Categories: N-S Bond Formation >
Synthesis of Sulfenamides
The copper-catalyzed coupling of diaryl disulfides with alkyl amines affords various sulfenamides in good yields. Furthermore, both aryl groups of the disulfide reacted effectively.
N. Taniguchi, Synlett, 2007, 1917-1920.
N-Trifluoroacetyl arenesulfenamides are effective precursors for the synthesis of unsymmetrical disulfides and sulfenamides. Reactions of N-trifluoroacetyl arenesulfenamides with thiols and amines gave the desired products in high yields within short reaction times.
M. Bao, M. Shimizu, Tetrahedron, 2003, 59, 9655-9659.
A commercially available Ru(II) complex catalyzes an efficient and mild reaction of thioethers with N-acyloxyamides as N-acyl nitrene precursors to provide sulfimides. If allylic sulfides are used as starting materials, a [2,3]-sigmatropic rearrangement of the sulfimide intermediate gives N-allyl-N-(thio)amides. Preliminary mechanistic studies indicated that a Ru-nitrenoid species is a key intermediate.
X. Zhang, B. Lin, J. Chen, J. Chen, Y. Luo, Y. Xia, Org. Lett., 2021, 23, 819-825.