N‐Iodosuccinimide as Bifunctional Reagent in (E)‐Selective C(sp2)−H Sulfonylation of Styrenes,Asian Journal of Organic Chemistry

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N‐Iodosuccinimide as Bifunctional Reagent in (E)‐Selective C(sp2)−H Sulfonylation of Styrenes
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2018-12-04 , DOI: 10.1002/ajoc.201800644
Milan Pramanik ₁ , Khokan Choudhuri ₁ , Prasenjit Mal ₁

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Herein we report the use of N‐iodosuccinimide (NIS) as a bifunctional reagent for a regio‐ and (E)‐selective C(sp²)‐H sulfonylation reaction of styrenes. Styrenes and sulfonyl hydrazides treated with NIS and potassium carbonate in ethanol at 70 °C resulted in (E)‐vinyl sulfones exclusively with good to excellent yields. NIS, plays a dual role to generate sulfonyl radical from sulfonyl hydrazides at an initial stage and finally gives β‐iodosulfone intermediate which was further converted to (E)‐vinyl sulfones. Overall, a sustainable method for mild, metal free, convenient, one pot and direct synthesis of (E)‐vinyl sulfones from styrenes are demonstrated via a C−S coupling reaction.

中文翻译：

N-碘代琥珀酰亚胺在苯乙烯的（E）-选择性C（sp2）-H磺酰化中作为双功能试剂

本文中，我们报道了使用N-碘琥珀酰亚胺（NIS）作为双功能试剂进行苯乙烯的区域和（E）选择性C（sp ²）-H磺酰化反应。在70°C下用NIS和碳酸钾在乙醇中处理过的苯乙烯和磺酰肼生成（E）-乙烯基砜，其收率非常好。NIS起着双重作用，在初始阶段从磺酰肼生成磺酰基，最后得到β-碘砜中间体，该中间体进一步转化为（E）-乙烯基砜。总体而言，一种温和，无金属，方便，一锅直接合成（E的可持续方法苯乙烯-乙烯基砜通过C-S偶联反应得到证明。

更新日期：2018-12-04

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