A metal-free visible-light-promoted phosphorylation/cyclization reaction in water towards 3-phosphorylated benzothiophenes,Organic Chemistry Frontiers

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A metal-free visible-light-promoted phosphorylation/cyclization reaction in water towards 3-phosphorylated benzothiophenes
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2020-06-17 , DOI: 10.1039/d0qo00222d
Xiao-Ya Yuan _{1,

2,

3,

4,

5} , Fan-Lin Zeng _{1,

2,

3,

4,

5} , Hu-Lin Zhu _{1,

2,

3,

4,

5} , Yan Liu _{1,

2,

3,

4,

5} , Qi-Yan Lv _{1,

2,

3,

4,

5} , Xiao-Lan Chen _{1,

2,

3,

4,

5} , Lifen Peng _{6,

7,

8,

9,

10} , Bing Yu _{1,

2,

3,

4,

5}

Affiliation

A metal-free visible-light-induced 2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile (4CzIPN)-catalyzed phosphorylation/cyclization reaction was developed in water at room temperature for the synthesis of 3-phosphorylated benzothiophenes. Notably, the conventional organic solvents were avoided. More importantly, this silver-free system circumvents the generation of by-product benzo[b]phosphole oxides. With this strategy, a series of 3-phosphorylated benzothiophenes bearing various functional groups were synthesized in good to excellent yields.

中文翻译：

水中无金属的可见光促进的磷酸化/环化反应，生成3-磷酸化的苯并噻吩

在室温下于水中开发了无金属的可见光诱导的2,4,5,6-四（9 H-咔唑-9-基）间苯二甲腈（4CzIPN）催化的磷酸化/环化反应，以合成3 -磷酸化的苯并噻吩。值得注意的是，避免了常规的有机溶剂。更重要的是，这种无银体系避免了副产物苯并[ b ]氧化物的生成。通过这种策略，合成了一系列带有各种官能团的3-磷酸化苯并噻吩，收率良好至极佳。

更新日期：2020-07-14

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