Cobalt-catalyzed regioselective hydrohydrazination of epoxides?

Organic & Biomolecular Chemistry Pub Date: 2020-02-03 DOI: 10.1039/D0OB00037J

Abstract

Using an air-stable cobalt catalyst [Cp*Co(1,2-Ph2PC6H4S)(NCMe)]BF4 (1, Cp* = Me5C5?), we have achieved catalytic regioselective hydrohydrazination of epoxides to 1,1-hydrazinoalcohols in an atom-economical manner. The catalysis involves a cobalt–hydrazine intermediate, in which the NH2 group of the hydrazine binds to the metal center, inhibiting its nucleophilic reactivity and allowing the NH group to participate in the regioselective hydrohydrazination.

Graphical abstract: Cobalt-catalyzed regioselective hydrohydrazination of epoxides
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