5 years ago

Cobalt-Catalyzed Stereoretentive Hydrogen Isotope Exchange of C(sp3)–H Bonds

Cobalt-Catalyzed Stereoretentive Hydrogen Isotope Exchange of C(sp3)–H Bonds
W. Neil Palmer, Paul J. Chirik
Cobalt dialkyl complexes bearing α-diimine ligands proved to be active precatalysts for the nondirected, C(sp3)–H selective hydrogen isotope exchange (HIE) of alkylarenes using D2 gas as the deuterium source. Alkylarenes with a variety of substitution patterns and heteroatom substituents on the arene ring were successfully labeled, enabling high levels of incorporation into primary, secondary, and tertiary benzylic C(sp3)–H bonds. In some cases, the HIE proceeded with high diastereoselectivity and application of the cobalt-catalyzed method to enantioenriched substrates with benzylic stereocenters provided enantioretentive hydrogen isotope exchange at tertiary carbons.

Publisher URL: http://dx.doi.org/10.1021/acscatal.7b02051

DOI: 10.1021/acscatal.7b02051

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