Categories: N=S Bond Formation >
Synthesis of sulfilimines
| Related |
 |
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.
