2024
DOI: 10.1021/acs.orglett.4c03363
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TCFH–NMI Ketone Synthesis Inspired by Nucleophilicity Scales

Johnson H. Ho,
Grant H. Miller,
Kasey K. Chung
et al.

Abstract: Tetramethylchloroformamidinium hexafluorophosphate (TCFH) and N-methylimidazole (NMI) enable the facile and practical reaction of carboxylic acids with amines, alcohols, and thiols to form amides, esters, and thioesters. To develop a mild synthesis of ketones with TCFH−NMI directly from carboxylic acids at room temperature, the Mayr nucleophilicity scale was used to compare the N values of competent nucleophiles to potential carbon-centered nucleophiles, identifying pyrroles and indoles as successful substrate… Show more

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