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Synthesis of sulfilimines


Recent Literature

A Cu(OTf)2-catalyzed trifluoroacetamidation of sulfides with a hydroxamic acid anhydride salt provides N-(trifluoroacetyl)sulfilimines. The salient features of this salt include its ease of synthesis from trifluoroacetic anhydride and hydroxylamine hydrochloride as inexpensive, commercially available starting materials.
C. S. Tomooka, D. D. LeCloux, H. Sasaki, E. M. Carreira, Org. Lett., 1999, 1, 149-151.

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.

The synthesis of N-cyanosulfilimines can readily be achieved by reaction of the corresponding sulfides with cyanogen amine in the presence of a base and NBS or I2 as halogenating agents. Oxidation followed by decyanation affords synthetically useful sulfoximines.
O. García Mancheño, O. Bistri, C. Bolm, Org. Lett., 2007, 9, 3809-3811.


A terminal oxidant-free copper-catalyzed dehydrogenative Chan-Lam coupling of free diaryl sulfilimines with arylboronic acids offers excellent chemoselectivity and broad substrate compatibility. This protocol is suitable for late-stage functionalization of complex peptides.
T. Meng, L. A. Wells, T. Wang, J. Wang, S. Zhang, J. Wang, M. C. Kozlowski, T. Jia, J. Am. Chem. Soc., 2022, 144, 12476-12487.