Title:Metal-Free Selective para-Tosyloxylation of N-Arylbenzamides using [Hydroxy(tosyloxy)iodo]benzene
Volume: 21
Issue: 5
Author(s): Neha Rani, Deepak Kumar Aneja*, Mayank Kinger*, Rinku Soni, Monika Sihag and Sandeep Malik
Affiliation:
- Department of Chemistry, Chaudhary Bansi Lal University, Bhiwani, 127021, Haryana, India
- Department of Chemistry, Chaudhary Bansi Lal University, Bhiwani, 127021, Haryana, India
Keywords:
Hypervalent iodine reagent, HTIB, tosyloxylation, tosyloxyl group, room temperature, reaction, Nphenylbenzamide, group-transfer, metal-free.
Abstract: An efficient approach for the tosyloxyl group transfer in several N-arylbenzamides has been
achieved using HTIB (Koser’s reagent) under mild reaction conditions. Its simplicity, efficiency, and
reduced reliance on hazardous reagents make it an attractive choice for chemists seeking sustainable
alternatives. The proposed methodology offered single-step para-selective tosyloxylation, ensuring the
prevention of the synthesis of mixtures of ortho and meta-isomers. The corresponding products were
obtained with moderate to excellent efficiency. The current approach eliminated the need for harsh,
acidic, and toxic metals, ensuring safer handling and minimizing environmental impact. A plausible
mechanism for tosyloxylation of N-arylbenzamides involving iodonium ylide has been proposed.