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

J Am Chem Soc. 2017 Sep 27;139(38):13554-13561. doi: 10.1021/jacs.7b07368. Epub 2017 Sep 14.

Authors

Kenan Tokmic¹, Bailey J Jackson¹, Andrea Salazar¹, Toby J Woods¹, Alison R Fout¹

Affiliation

¹ School of Chemical Sciences, University of Illinois at Urbana-Champaign , 600 S. Mathews Avenue, Urbana, Illinois 61801, United States.

PMID: 28906106
DOI: 10.1021/jacs.7b07368

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.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Research Support, Non-U.S. Gov't