a) dirhodium-catalyzed QC C(sp(2))-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(sp(3))-H insertion reaction initiated by an O-centered hydrogen-atom transfer reactivity of metal-QC species. Introduction Catalytic Quinoid Carbene Insertions into C(sp(2))-H Bonds Enabled by Carbene-Transfer Reactivity Ruthenium(II) Porphyrin Quinoid Carbene Complexes and Dual Reactivity Catalytic Quinoid Carbene Insertions into C(sp(3))-H Bonds Enabled by Hydrogen-Atom-Transfer Reactivity Perspective and Outlook

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This paper summarizes recent research on metal-quinoid carbene chemistry, focusing on dirhodium-catalyzed C(sp(2))-H insertion reactions, isolation and characterization of Ruthenium(II) porphyrin QC complexes, and iridium(III) porphyrin-catalyzed C(sp(3))-H insertion reactions.