Exhaustive Reduction of Esters, Carboxylic Acids and Carbamates to Methyl Groups Catalyzed by Boronic Acids
Abstract: Carboxy to methyl reduction is an important transformation in organic synthesis, yet existing methodologies often require multi‐step procedures or use hazardous metal hydrides. Herein, a metal‐free catalytic system is reported for the one‐step reduction of esters, carboxylic acids, and carbamates to a methyl group, in the presence of catalytic amounts of boronic acids. By using ammonia borane as a hydrogen donor, a wide range of products bearing different functional groups can be obtained in high yields under relatively mild conditions. Mechanistic studies and control experiments elucidate the complexity of the mechanism and provide an explanation for the observed selectivity.
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Bibliographic citation
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Exhaustive Reduction of Esters, Carboxylic Acids and Carbamates to Methyl Groups Catalyzed by Boronic Acids ; day:09 ; month:11 ; year:2023 ; extent:8
European journal of organic chemistry ; (09.11.2023) (gesamt 8)
- Creator
- DOI
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10.1002/ejoc.202300904
- URN
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urn:nbn:de:101:1-2023111014044301826127
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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14.08.2025, 10:54 AM CEST
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Associated
- Guo, Xuewen
- Zuo, Yujing
- Alvarez, Gustavo A.
- Mejía Vargas, Oscar Esteban
Other Objects (12)
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Reactions of Carboxylic Acids
Preparation of Carboxylic Acids
Synthesis of Anilines from Boronic Acids
Boronic Acid Catalyzed Dehydrative Peptide Synthesis
Synthesis of Halogenated Carboxylic Acids and Amino Acids
Formose reaction controlled by boronic acid compounds
Synthesis of 2-((quinolin-8-yloxy) methyl) quinoline-3-carboxylic acid derivatives
Applications of the Reversible Boronic Acids/Boronate Switch to Nucleic Acids
Carboxylic Acids
Boronic acids, Vol. 2.
Boronic acids, Vol. 1.
Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid
Reactions of Carboxylic Acids
Preparation of Carboxylic Acids
Synthesis of Anilines from Boronic Acids
Boronic Acid Catalyzed Dehydrative Peptide Synthesis
Synthesis of Halogenated Carboxylic Acids and Amino Acids
Formose reaction controlled by boronic acid compounds
Synthesis of 2-((quinolin-8-yloxy) methyl) quinoline-3-carboxylic acid derivatives
Applications of the Reversible Boronic Acids/Boronate Switch to Nucleic Acids
Carboxylic Acids
Boronic acids, Vol. 2.
Boronic acids, Vol. 1.
Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid
Reactions of Carboxylic Acids
Preparation of Carboxylic Acids
Synthesis of Anilines from Boronic Acids
Boronic Acid Catalyzed Dehydrative Peptide Synthesis
Synthesis of Halogenated Carboxylic Acids and Amino Acids
Formose reaction controlled by boronic acid compounds
Synthesis of 2-((quinolin-8-yloxy) methyl) quinoline-3-carboxylic acid derivatives