Mechanochemical Conditions for Intramolecular N–O Couplings via Rhodium Nitrenoids Generated from N‐Acyl Sulfonimidamides
Pan, S., Wu, P., Bampi, D., Ward, J., Rissanen, K., & Bolm, C. (2024). Mechanochemical Conditions for Intramolecular N–O Couplings via Rhodium Nitrenoids Generated from N‐Acyl Sulfonimidamides. Angewandte Chemie, 63(50), Article e202413181. https://doi.org/10.1002/anie.202413181
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2024Copyright
© 2024 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH
Starting from N-acyl sulfonimidamides, mechanochemically generated rhodium nitrenoids undergo intramolecular N–O couplings to provide unprecedented 1,3,2,4-oxathiadiazole 3-oxides in good to excellent yields. The cyclization proceeds efficiently with a catalyst loading of only 0.5 mol% in the presence of phenyliodine(III) diacetate (PIDA) as oxidant. Neither an inert atmosphere nor additional heating is required in this solvent-free procedure. Under heat or blue light, the newly formed five-membered heterocycles function as nitrene precursors reacting with sulfoxides as exemplified by the imidation of dimethyl sulfoxide.
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S.P. and P.W. are grateful to the China Scholarship Council (CSC) for predoctoral stipends, and we acknowledge the Alexander von Humboldt Foundation for support of K.R. (AvHresearch award).License
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