B–N/B–H Transborylation: borane-catalysed nitrile hydroboration

The reduction of nitriles to primary amines is a useful transformation in organic synthesis, however, it often relies upon stoichiometric reagents or transition-metal catalysis. Herein, a borane-catalysed hydroboration of nitriles to give primary amines is reported. Good yields (48–95%) and chemosel...

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Autores principales: Meger, Filip, Kwok, Alexander C W, Gilch, Franziska, Willcox, Dominic R, Hendy, Alex J, Nicholson, Kieran, Bage, Andrew D, Langer, Thomas, Hunt, Thomas A, Thomas, Stephen P
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9531558/
https://www.ncbi.nlm.nih.gov/pubmed/36247978
http://dx.doi.org/10.3762/bjoc.18.138
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author Meger, Filip
Kwok, Alexander C W
Gilch, Franziska
Willcox, Dominic R
Hendy, Alex J
Nicholson, Kieran
Bage, Andrew D
Langer, Thomas
Hunt, Thomas A
Thomas, Stephen P
author_facet Meger, Filip
Kwok, Alexander C W
Gilch, Franziska
Willcox, Dominic R
Hendy, Alex J
Nicholson, Kieran
Bage, Andrew D
Langer, Thomas
Hunt, Thomas A
Thomas, Stephen P
author_sort Meger, Filip
collection PubMed
description The reduction of nitriles to primary amines is a useful transformation in organic synthesis, however, it often relies upon stoichiometric reagents or transition-metal catalysis. Herein, a borane-catalysed hydroboration of nitriles to give primary amines is reported. Good yields (48–95%) and chemoselectivity (e.g., ester, nitro, sulfone) were observed. DFT calculations and mechanistic studies support the proposal of a double B–N/B–H transborylation mechanism.
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spelling pubmed-95315582022-10-14 B–N/B–H Transborylation: borane-catalysed nitrile hydroboration Meger, Filip Kwok, Alexander C W Gilch, Franziska Willcox, Dominic R Hendy, Alex J Nicholson, Kieran Bage, Andrew D Langer, Thomas Hunt, Thomas A Thomas, Stephen P Beilstein J Org Chem Letter The reduction of nitriles to primary amines is a useful transformation in organic synthesis, however, it often relies upon stoichiometric reagents or transition-metal catalysis. Herein, a borane-catalysed hydroboration of nitriles to give primary amines is reported. Good yields (48–95%) and chemoselectivity (e.g., ester, nitro, sulfone) were observed. DFT calculations and mechanistic studies support the proposal of a double B–N/B–H transborylation mechanism. Beilstein-Institut 2022-09-26 /pmc/articles/PMC9531558/ /pubmed/36247978 http://dx.doi.org/10.3762/bjoc.18.138 Text en Copyright © 2022, Meger et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Letter
Meger, Filip
Kwok, Alexander C W
Gilch, Franziska
Willcox, Dominic R
Hendy, Alex J
Nicholson, Kieran
Bage, Andrew D
Langer, Thomas
Hunt, Thomas A
Thomas, Stephen P
B–N/B–H Transborylation: borane-catalysed nitrile hydroboration
title B–N/B–H Transborylation: borane-catalysed nitrile hydroboration
title_full B–N/B–H Transborylation: borane-catalysed nitrile hydroboration
title_fullStr B–N/B–H Transborylation: borane-catalysed nitrile hydroboration
title_full_unstemmed B–N/B–H Transborylation: borane-catalysed nitrile hydroboration
title_short B–N/B–H Transborylation: borane-catalysed nitrile hydroboration
title_sort b–n/b–h transborylation: borane-catalysed nitrile hydroboration
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9531558/
https://www.ncbi.nlm.nih.gov/pubmed/36247978
http://dx.doi.org/10.3762/bjoc.18.138
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