Categories: N=S Bond Formation >
Synthesis of sulfilimines
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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.
A facile and efficient multicomponent reaction of arynes, sulfamides, and
thiosulfonates provides a broad range of sulfilimines in very good yields. This
protocol could be conducted on a gram scale, and the products were easily
converted to sulfides and sulfoximines. Mechanism studies revealed that a
sulfenamide generated in situ is the key intermediate for the reaction.
P. Xie, Y. Zheng, Y. Luo, J. Luo, L. Wu, Z. Cai, L. He, Org. Lett., 2023, 25,
6133-6138.
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.
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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.