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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...

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Autores principales: Antico, Emanuele, Schlichter, Peter, Werlé, Christophe, Leitner, Walter
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
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.
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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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