Bi-mediated allylation of aldehydes in [bmim][Br]: a mechanistic investigation

The inexpensive room temperature ionic liquid (RTIL), [bmim][Br] has been found to be a superior medium for the Bi-mediated Barbier-type allylation of aldehydes compared to other conventional solvents. It plays the dual role of a solvent and a metal activator enabling higher yields of the products i...

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Autores principales: Koli, Mrunesh, Chatterjee, Sucheta, Chattopadhyay, Subrata, Goswami, Dibakar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6122318/
https://www.ncbi.nlm.nih.gov/pubmed/30202472
http://dx.doi.org/10.3762/bjoc.14.193
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author Koli, Mrunesh
Chatterjee, Sucheta
Chattopadhyay, Subrata
Goswami, Dibakar
author_facet Koli, Mrunesh
Chatterjee, Sucheta
Chattopadhyay, Subrata
Goswami, Dibakar
author_sort Koli, Mrunesh
collection PubMed
description The inexpensive room temperature ionic liquid (RTIL), [bmim][Br] has been found to be a superior medium for the Bi-mediated Barbier-type allylation of aldehydes compared to other conventional solvents. It plays the dual role of a solvent and a metal activator enabling higher yields of the products in a shorter reaction time using stoichiometric/near-stoichiometric amounts of reagents. Plausibly, [bmim][Br] activates Bi metal by a charge transfer mechanism. The (1)H VT-NMR studies suggested that both the allylating species, allylbismuth dibromide and diallylbismuth bromide, are generated in situ.
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spelling pubmed-61223182018-09-10 Bi-mediated allylation of aldehydes in [bmim][Br]: a mechanistic investigation Koli, Mrunesh Chatterjee, Sucheta Chattopadhyay, Subrata Goswami, Dibakar Beilstein J Org Chem Full Research Paper The inexpensive room temperature ionic liquid (RTIL), [bmim][Br] has been found to be a superior medium for the Bi-mediated Barbier-type allylation of aldehydes compared to other conventional solvents. It plays the dual role of a solvent and a metal activator enabling higher yields of the products in a shorter reaction time using stoichiometric/near-stoichiometric amounts of reagents. Plausibly, [bmim][Br] activates Bi metal by a charge transfer mechanism. The (1)H VT-NMR studies suggested that both the allylating species, allylbismuth dibromide and diallylbismuth bromide, are generated in situ. Beilstein-Institut 2018-08-22 /pmc/articles/PMC6122318/ /pubmed/30202472 http://dx.doi.org/10.3762/bjoc.14.193 Text en Copyright © 2018, Koli et al. https://creativecommons.org/licenses/by/4.0https://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/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. 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
Koli, Mrunesh
Chatterjee, Sucheta
Chattopadhyay, Subrata
Goswami, Dibakar
Bi-mediated allylation of aldehydes in [bmim][Br]: a mechanistic investigation
title Bi-mediated allylation of aldehydes in [bmim][Br]: a mechanistic investigation
title_full Bi-mediated allylation of aldehydes in [bmim][Br]: a mechanistic investigation
title_fullStr Bi-mediated allylation of aldehydes in [bmim][Br]: a mechanistic investigation
title_full_unstemmed Bi-mediated allylation of aldehydes in [bmim][Br]: a mechanistic investigation
title_short Bi-mediated allylation of aldehydes in [bmim][Br]: a mechanistic investigation
title_sort bi-mediated allylation of aldehydes in [bmim][br]: a mechanistic investigation
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6122318/
https://www.ncbi.nlm.nih.gov/pubmed/30202472
http://dx.doi.org/10.3762/bjoc.14.193
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AT goswamidibakar bimediatedallylationofaldehydesinbmimbramechanisticinvestigation

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