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Catalytic direct amidations in tert-butyl acetate using B(OCH2CF3)3

Coomber, CE; Laserna, V; Martin, LT; Smith, PD; Hailes, HC; Porter, MJ; Sheppard, TD; (2019) Catalytic direct amidations in tert-butyl acetate using B(OCH2CF3)3. Organic and Biomolecular Chemistry , 17 (26) pp. 6465-6469. 10.1039/c9ob01012b. Green open access

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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.

Type: Article
Title: Catalytic direct amidations in tert-butyl acetate using B(OCH2CF3)3
Open access status: An open access version is available from UCL Discovery
DOI: 10.1039/c9ob01012b
Publisher version: https://doi.org/10.1039/C9OB01012B
Language: English
Additional information: This journal is © The Royal Society of Chemistry 2019. This article is licensed under a Creative Commons Attribution 3.0 Unported licence (CC BY 3.0).
UCL classification: UCL
UCL > Provost and Vice Provost Offices > UCL BEAMS
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences
UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry
URI: https://discovery.ucl.ac.uk/id/eprint/10077311
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