A metal-free route to alkynyl sulfones under photoinduced conditions with the insertion of sulfur dioxide,Green Chemistry

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A metal-free route to alkynyl sulfones under photoinduced conditions with the insertion of sulfur dioxide
Green Chemistry ( IF 9.3 ) Pub Date : 2020/02/12 , DOI: 10.1039/d0gc00332h
Xinxing Gong _{1,

2,

3,

4} , Min Yang _{4,

5,

6,

7} , Jin-Biao Liu _{4,

7,

8,

9} , Fu-Sheng He _{1,

2,

3,

4} , Xiaona Fan _{4,

5,

6,

7} , Jie Wu _{1,

2,

3,

4,

10}

Affiliation

A metal-free route to alkynyl sulfones under photoinduced conditions is accomplished, starting from 4-alkyl Hantzsch esters, sulfur dioxide, and alkynyl bromides under visible light irradiation at room temperature. This transformation proceeds smoothly, affording the corresponding alkylalkynyl sulfones in moderate to good yields by using sodium metabisulfite as the sulfur dioxide surrogate. A plausible mechanism is proposed, showing that the alkyl radical generated in situ from 4-alkyl Hantzsch esters in the presence of a photocatalyst initiates the reaction. Subsequent sulfonylation, addition to alkynyl bromide, and release of bromide give rise to the corresponding alkylalkynyl sulfone.

中文翻译：

在光诱导条件下，通过插入二氧化硫而形成的无金属路线通往炔基砜

在室温下，在可见光照射下，从4-烷基Hantzsch酯，二氧化硫和炔基溴化物开始，在光诱导条件下实现了无金属路线生成炔基砜。通过使用偏亚硫酸氢钠作为二氧化硫替代物，该转化顺利进行，以中等至良好的产率提供了相应的烷基炔基砜。提出了一种可能的机理，表明在光催化剂存在下由4-烷基汉茨sch酯原位产生的烷基自由基引发了反应。随后的磺酰化，加到炔基溴化物中和释放出溴化物，产生相应的烷基炔基砜。

更新日期：2020-03-24

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