Cobalt-Catalyzed and Lewis Acid-Assisted Nitrile Hydrogenation to Primary Amines: A Combined Effort

Kenan Tokmic; Bailey J. Jackson; Andrea Salazar; Toby J. Woods; Alison R. Fout

doi:10.1021/jacs.7b07368

Cobalt-Catalyzed and Lewis Acid-Assisted Nitrile Hydrogenation to Primary Amines: A Combined Effort

Kenan Tokmic, Bailey J. Jackson, Andrea Salazar, Toby J. Woods, Alison R. Fout

Chemistry

Research output: Contribution to journal › Article

Abstract

The selective hydrogenation of nitriles to primary amines using a bench-stable cobalt precatalyst under 4 atm of H₂ is reported herein. The catalyst precursor was reduced in situ using NaHBEt₃, and the resulting Lewis acid formed, BEt₃, was found to be integral to the observed catalysis. Mechanistic insights gleaned from para-hydrogen induced polarization (PHIP) transfer NMR studies revealed that the pairwise hydrogenation of nitriles proceeded through a Co(I/III) redox process.

Original language	English (US)
Pages (from-to)	13554-13561
Number of pages	8
Journal	Journal of the American Chemical Society
Volume	139
Issue number	38
DOIs	https://doi.org/10.1021/jacs.7b07368
State	Published - Jan 1 2017

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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Tokmic, K., Jackson, B. J., Salazar, A., Woods, T. J., & Fout, A. R. (2017). Cobalt-Catalyzed and Lewis Acid-Assisted Nitrile Hydrogenation to Primary Amines: A Combined Effort. Journal of the American Chemical Society, 139(38), 13554-13561. https://doi.org/10.1021/jacs.7b07368

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