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Reduction of Carboxylic Acids to Alcohols via Manganese(I) Catalyzed Hydrosilylation
[Image: see text] The reduction of carboxylic acids to the respective alcohols, in mild conditions, was achieved using [MnBr(CO)(5)] as the catalyst and bench stable PhSiH(3) as the reducing agent. It was shown that the reaction with the earth-abundant metal catalyst could be performed either with a...
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/PMC8395667/ https://www.ncbi.nlm.nih.gov/pubmed/34467330 http://dx.doi.org/10.1021/jacsau.1c00140 |
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author | Antico, Emanuele Schlichter, Peter Werlé, Christophe Leitner, Walter |
author_facet | Antico, Emanuele Schlichter, Peter Werlé, Christophe Leitner, Walter |
author_sort | Antico, Emanuele |
collection | PubMed |
description | [Image: see text] The reduction of carboxylic acids to the respective alcohols, in mild conditions, was achieved using [MnBr(CO)(5)] as the catalyst and bench stable PhSiH(3) as the reducing agent. It was shown that the reaction with the earth-abundant metal catalyst could be performed either with a catalyst loading as low as 0.5 mol %, rare with the use of [MnBr(CO)(5)], or on a gram scale employing only 1.5 equiv of PhSiH(3), the lowest amount of silane reported to date for this transformation. Kinetic data and control experiments have provided initial insight into the mechanism of the catalytic process, suggesting that it proceeds via the formation of silyl ester intermediates and ligand dissociation to generate a coordinatively unsaturated Mn(I) complex as the active species. |
format | Online Article Text |
id | pubmed-8395667 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | American
Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-83956672021-08-30 Reduction of Carboxylic Acids to Alcohols via Manganese(I) Catalyzed Hydrosilylation Antico, Emanuele Schlichter, Peter Werlé, Christophe Leitner, Walter JACS Au [Image: see text] The reduction of carboxylic acids to the respective alcohols, in mild conditions, was achieved using [MnBr(CO)(5)] as the catalyst and bench stable PhSiH(3) as the reducing agent. It was shown that the reaction with the earth-abundant metal catalyst could be performed either with a catalyst loading as low as 0.5 mol %, rare with the use of [MnBr(CO)(5)], or on a gram scale employing only 1.5 equiv of PhSiH(3), the lowest amount of silane reported to date for this transformation. Kinetic data and control experiments have provided initial insight into the mechanism of the catalytic process, suggesting that it proceeds via the formation of silyl ester intermediates and ligand dissociation to generate a coordinatively unsaturated Mn(I) complex as the active species. American Chemical Society 2021-05-11 /pmc/articles/PMC8395667/ /pubmed/34467330 http://dx.doi.org/10.1021/jacsau.1c00140 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 | Antico, Emanuele Schlichter, Peter Werlé, Christophe Leitner, Walter Reduction of Carboxylic Acids to Alcohols via Manganese(I) Catalyzed Hydrosilylation |
title | Reduction of Carboxylic Acids to Alcohols via Manganese(I)
Catalyzed Hydrosilylation |
title_full | Reduction of Carboxylic Acids to Alcohols via Manganese(I)
Catalyzed Hydrosilylation |
title_fullStr | Reduction of Carboxylic Acids to Alcohols via Manganese(I)
Catalyzed Hydrosilylation |
title_full_unstemmed | Reduction of Carboxylic Acids to Alcohols via Manganese(I)
Catalyzed Hydrosilylation |
title_short | Reduction of Carboxylic Acids to Alcohols via Manganese(I)
Catalyzed Hydrosilylation |
title_sort | reduction of carboxylic acids to alcohols via manganese(i)
catalyzed hydrosilylation |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8395667/ https://www.ncbi.nlm.nih.gov/pubmed/34467330 http://dx.doi.org/10.1021/jacsau.1c00140 |
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