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Significance Insertion of CO into metal-alkyl bonds is one of the most characteristic and useful reactions of transition metal complexes. It is the key C-C bond-forming step in numerous organic reactions, ranging from commodity scale to the synthesis of pharmaceutical compounds. Polar molecules can strongly promote CO insertions, and the mechanism of this effect has been the subject of speculation for over five decades, and yet no satisfactory explanation has previously been offered. Here, we report that the unprecedented role of the promoter molecule is to displace an agostic C-H bond of the initial product of (unassisted) alkyl-to-CO migration, through a process facilitated by hydrogen-bonding, thereby affording an intermediate acyl complex that is more easily trapped than the initially formed agostic complex.

Polar molecules catalyze CO insertion into metal-alkyl bonds through the displacement of an agostic C-H bond