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.

Titel
Controlled thioamide vs. amide formation in the thioacid–azide reaction under acidic aqueous conditions
Verfasser
M. Mühlberg, K.D. Siebertz, B. Schlegel, P. Schmieder, C. P. R. Hackenberger
Datum
2014
Kennung
10.1039/c4cc00774c
Zitierweise
Chem. Commun.,2014, 50, 4603--4606
Art
Text
dfg_logo