Solvent Controlled Transformation between Sulfonyl Hydrazides and Alkynes: Divergent Synthesis of Benzo[b]thiophene‐1,1‐dioxides and (E)‐β‐iodo Vinylsulfones,Advanced Synthesis & Catalysis

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Solvent Controlled Transformation between Sulfonyl Hydrazides and Alkynes: Divergent Synthesis of Benzo[b]thiophene‐1,1‐dioxides and (E)‐β‐iodo Vinylsulfones
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2018-12-05 , DOI: 10.1002/adsc.201801258
Yue Ma ₁ , Kun Wang ₁ , Dong Zhang ₁ , Peng Sun ₁

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A green, efficient and controllable transformation between sulfonyl hydrazides and alkynes leading to benzo[b]thiophene‐1,1‐dioxides and (E)‐β‐iodo vinylsulfones via radical pathway has been developed. The reaction occurs rapidly in the presence of simply H₂O₂ and KI without the help of any transition metal. The chemoselectivity of the reaction is determined by the solvent in which the process is performed: TFE favors the cyclic product, while H₂O medium generates the iodosulfonylative product. Notably, this protocol also represents the first direct approach to the aggregation‐induced‐emmision (AIE) active benzo[b]thiophene‐1,1‐dioxides from readily available sulfonyl hydrazides and alkynes in one step.

中文翻译：

磺酰肼与炔烃之间的溶剂控制转化：苯并[b]噻吩-1,1-二氧化物和（E）-β-碘乙烯基砜的不同合成

已开发出一种绿色，高效且可控制的磺酰肼与炔烃之间通过自由基途径转化为苯并[ b ]噻吩-1,1-二氧化物和（E）-β-碘乙烯基砜的方法。在仅存在H ₂ O ₂和KI的情况下，无需任何过渡金属的帮助，该反应即可迅速发生。反应的化学选择性取决于在其中进行处理的溶剂：TFE有利于环状产物，而H ₂ O介质生成碘磺酰化产物。值得注意的是，该协议也是一步一步从易得的磺酰肼和炔烃中产生聚集诱导的发射（AIE）活性苯并[ b ]噻吩-1,1-二氧化物的第一种直接方法。

更新日期：2018-12-05

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