Direct formation of amide/peptide bonds from carboxylic acids: no traditional coupling reagents, 1-pot, and green

Kaitlyn M Freiberg; Rahul D Kavthe; Rohan M Thomas; David M Fialho; Paris Dee; Matthew Scurria; Bruce H Lipshutz

doi:10.1039/d3sc00198a

Direct formation of amide/peptide bonds from carboxylic acids: no traditional coupling reagents, 1-pot, and green

Chem Sci. 2023 Feb 28;14(13):3462-3469. doi: 10.1039/d3sc00198a. eCollection 2023 Mar 29.

Authors

Kaitlyn M Freiberg¹, Rahul D Kavthe¹, Rohan M Thomas¹, David M Fialho¹, Paris Dee¹, Matthew Scurria¹, Bruce H Lipshutz¹

Affiliation

¹ Department of Chemistry and Biochemistry, University of California Santa Barbara CA 93106 USA [email protected].

Abstract

Technology for generating especially important amide and peptide bonds from carboxylic acids and amines that avoids traditional coupling reagents is described. The 1-pot processes developed rely on thioester formation, neat, using a simple dithiocarbamate, and are safe and green, and rely on Nature-inspired thioesters that are then converted to the targeted functionality.