Synthesis of Sulfimides and <i>N-</i>Allyl-<i>N-</i>(thio)amides by Ru(II)-Catalyzed Nitrene Transfer Reactions of <i>N-</i>Acyloxyamides
Xinyu Zhang, Bo Lin, Jianhui Chen, Jiajia Chen, Yanshu Luo, Yuanzhi Xia
Abstract
The N-acyloxyamides were employed as effective N-acyl nitrene precursors in reactions with thioethers under the catalysis of a commercially available Ru(II) complex, from which a variety of sulfimides were synthesized efficiently and mildly. If an allyl group is contained in the thioether precursor, the [2,3]-sigmatropic rearrangement of the sulfimide occurs simultaneously and the N-allyl-N-(thio)amides were obtained as the final products. Preliminary mechanistic studies indicated that the Ru-nitrenoid species should be a key intermediate in the transformation.
Topics & Concepts
NitreneChemistryThioetherThio-CatalysisMedicinal chemistryStereochemistryOrganic chemistrySynthesis and Catalytic ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods