Hydrogenation of unactivated enamines to tertiary amines: rhodium complexes of fluorinated phosphines give marked improvements in catalytic activity

In the hydrogenation of sluggish unactivated enamine substrates, Rh complexes of electron-deficient phosphines are demonstrated to be far more reactive catalysts than those derived from triphenylphosphine. These operate at low catalyst loadings (down to 0.01 mol %) and are able to reduce tetrasubsti...

Descripción completa

Detalles Bibliográficos
Autores principales: Tin, Sergey, Fanjul, Tamara, Clarke, Matthew L
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4464316/
https://www.ncbi.nlm.nih.gov/pubmed/26124864
http://dx.doi.org/10.3762/bjoc.11.70
_version_ 1782375940314103808
author Tin, Sergey
Fanjul, Tamara
Clarke, Matthew L
author_facet Tin, Sergey
Fanjul, Tamara
Clarke, Matthew L
author_sort Tin, Sergey
collection PubMed
description In the hydrogenation of sluggish unactivated enamine substrates, Rh complexes of electron-deficient phosphines are demonstrated to be far more reactive catalysts than those derived from triphenylphosphine. These operate at low catalyst loadings (down to 0.01 mol %) and are able to reduce tetrasubstituted enamines. The use of the sustainable and environmentally benign solvent (R)-limonene for the reaction is also reported with the amine isolated by acid extraction.
format Online
Article
Text
id pubmed-4464316
institution National Center for Biotechnology Information
language English
publishDate 2015
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-44643162015-06-29 Hydrogenation of unactivated enamines to tertiary amines: rhodium complexes of fluorinated phosphines give marked improvements in catalytic activity Tin, Sergey Fanjul, Tamara Clarke, Matthew L Beilstein J Org Chem Full Research Paper In the hydrogenation of sluggish unactivated enamine substrates, Rh complexes of electron-deficient phosphines are demonstrated to be far more reactive catalysts than those derived from triphenylphosphine. These operate at low catalyst loadings (down to 0.01 mol %) and are able to reduce tetrasubstituted enamines. The use of the sustainable and environmentally benign solvent (R)-limonene for the reaction is also reported with the amine isolated by acid extraction. Beilstein-Institut 2015-05-05 /pmc/articles/PMC4464316/ /pubmed/26124864 http://dx.doi.org/10.3762/bjoc.11.70 Text en Copyright © 2015, Tin et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Tin, Sergey
Fanjul, Tamara
Clarke, Matthew L
Hydrogenation of unactivated enamines to tertiary amines: rhodium complexes of fluorinated phosphines give marked improvements in catalytic activity
title Hydrogenation of unactivated enamines to tertiary amines: rhodium complexes of fluorinated phosphines give marked improvements in catalytic activity
title_full Hydrogenation of unactivated enamines to tertiary amines: rhodium complexes of fluorinated phosphines give marked improvements in catalytic activity
title_fullStr Hydrogenation of unactivated enamines to tertiary amines: rhodium complexes of fluorinated phosphines give marked improvements in catalytic activity
title_full_unstemmed Hydrogenation of unactivated enamines to tertiary amines: rhodium complexes of fluorinated phosphines give marked improvements in catalytic activity
title_short Hydrogenation of unactivated enamines to tertiary amines: rhodium complexes of fluorinated phosphines give marked improvements in catalytic activity
title_sort hydrogenation of unactivated enamines to tertiary amines: rhodium complexes of fluorinated phosphines give marked improvements in catalytic activity
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4464316/
https://www.ncbi.nlm.nih.gov/pubmed/26124864
http://dx.doi.org/10.3762/bjoc.11.70
work_keys_str_mv AT tinsergey hydrogenationofunactivatedenaminestotertiaryaminesrhodiumcomplexesoffluorinatedphosphinesgivemarkedimprovementsincatalyticactivity
AT fanjultamara hydrogenationofunactivatedenaminestotertiaryaminesrhodiumcomplexesoffluorinatedphosphinesgivemarkedimprovementsincatalyticactivity
AT clarkematthewl hydrogenationofunactivatedenaminestotertiaryaminesrhodiumcomplexesoffluorinatedphosphinesgivemarkedimprovementsincatalyticactivity

Ejemplares similares