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Published on: May 21, 2019
Radical Sulfimidation via Visible-Light Photoredox Catalysis: N-Acyloxyamides as Bench-Stable Nitrene Surrogates
Shuangqing Li1, S Mohammad Amen1, Kelin Chen1
1College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, China.
Abstract:
Herein, we describe a visible-light-driven sulfimidation of thioethers with N-acyloxyamides catalyzed by TPT. The protocol proceeds under ambient conditions, tolerates a broad range of functional groups, and delivers the desired products in yields of up to 99%. The gram-scale reaction retains full efficiency with 1 mol % catalyst loading. Products such as N-allyl-N-(thio)amides, N-sulfonyl sulfimides, and N-acyl sulfoximines could be readily afforded with the methodology. Preliminary mechanistic investigations suggest that a radical cross-coupling pathway might be involved.
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