Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)(3) and NaBH(4)

An operationally simple and environmentally benign formal hydrogenation protocol has been developed using highly abundant iron(iii) salts and an inexpensive, bench stable, stoichiometric reductant, NaBH(4), in ethanol, under ambient conditions. This reaction has been applied to the reduction of term...

Descripción completa

Detalles Bibliográficos
Autores principales: MacNair, Alistair J., Tran, Ming-Ming, Nelson, Jennifer E., Sloan, G. Usherwood, Ironmonger, Alan, Thomas, Stephen P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2014
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4295815/
https://www.ncbi.nlm.nih.gov/pubmed/24914735
http://dx.doi.org/10.1039/c4ob00945b
_version_ 1782352884500791296
author MacNair, Alistair J.
Tran, Ming-Ming
Nelson, Jennifer E.
Sloan, G. Usherwood
Ironmonger, Alan
Thomas, Stephen P.
author_facet MacNair, Alistair J.
Tran, Ming-Ming
Nelson, Jennifer E.
Sloan, G. Usherwood
Ironmonger, Alan
Thomas, Stephen P.
author_sort MacNair, Alistair J.
collection PubMed
description An operationally simple and environmentally benign formal hydrogenation protocol has been developed using highly abundant iron(iii) salts and an inexpensive, bench stable, stoichiometric reductant, NaBH(4), in ethanol, under ambient conditions. This reaction has been applied to the reduction of terminal alkenes (22 examples, up to 95% yield) and nitro-groups (26 examples, up to 95% yield). Deuterium labelling studies indicate that this reaction proceeds via an ionic rather than radical mechanism.
format Online
Article
Text
id pubmed-4295815
institution National Center for Biotechnology Information
language English
publishDate 2014
publisher Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-42958152015-01-26 Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)(3) and NaBH(4) MacNair, Alistair J. Tran, Ming-Ming Nelson, Jennifer E. Sloan, G. Usherwood Ironmonger, Alan Thomas, Stephen P. Org Biomol Chem Chemistry An operationally simple and environmentally benign formal hydrogenation protocol has been developed using highly abundant iron(iii) salts and an inexpensive, bench stable, stoichiometric reductant, NaBH(4), in ethanol, under ambient conditions. This reaction has been applied to the reduction of terminal alkenes (22 examples, up to 95% yield) and nitro-groups (26 examples, up to 95% yield). Deuterium labelling studies indicate that this reaction proceeds via an ionic rather than radical mechanism. Royal Society of Chemistry 2014-07-28 2014-06-10 /pmc/articles/PMC4295815/ /pubmed/24914735 http://dx.doi.org/10.1039/c4ob00945b Text en This journal is © The Royal Society of Chemistry 2014 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
MacNair, Alistair J.
Tran, Ming-Ming
Nelson, Jennifer E.
Sloan, G. Usherwood
Ironmonger, Alan
Thomas, Stephen P.
Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)(3) and NaBH(4)
title Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)(3) and NaBH(4)
title_full Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)(3) and NaBH(4)
title_fullStr Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)(3) and NaBH(4)
title_full_unstemmed Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)(3) and NaBH(4)
title_short Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)(3) and NaBH(4)
title_sort iron-catalysed, general and operationally simple formal hydrogenation using fe(otf)(3) and nabh(4)
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4295815/
https://www.ncbi.nlm.nih.gov/pubmed/24914735
http://dx.doi.org/10.1039/c4ob00945b
work_keys_str_mv AT macnairalistairj ironcatalysedgeneralandoperationallysimpleformalhydrogenationusingfeotf3andnabh4
AT tranmingming ironcatalysedgeneralandoperationallysimpleformalhydrogenationusingfeotf3andnabh4
AT nelsonjennifere ironcatalysedgeneralandoperationallysimpleformalhydrogenationusingfeotf3andnabh4
AT sloangusherwood ironcatalysedgeneralandoperationallysimpleformalhydrogenationusingfeotf3andnabh4
AT ironmongeralan ironcatalysedgeneralandoperationallysimpleformalhydrogenationusingfeotf3andnabh4
AT thomasstephenp ironcatalysedgeneralandoperationallysimpleformalhydrogenationusingfeotf3andnabh4

Ejemplares similares