A Rapid, Mild and Direct Route to Sulfonimidoyl Fluoride from Sulfenamide

Padma Priya V R; Antony Haritha Mercy A; Natarajan K; Sugapriya S; Ganesh Chandra Nandi

doi:10.1021/acs.joc.4c01644

A Rapid, Mild and Direct Route to Sulfonimidoyl Fluoride from Sulfenamide

J Org Chem. 2024 Oct 30. doi: 10.1021/acs.joc.4c01644. Online ahead of print.

Authors

Padma Priya V R¹, Antony Haritha Mercy A¹, Natarajan K¹, Sugapriya S¹, Ganesh Chandra Nandi¹

Affiliation

¹ Department of Chemistry, National Institute of Technology, Tiruchirappalli, Tamilnadu 620015, India.

PMID: 39478286
DOI: 10.1021/acs.joc.4c01644

Abstract

We develop a rapid and mild protocol to access sulfonimidoyl fluoride-[S(VI)] from sulfenamide-[S(II)] directly. The transformation occurs via the reaction of sulfenamide with NCS (N-chlorosuccinimide), water, and TBAF in acetonitrile. Water and TBAF act as the source for S═O bond formation and fluoride, respectively. The reaction takes a very short time (within 5 min). The drug molecules, such as Carbamazepine and Levetiracetam attached sulfonimidoyl fluorides are also achieved following this protocol. Furthermore, sulfonimidoyl fluoride is transformed into sulfonimidamide in the presence of AlCl₃. To the best of our knowledge, it is the first report detailing the synthesis of sulfonimidoyl fluoride-[S(VI)] directly from S(II)-sulfenamide.