Fast and Efficient Synthesis of Sulfinamides by the Oxidation of Sulfenamides Using Potassium Fluoride and m-Chloroperoxybenzoic Acid

Abstract

A procedure for the synthesis of N-alkyl-, N-cycloalkyl-, N,N-dialkyl-, and N-arylarenesulfinamides from the corresponding sulfenamides using KF/m–chloroperoxybenzoic acid (CPBA) in CH₃CN-H₂O is described. High efficiency (fast reactions, ease of manipulation, and good yields) and absence of overoxidation are the major advantageous features of this protocol.

GRAPHICAL ABSTRACT

Keywords:

• KF/m-CPBA
• oxidation
• sulfenamides
• sulfinamides

ACKNOWLEDGMENT

Financial support from Korea Advanced Institute of Science and Technology (KAIST) is gratefully acknowledged.

Notes

^a Time to completion of reaction, as determined by TLC (silica gel, dichloromethane–hexane [1:1]).

^b Yields refer to chromatographically isolated pure products, which were identified by their spectral characteristics (IR, ¹H NMR, ¹³C NMR, EIMS) and microanalysis (1a–4a) or by comparison of melting point and spectral data with literature data (5a–18a).