Amide Synthesis Through the In Situ Generation of Chloro- and Imido-Phosphonium Salts

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2020 Jul 9

PMID 32637849

Citations 1

Authors

Charles D Irving

Jack T Floreancig

Sebastien Laulhe

Affiliations

Soon will be listed here.

Abstract

We describe a methodology for the amidation of carboxylic acids by generating phosphonium salts in situ from -chlorophthalimide and triphenylphosphine. Aliphatic, benzylic, and aromatic carboxylic acids can be transformed into their amide counter parts using primary and secondary amines. This functional group interconversion is achieved at room temperature in good to excellent yields. Mechanistic work shows the in situ formation of chloro- and imido-phosphonium salts that react as activating agents for carboxylic acids and generate an acyloxy-phosphonium species.

Citing Articles

Synthesis of Imide and Amine Derivatives via Deoxyamination of Alcohols Using -Haloimides and Triphenylphosphine.

Irving C, Floreancig J, Gasonoo M, Kelley A, Laulhe S ChemistrySelect. 2023; 6(33):8874-8878.

PMID: 37207246 PMC: 10195045. DOI: 10.1002/slct.202102296.

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