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

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

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...

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Veröffentlicht in:Journal of the American Chemical Society 2017-09, Vol.139 (38), p.13554-13561
Hauptverfasser: Tokmic, Kenan, Jackson, Bailey J, Salazar, Andrea, Woods, Toby J, Fout, Alison R
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container_issue 38
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container_title Journal of the American Chemical Society
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creator Tokmic, Kenan
Jackson, Bailey J
Salazar, Andrea
Woods, Toby J
Fout, Alison R
description 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.
doi_str_mv 10.1021/jacs.7b07368
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title Cobalt-Catalyzed and Lewis Acid-Assisted Nitrile Hydrogenation to Primary Amines: A Combined Effort
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