Carbonyl addition is an important reaction in organic chemistry because of its usefulness in creating complexity from small molecules. The Krische group has developed transition metal catalyzed redox-triggered C-C couplings of alcohols <i>via</i> transfer hydrogenation, bypassing the need of stoichiometric (organo)metallic reagents. Combined redox events that make use of nucleophile-electrophile pairs for carbonyl addition are more efficient in terms of step- and atom economy. In ruthenium and osmium catalyzed C-C couplings, the LUMO-lowering effect of pyridines and esters, which is amplified by their capacity for chelation, was essential in promoting alkene-carbonyl oxidative coupling pathways. The putative metallacycle intermediate has been isolated and characterized, and reversible metallacycle formation has been demonstrated.

Transition metal catalyzed redox-triggered C-C couplings of alcohols <i>via</i> transfer hydrogenation

249th National Meeting (2015)

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Transition metal catalyzed redox-triggered C-C couplings of alcohols via transfer hydrogenation