Rh(i)- and Rh(ii)-catalyzed C–H alkylation of benzylamines with alkenes and its application in flow chemistry

The Rh-catalyzed C–H alkylation of benzylamines with alkenes using a picolinamide derivative as a directing group is reported. Both Rh(i) and Rh(ii) complexes can be used as active catalysts for this transformation. In addition, a flow set up was designed to successfully mimic this process under flo...

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Detalles Bibliográficos
Autores principales: Das, Amrita, Chatani, Naoto
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179371/
https://www.ncbi.nlm.nih.gov/pubmed/34164088
http://dx.doi.org/10.1039/d0sc05813k
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author Das, Amrita
Chatani, Naoto
author_facet Das, Amrita
Chatani, Naoto
author_sort Das, Amrita
collection PubMed
description The Rh-catalyzed C–H alkylation of benzylamines with alkenes using a picolinamide derivative as a directing group is reported. Both Rh(i) and Rh(ii) complexes can be used as active catalysts for this transformation. In addition, a flow set up was designed to successfully mimic this process under flow conditions. Several examples are presented under flow conditions and it was confirmed that a flow process is advantageous over a batch process. Deuterium labelling experiments were performed to elucidate the mechanism of the reaction, and the results indicated a possible carbene mechanism for this C–H alkylation process.
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spelling pubmed-81793712021-06-22 Rh(i)- and Rh(ii)-catalyzed C–H alkylation of benzylamines with alkenes and its application in flow chemistry Das, Amrita Chatani, Naoto Chem Sci Chemistry The Rh-catalyzed C–H alkylation of benzylamines with alkenes using a picolinamide derivative as a directing group is reported. Both Rh(i) and Rh(ii) complexes can be used as active catalysts for this transformation. In addition, a flow set up was designed to successfully mimic this process under flow conditions. Several examples are presented under flow conditions and it was confirmed that a flow process is advantageous over a batch process. Deuterium labelling experiments were performed to elucidate the mechanism of the reaction, and the results indicated a possible carbene mechanism for this C–H alkylation process. The Royal Society of Chemistry 2021-01-04 /pmc/articles/PMC8179371/ /pubmed/34164088 http://dx.doi.org/10.1039/d0sc05813k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Das, Amrita
Chatani, Naoto
Rh(i)- and Rh(ii)-catalyzed C–H alkylation of benzylamines with alkenes and its application in flow chemistry
title Rh(i)- and Rh(ii)-catalyzed C–H alkylation of benzylamines with alkenes and its application in flow chemistry
title_full Rh(i)- and Rh(ii)-catalyzed C–H alkylation of benzylamines with alkenes and its application in flow chemistry
title_fullStr Rh(i)- and Rh(ii)-catalyzed C–H alkylation of benzylamines with alkenes and its application in flow chemistry
title_full_unstemmed Rh(i)- and Rh(ii)-catalyzed C–H alkylation of benzylamines with alkenes and its application in flow chemistry
title_short Rh(i)- and Rh(ii)-catalyzed C–H alkylation of benzylamines with alkenes and its application in flow chemistry
title_sort rh(i)- and rh(ii)-catalyzed c–h alkylation of benzylamines with alkenes and its application in flow chemistry
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8179371/
https://www.ncbi.nlm.nih.gov/pubmed/34164088
http://dx.doi.org/10.1039/d0sc05813k
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AT chataninaoto rhiandrhiicatalyzedchalkylationofbenzylamineswithalkenesanditsapplicationinflowchemistry

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