Controlled thioamide vs. amide formation in the thioacid–azide reaction under acidic aqueous conditions
M. Mühlberg, K.D. Siebertz, B. Schlegel, P. Schmieder, C. P. R. Hackenberger – 2014
The thioacid–azide reaction and its chemoselectivity were probed with alkyl azides for a potential application to form amide bonds in aqueous solvents. Our results reveal that under acidic conditions thioamides were formed as major reaction products suggesting a competing mechanism, whereas reactions forming amides predominated at slightly higher pH values.