Iron-catalyzed cross-electrophile coupling of bromostyrenes and chlorosilanes†

Ying Lin , Liang Zou , Renren Bai , Xiang-Yang Ye , Tian Xie , Yang Ye
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Abstract

We report here a facile and efficient vinylation method using Fe-catalyzed cross-electrophile coupling of readily available vinyl- and hydro-chlorosilanes with a variety of substituted alkenyl bromides using manganese as the terminal reductant. This C(sp2)–Si forming modular approach shows excellent functional group tolerance and broad substrate scope, which allows the creation of a series of vinyl organosilanes, including electron-rich, electron-poor, and ortho-/meta-/para-substituted vinyl electrophiles, which were coupled successfully. Moreover, several substrates with structurally complex natural products and pharmaceutical motifs were well modified by this vinyl silylation process. Gram-scale reaction and derivatization of the formed vinyl organosilanes are demonstrated.

Abstract Image

铁催化的溴苯乙烯与氯硅烷的交叉亲电偶联
我们在此报道了一种简单有效的乙烯基化方法,该方法使用铁催化易得的乙烯基和氢氯硅烷与各种取代的烯基溴化物的亲电偶联,使用锰作为末端还原剂。这种形成C(sp2)–Si的模块化方法显示出优异的官能团耐受性和广阔的衬底范围,这允许产生一系列乙烯基有机硅烷,包括富电子、贫电子和邻位/间位/对位取代的乙烯基亲电试剂,并成功偶联。此外,几种具有结构复杂的天然产物和药物基序的底物通过这种乙烯基硅烷化过程得到了很好的改性。演示了所形成的乙烯基有机硅烷的革兰氏规模反应和衍生化。
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CiteScore
7.80
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