Controlled thioamide vs. amide formation in the thioacid-azide reaction under acidic aqueous conditions.

@article{Mhlberg2014ControlledTV,
  title={Controlled thioamide vs. amide formation in the thioacid-azide reaction under acidic aqueous conditions.},
  author={Michaela M{\"u}hlberg and Kristina D Siebertz and Brigitte Schlegel and Peter Schmieder and Christian P R Hackenberger},
  journal={Chemical communications},
  year={2014},
  volume={50 35},
  pages={4603-6}
}
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.