ArticleChemical science2018
Mechanistic insights into boron-catalysed direct amidation reactions.
Article in Chemical science, 2018. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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13 citing papers in PubMed, 115 citations in OpenAlex.
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- On the Use of Triarylsilanols as Catalysts for Direct Amidation of Carboxylic Acids.The Journal of organic chemistry · 2023Article
- Reaction Optimization for Greener Chemistry with a Comprehensive Spreadsheet Tool.Molecules (Basel, Switzerland) · 2022Article
- Methyltrimethoxysilane (MTM) as a Reagent for Direct Amidation of Carboxylic Acids.Organic letters · 2022Article
- Stereoselective Syntheses of 3'-Hydroxyamino- and 3'-Methoxyamino-2',3'-Dideoxynucleosides.Organic letters · 2019Article
- Formamide catalyzed activation of carboxylic acids - versatile and cost-efficient amidation and esterification.Chemical science · 2019Article
- Catalytic direct amidations in tert-butyl acetate using B(OCHOrganic & biomolecular chemistry · 2019Article
- Protecting-Group-Free Amidation of Amino Acids using Lewis Acid Catalysts.Chemistry (Weinheim an der Bergstrasse, Germany) · 2018Article
Corrections and comments
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Authors and funding
7 authors at 2 institutions in 2 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The generally accepted monoacyloxyboron mechanism of boron-catalysed direct amidation is brought into question in this study, and new alternatives are proposed. We have carried out a detailed investigation of boron-catalysed amidation reactions, through study of the interaction between amines/carboxylic acids and borinic acids, boronic acids and boric acid, and have isolated and characterised by NMR/X-ray crystallography many of the likely intermediates present in catalytic amidation reactions. Rapid reaction between amines and boron compounds was observed in all cases, and it is proposed that such boron-nitrogen interactions are highly likely to take place in catalytic amidation reactions. These studies also clearly show that borinic acids are not competent catalysts for amidation, as they either form unreactive amino-carboxylate complexes, or undergo protodeboronation to give boronic acids. It therefore seems that at least three free coordination sites on the boron atom are necessary for amidation catalysis to occur. However, these observations are not consistent with the currently accepted 'mechanism' for boron-mediated amidation reactions involving nucleophilic attack of an amine onto a monomeric acyloxyboron intermediate, and as a result of our observations and theoretical modelling, alternative proposed mechanisms are presented for boron-mediated amidation reactions. These are likely to proceed
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