Olefin motifs permit facile, rapid diversification on complex molecular scaffolds. Although alkenes serve as a privileged functional handle, late-stage distal desaturation remains a synthetic challenge. Utilizing a cobalt-catalyzed chaperone activation strategy, a method to permit carbon-to-carbon alkene transfer was achieved. Through this approach, desaturation of a broad scope of amine precursors affords a range of distal desaturated natural and medicinally relevant products. Support for the proposed carbon-to-carbon hydrogen atom transfer mechanism includes DFT modeling of the reaction coordinate.

Transfer dehydrogenation via carbon-to-carbon HAT

ACS Spring 2022

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