Transfer hydrogenations eschew the use of molecular H<sub>2</sub> in the hydrogenation of unsaturated bonds in favor of hydrogen donors. Such hydrogen donors require activation in transfer hydrogenation processes and classically this has been achieved by catalysts featuring noble metals such as ruthenium, palladium or platinum. An upswell of recent reports show that such catalysis can be achieved in similar efficiencies and performance by base-metal catalysts featuring earth abundant metals such as manganese. Herein we report a novel Mn(I)-b-aminophosphine (Mn(I)-PN) complex that is capable of transfer hydrogenation, chemoselective transfer hydrogenation of chalcones, and allyl alcohol redox isomerization. The complex can be readily synthesized in 4 steps in high yields (59%) and gram quantities. Moreover, the Mn(I)-PN system demonstrates unique chemoselectivity in the transfer hydrogenation of chalcones compared to other bidentate Mn(I) complexes, showing a preference to generate a saturated ketone as the major product and a saturated alcohol as the minor product. The absence of an allyl alcohol product lead to the determination that the complex could isomerize allyl alcohols to saturated ketones in the absence of a hydrogen donor; showcasing a rare example of an Mn(I)-catalyzed redox isomerization of an allyl alcohol.

Mn(I)-PN catalyzed transfer hydrogenations and redox isomerizations of allyl alcohols

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.