ArticleOrganic & biomolecular chemistry2019
Catalytic direct amidations in tert-butyl acetate using B(OCH
Article in Organic & biomolecular chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 39 citations in OpenAlex.
- Small Molecule Catalyst for Peptide Synthesis.Journal of the American Chemical Society · 2025Article
- Emergent Organoboron Acid Catalysts.The Journal of organic chemistry · 2024Review
- Reactivity-based identification of oxygen containing functional groups of chemicals applied as potential classifier in non-target analysis.Scientific reports · 2023Article
- On the Use of Triarylsilanols as Catalysts for Direct Amidation of Carboxylic Acids.The Journal of organic chemistry · 2023Article
- Chemical Wastes in the Peptide Synthesis Process and Ways to Reduce Them.Iranian journal of pharmaceutical research : IJPR · 2022Review
- Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives.Chemical reviews · 2022Review
- Methyltrimethoxysilane (MTM) as a Reagent for Direct Amidation of Carboxylic Acids.Organic letters · 2022Article
- Copper-catalyzed transformation of alkyl nitriles toRSC advances · 2021Article
- Formamide catalyzed activation of carboxylic acids - versatile and cost-efficient amidation and esterification.Chemical science · 2019Article
Corrections and comments
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Authors and funding
7 authors at 2 institutions in 2 countries.
Funding
Abstract
Catalytic direct amidation reactions have been the focus of considerable recent research effort, due to the widespread use of amide formation processes in pharmaceutical synthesis. However, the vast majority of catalytic amidations are performed in non-polar solvents (aromatic hydrocarbons, ethers) which are typically undesirable from a sustainability perspective, and are often poor at solubilising polar carboxylic acid and amine substrates. As a consequence, most catalytic amidation protocols are unsuccessful when applied to polar and/or functionalised substrates of the kind commonly used in medicinal chemistry. In this paper we report a practical and useful catalytic direct amidation reaction using tert-butyl acetate as the reaction solvent. The use of an ester solvent offers improvements in terms of safety and sustainability, but also leads to an improved reaction scope with regard to polar substrates and less nucleophilic anilines, both of which are important components of amides used in medicinal chemistry. An amidation reaction was scaled up to 100 mmol and proceeded with excellent yield and efficiency, with a measured process mass intensity of 8.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.