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Triarylborane Catalyzed Carbene Transfer Reactions Using Diazo Precursors
[Image: see text] Reactive carbenes generated from diazo compounds are key intermediates for a range of organic reactions to afford synthetically useful organic compounds. The majority of these reactions have been carried out using transition metal catalysts. However, the formation of carbene interm...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2021
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8749965/ https://www.ncbi.nlm.nih.gov/pubmed/35028191 http://dx.doi.org/10.1021/acscatal.1c04746 |
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author | Dasgupta, Ayan Richards, Emma Melen, Rebecca L. |
author_facet | Dasgupta, Ayan Richards, Emma Melen, Rebecca L. |
author_sort | Dasgupta, Ayan |
collection | PubMed |
description | [Image: see text] Reactive carbenes generated from diazo compounds are key intermediates for a range of organic reactions to afford synthetically useful organic compounds. The majority of these reactions have been carried out using transition metal catalysts. However, the formation of carbene intermediates using main group elements has not been widely investigated for synthetic purposes. Recent studies have demonstrated that triarylboranes can be used for the in situ generation of reactive carbene intermediates in both stoichiometric and catalytic reactions. These new reactivities of triarylboranes have gained significant attention in synthetic chemistry particularly in catalytic studies. The range of organic compounds that have been synthesized through these reactions are important as pharmaceuticals or agrochemicals. In this perspective, we highlight the recent progress and ongoing challenges of carbene transfer reactions generated from their corresponding diazo precursors using triarylboranes as catalysts. We also highlight the stoichiometric use of triarylboranes in which the boranes not only activate the diazo functionality to afford a carbene intermediate but also actively participate in the reactions as a reagent. The different mechanisms for activation and carbene transfer are described along with the mechanistic and computational studies that have aided the elucidation of these reaction pathways. Potential opportunities for the use of boranes as a catalyst toward different carbene transfer reactions and their future prospects are discussed. |
format | Online Article Text |
id | pubmed-8749965 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-87499652022-01-11 Triarylborane Catalyzed Carbene Transfer Reactions Using Diazo Precursors Dasgupta, Ayan Richards, Emma Melen, Rebecca L. ACS Catal [Image: see text] Reactive carbenes generated from diazo compounds are key intermediates for a range of organic reactions to afford synthetically useful organic compounds. The majority of these reactions have been carried out using transition metal catalysts. However, the formation of carbene intermediates using main group elements has not been widely investigated for synthetic purposes. Recent studies have demonstrated that triarylboranes can be used for the in situ generation of reactive carbene intermediates in both stoichiometric and catalytic reactions. These new reactivities of triarylboranes have gained significant attention in synthetic chemistry particularly in catalytic studies. The range of organic compounds that have been synthesized through these reactions are important as pharmaceuticals or agrochemicals. In this perspective, we highlight the recent progress and ongoing challenges of carbene transfer reactions generated from their corresponding diazo precursors using triarylboranes as catalysts. We also highlight the stoichiometric use of triarylboranes in which the boranes not only activate the diazo functionality to afford a carbene intermediate but also actively participate in the reactions as a reagent. The different mechanisms for activation and carbene transfer are described along with the mechanistic and computational studies that have aided the elucidation of these reaction pathways. Potential opportunities for the use of boranes as a catalyst toward different carbene transfer reactions and their future prospects are discussed. American Chemical Society 2021-12-17 2022-01-07 /pmc/articles/PMC8749965/ /pubmed/35028191 http://dx.doi.org/10.1021/acscatal.1c04746 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Dasgupta, Ayan Richards, Emma Melen, Rebecca L. Triarylborane Catalyzed Carbene Transfer Reactions Using Diazo Precursors |
title | Triarylborane Catalyzed Carbene Transfer Reactions
Using Diazo Precursors |
title_full | Triarylborane Catalyzed Carbene Transfer Reactions
Using Diazo Precursors |
title_fullStr | Triarylborane Catalyzed Carbene Transfer Reactions
Using Diazo Precursors |
title_full_unstemmed | Triarylborane Catalyzed Carbene Transfer Reactions
Using Diazo Precursors |
title_short | Triarylborane Catalyzed Carbene Transfer Reactions
Using Diazo Precursors |
title_sort | triarylborane catalyzed carbene transfer reactions
using diazo precursors |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8749965/ https://www.ncbi.nlm.nih.gov/pubmed/35028191 http://dx.doi.org/10.1021/acscatal.1c04746 |
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