Visible‐Light‐Induced Radical Cascade Cyclizations of 1,7‐Enynes with Sulfinic Acids: Direct Access to Sulfonated Chromanes and Sulfonated Tetrahydroquinolines under Metal‐Free Conditions,Advanced Synthesis & Catalysis

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Visible‐Light‐Induced Radical Cascade Cyclizations of 1,7‐Enynes with Sulfinic Acids: Direct Access to Sulfonated Chromanes and Sulfonated Tetrahydroquinolines under Metal‐Free Conditions
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-10-09 , DOI: 10.1002/adsc.202000846
Qi Liu _{1,

2} , Yousheng Mei ₂ , Lei Wang _{1,

2,

3} , Yongmin Ma _{1,

3} , Pinhua Li _{2,

3}

Affiliation

Visible‐light‐induced strategy to access sulfonated chromanes and sulfonated 1,2,3,4‐tetrahydroquinolines via a radical cascade cyclization of 1‐(arylethynyl)‐2‐(vinyloxy)benzenes and N‐allyl‐2‐(arylethynyl)anilines with aromatic and aliphatic sulfinic acids has been developed. In the presence of TBHP (7.5 mol%) as an oxidant and Eosin Y (3.0 mol%) as a photocatalyst, the reactions undergo smoothly to afford the corresponding products in good yields at room temperature under metal‐free conditions. This transformation features low loading of TBHP, mild reaction conditions, simple operation, broad functional‐group tolerance, and good yields of products.

中文翻译：

1,7-炔烃与亚磺酸的可见光诱导的自由基级联环化：无金属条件下直接接触磺化色氨酸和磺化四氢喹啉

可见光诱导策略通过1-（芳基乙炔基）-2-（乙烯基氧基）苯和N-烯丙基-2-（芳基乙炔基）苯胺的自由基级联环化反应来获得磺化的苯并二氢吡喃和磺化的1,2,3,4-四氢喹啉已经开发出具有芳族和脂族亚磺酸的化合物。在TBHP（7.5 mol％）作为氧化剂和曙红Y（3.0 mol％）作为光催化剂的情况下，反应平稳进行，从而在室温下无金属条件下以高收率得到相应的产物。这种转变的特点是TBHP的负载量低，反应条件温和，操作简单，对官能团的耐受性强以及产品收率高。

更新日期：2020-10-09

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