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Updated: Jan 16, 2026
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
"Green" Oxidant (Oxygen) Mediated Synthesis of N-(2-(Methylsulfonyl)ethyl)amide Derivatives Using DMSO as a Dual
Yongfa Xie1, Changlong Zhuo1, Siming Gong1
1School of Chemistry and Chemical Engineering, Nanchang University, Nanchang 330031, China.
Abstract:
Sulfone derivatives are important components of many pharmaceuticals. This Letter reports an efficient method for synthesizing N-(2-(methylsulfonyl)ethyl)amide compounds with sulfone skeletons from amide compounds and dimethyl sulfoxide (DMSO) using an environmentally benign oxidant (oxygen). This metal-free protocol features operational simplicity, a low-cost and nonhazardous oxidant mediator, good functional group tolerance, and scalability to gram-scale. Notably, DMSO acts as a dual synthon donor, providing both methylene (-CH2-) and methylsulfonyl (-SO2Me) groups to form C(sp3)-N and C(sp3)-C(sp3) bonds while serving as the solvent. A radical mechanism is proposed based on control experiments and EPR spectroscopy.
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