Chemoselective N-acetylation of primary aliphatic amines promoted by pivalic or acetic acid using ethyl acetate as an acetyl donor. Issue 12 (22nd March 2017)

• Record Type: Journal Article
• Authors: Yoshida, Tomoki; Kawamura, Shimpei; Nakata, Kenya
• Is Part Of: Tetrahedron letters. Volume 58:Issue 12(2017)
• Page Start: 1181
• Page End: 1184
• Publication Date: 2017-03-22
• Subjects: N-acetylation -- Acetamide -- Primary aliphatic amines -- Pivalic acid -- Chemoselective; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.02.015
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A chemoselective N-acetylation of primary aliphatic amines was achieved. Ethyl acetate was used as an acetyl donor. This method is very simple and convenient for the preparation of acetamides. Abstract: The combination of pivalic or acetic acid as a promoter and EtOAc as a solvent and acetyl donor proved to be efficient for the chemoselective N-acetylation of primary aliphatic amines to afford the corresponding acetamides. We developed a simple and convenient approach, which requires mild reaction conditions. Competitive inter- and intramolecular reactions between aliphatic amines, alcohols, and aromatic amines were examined, and chemoselectivity was achieved by adjusting the conditions of the reaction.