Cargando…

Continuous-flow synthesis of primary amines: Metal-free reduction of aliphatic and aromatic nitro derivatives with trichlorosilane

The metal-free reduction of nitro compounds to amines mediated by trichlorosilane was successfully performed for the first time under continuous-flow conditions. Aromatic as well as aliphatic nitro derivatives were converted to the corresponding primary amines in high yields and very short reaction...

Descripción completa

Detalles Bibliográficos
Autores principales: Porta, Riccardo, Puglisi, Alessandra, Colombo, Giacomo, Rossi, Sergio, Benaglia, Maurizio
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238609/
https://www.ncbi.nlm.nih.gov/pubmed/28144331
http://dx.doi.org/10.3762/bjoc.12.257
_version_ 1782495736478302208
author Porta, Riccardo
Puglisi, Alessandra
Colombo, Giacomo
Rossi, Sergio
Benaglia, Maurizio
author_facet Porta, Riccardo
Puglisi, Alessandra
Colombo, Giacomo
Rossi, Sergio
Benaglia, Maurizio
author_sort Porta, Riccardo
collection PubMed
description The metal-free reduction of nitro compounds to amines mediated by trichlorosilane was successfully performed for the first time under continuous-flow conditions. Aromatic as well as aliphatic nitro derivatives were converted to the corresponding primary amines in high yields and very short reaction times with no need for purification. The methodology was also extended to the synthesis of two synthetically relevant intermediates (precursors of baclofen and boscalid).
format Online
Article
Text
id pubmed-5238609
institution National Center for Biotechnology Information
language English
publishDate 2016
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-52386092017-01-31 Continuous-flow synthesis of primary amines: Metal-free reduction of aliphatic and aromatic nitro derivatives with trichlorosilane Porta, Riccardo Puglisi, Alessandra Colombo, Giacomo Rossi, Sergio Benaglia, Maurizio Beilstein J Org Chem Full Research Paper The metal-free reduction of nitro compounds to amines mediated by trichlorosilane was successfully performed for the first time under continuous-flow conditions. Aromatic as well as aliphatic nitro derivatives were converted to the corresponding primary amines in high yields and very short reaction times with no need for purification. The methodology was also extended to the synthesis of two synthetically relevant intermediates (precursors of baclofen and boscalid). Beilstein-Institut 2016-12-05 /pmc/articles/PMC5238609/ /pubmed/28144331 http://dx.doi.org/10.3762/bjoc.12.257 Text en Copyright © 2016, Porta 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), 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
Porta, Riccardo
Puglisi, Alessandra
Colombo, Giacomo
Rossi, Sergio
Benaglia, Maurizio
Continuous-flow synthesis of primary amines: Metal-free reduction of aliphatic and aromatic nitro derivatives with trichlorosilane
title Continuous-flow synthesis of primary amines: Metal-free reduction of aliphatic and aromatic nitro derivatives with trichlorosilane
title_full Continuous-flow synthesis of primary amines: Metal-free reduction of aliphatic and aromatic nitro derivatives with trichlorosilane
title_fullStr Continuous-flow synthesis of primary amines: Metal-free reduction of aliphatic and aromatic nitro derivatives with trichlorosilane
title_full_unstemmed Continuous-flow synthesis of primary amines: Metal-free reduction of aliphatic and aromatic nitro derivatives with trichlorosilane
title_short Continuous-flow synthesis of primary amines: Metal-free reduction of aliphatic and aromatic nitro derivatives with trichlorosilane
title_sort continuous-flow synthesis of primary amines: metal-free reduction of aliphatic and aromatic nitro derivatives with trichlorosilane
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238609/
https://www.ncbi.nlm.nih.gov/pubmed/28144331
http://dx.doi.org/10.3762/bjoc.12.257
work_keys_str_mv AT portariccardo continuousflowsynthesisofprimaryaminesmetalfreereductionofaliphaticandaromaticnitroderivativeswithtrichlorosilane
AT puglisialessandra continuousflowsynthesisofprimaryaminesmetalfreereductionofaliphaticandaromaticnitroderivativeswithtrichlorosilane
AT colombogiacomo continuousflowsynthesisofprimaryaminesmetalfreereductionofaliphaticandaromaticnitroderivativeswithtrichlorosilane
AT rossisergio continuousflowsynthesisofprimaryaminesmetalfreereductionofaliphaticandaromaticnitroderivativeswithtrichlorosilane
AT benagliamaurizio continuousflowsynthesisofprimaryaminesmetalfreereductionofaliphaticandaromaticnitroderivativeswithtrichlorosilane