Silver-Catalyzed para-Selective Sulfenyl Group Transfer Reactions of N-Sulfenylanilides

Itaru Nakamura; Ichiro Muranushi; Takato Asoh; Masahiro Terada

doi:10.1002/chem.202301751

Silver-Catalyzed para-Selective Sulfenyl Group Transfer Reactions of N-Sulfenylanilides

Chemistry. 2023 Sep 21;29(53):e202301751. doi: 10.1002/chem.202301751. Epub 2023 Aug 21.

Authors

Itaru Nakamura¹, Ichiro Muranushi², Takato Asoh², Masahiro Terada²

Affiliations

¹ Research and Analytical Center for Giant Molecules Graduate School of Science, Tohoku University, 6-3 Aramaki Aza Aoba, Aoba-ku, Sendai, 980-8578, Japan.
² Department of Chemistry, Graduate School of Science, Tohoku University, 6-3 Aramaki Aza Aoba, Aoba-ku, Sendai, 980-8578, Japan.

PMID: 37409634
DOI: 10.1002/chem.202301751

Abstract

Silver-catalyzed reactions of N-sulfenylanilides afforded the corresponding p-sulfenylanilides in good to high yields with good para selectivity. The transformation has a high compatibility of functional groups, such as ester, bromo, and iodo groups. Mechanistic studies indicate that the rearrangement reaction proceeds through intermolecular transfer of the sulfenyl group.

Keywords: anilines; group transfer; rearrangements; silver; sulfur.