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Synthesis of Sulfimides and N-Allyl-N-(thio)amides by Ru(II)-Catalyzed Nitrene Transfer Reactions of N-Acyloxyamides

Xinyu Zhang, Bo Lin, Jianhui Chen, Jiajia Chen, Yanshu Luo and Yuanzhi Xia*

*College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, China, Email:

X. Zhang, B. Lin, J. Chen, J. Chen, Y. Luo, Y. Xia, Org. Lett., 2021, 23, 819-825.

DOI: 10.1021/acs.orglett.0c04043

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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.

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proposed mechanism

Key Words

sulfimides, sulfenamides

ID: J54-Y2021