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Synthesis of diverse libraries of carboxamides via chemoselective N-acylation of amines by carboxylic acids employing Brønsted acidic IL [BMIM(SO3H)][OTf]

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Abstract Chemoselective N-acylation of amines with carboxylic acids as acyl electrophiles and Bronsted acidic IL [BMIM(SO3H)][OTf] as promoter is reported under both thermal and microwave irradiation to produce libraries of… Click to show full abstract

Abstract Chemoselective N-acylation of amines with carboxylic acids as acyl electrophiles and Bronsted acidic IL [BMIM(SO3H)][OTf] as promoter is reported under both thermal and microwave irradiation to produce libraries of carboxamides in good to excellent yields after a simple workup. The protocol is compatible with structurally diverse 1° and 2° amines and works in the presence of sensitive functional groups such as thiols and phenols. The potential for recycling and reuse of the IL is also demonstrated.

Keywords: bmim so3h; amines carboxylic; carboxylic acids; acidic bmim; acylation amines; chemoselective acylation

Journal Title: Tetrahedron Letters
Year Published: 2019

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