Highly Efficient and Selective Electrochemical Synthesis of Substituted Benzothiophenes and Benzofurans in Microcontinuous Flow,ACS Sustainable Chemistry & Engineering

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Highly Efficient and Selective Electrochemical Synthesis of Substituted Benzothiophenes and Benzofurans in Microcontinuous Flow
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2020-08-12 , DOI: 10.1021/acssuschemeng.0c03690
Dong Zhang ₁ , Jinlin Cai ₁ , Zheng Fang ₁ , Jinze Du ₁ , Xinxin Lin ₁ , Chengkou Liu ₁ , Wei He ₁ , Zhao Yang ₂ , Kai Guo _{1,

3}

Affiliation

A green and practical method for the synthesis of C-3 halogenated benzothiophenes and benzofurans from 2-alkynylthioanisoles or 2-alkynylanisoles and potassium halide was developed under transition-metal- and oxidant-free conditions, employing an assembled electrochemistry continuous-flow system. The carbon and platinum plates were used as the anode and cathode, respectively; KI or KBr not only served as a halogen source but also as an electrolyte. Moderate to good yields of C-3 halogenated benzothiophenes and benzofuran derivatives were obtained under constant current. Notably, the halogen could also be restored at the cathode to obtain C-3 dehalogenated benzothiophenes and benzofurans in high selectivity by adjusting the current and flow rate of the continuous-flow system. Moreover, this reaction could be easily scaled up with good efficiency in the continuous-flow system, which presents major advantages over reactions in a traditional batch.

中文翻译：

微连续流中高效选择性合成苯并噻吩和苯并呋喃的电化学合成

在无过渡金属和氧化剂的条件下，采用组装的电化学连续流系统，开发了一种绿色实用的方法，可从2-炔基硫代苯甲醚或2-炔基苯甲醚和卤化钾合成C-3卤代苯并噻吩和苯并呋喃。碳板和铂板分别用作阳极和阴极。KI或KBr不仅用作卤素源，而且用作电解质。在恒定电流下获得中等至良好产率的C-3卤代苯并噻吩和苯并呋喃衍生物。值得注意的是，还可以通过调节连续流系统的电流和流速，在阴极上还原卤素，从而以高选择性获得C-3脱卤的苯并噻吩和苯并呋喃。此外，

更新日期：2020-09-08

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