"Green" Oxidant (Oxygen) Mediated Synthesis of N-(2-(Methylsulfonyl)ethyl)amide Derivatives Using DMSO as a Dual Synthon and Solvent.

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-10-01 DOI:10.1021/acs.orglett.5c03851

Yongfa Xie,Changlong Zhuo,Siming Gong,Hui Wu,Hu Cai

引用次数: 0

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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“绿色”氧化剂（氧）介导合成N-（2-（甲基磺酰基）乙基）酰胺衍生物的DMSO作为双合成物和溶剂。

砜衍生物是许多药物的重要组成部分。本文报道了一种利用环境无害的氧化剂（氧）合成N-（2-（甲基磺酰基）乙基）酰胺化合物和酰胺化合物和二甲亚砜（DMSO）的砜骨架的有效方法。该无金属协议具有操作简单，低成本和无害的氧化介质，良好的官能团耐受性和可扩展性到克级的特点。值得注意的是，DMSO作为双合成供体，在作为溶剂的同时提供亚甲基（- ch2 -）和甲基磺酰基（- so2me）形成C(sp3)- n和C(sp3)-C（sp3）键。基于控制实验和EPR光谱分析，提出了一种自由基机理。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.