The mechanism of thio acid/azide amidation and application to thioamide synthesis

ORGN 610

Robert V. Kolakowski, Ning Shangguan, Kristin Barlett, and Lawrence J. Williams. Department of Chemistry and Chemical Biology, Rutgers University, 610 Taylor Rd, Piscataway, NJ 08854
Thio acid/azide coupling reaction that can result in the formation of amide bonds in high yields. The mechanism of amidation reported herein was experimentally determined to proceed via a thiatriazoline intermediate. This reaction and mechanistic framework was extended to dithio acids and azides yielding the corresponding thioamides under mild condition and was shown to be effective in water.