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

Authors :
Tokmic K
Jackson BJ
Salazar A
Woods TJ
Fout AR
Source :
Journal of the American Chemical Society [J Am Chem Soc] 2017 Sep 27; Vol. 139 (38), pp. 13554-13561. Date of Electronic Publication: 2017 Sep 14.
Publication Year :
2017

Abstract

The selective hydrogenation of nitriles to primary amines using a bench-stable cobalt precatalyst under 4 atm of H <subscript>2</subscript> is reported herein. The catalyst precursor was reduced in situ using NaHBEt <subscript>3</subscript> , and the resulting Lewis acid formed, BEt <subscript>3</subscript> , 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.

Details

Language :
English
ISSN :
1520-5126
Volume :
139
Issue :
38
Database :
MEDLINE
Journal :
Journal of the American Chemical Society
Publication Type :
Academic Journal
Accession number :
28906106
Full Text :
https://doi.org/10.1021/jacs.7b07368