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首页> 外文期刊>Chemistry: A European journal >Copper-catalyzed three-component borylstannylation of alkynes
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Copper-catalyzed three-component borylstannylation of alkynes

机译：铜催化炔烃的三组分硼烷基锡烷基化

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摘要

Regio- and stereoselective installation of boryl and stannyl moieties into a carbon-carbon triple bond of various alkynes has been achieved based on a three-component coupling reaction by using a diboron and a tin alkoxide with the aid of a copper(II) acetate-tricyclohexylphosphine complex, giving diverse vic-borylstannylalkenes in a straightforward manner. Carbon-tin and carbon-boron bonds of the resulting borylstannylation product are successively transformed into carbon-carbon bonds by a Migita-Kosugi-Stille and a Suzuki-Miyaura coupling, leading to the formation of (Z)-tamoxifen with anti-breast cancer activity. Borylstannylation: A copper-tricyclohexylphosphine complex was found to catalyse the three-component borylstannylation of alkynes with a diboron and a tin alkoxide to afford vic-borylstannylalkenes in a regio- and stereoselective manner. Synthetic utility of the resulting borylstannylation product was demonstrated by a three-step synthesis of (Z)-tamoxifen from commercially available substrates by successive Migita-Kosugi-Stille and Suzuki-Miyaura couplings (see scheme).
机译：在三组分偶联反应的基础上，通过使用乙硼烷和锡醇盐，借助乙酸铜（II），将硼烷基和苯乙烯基部分区域选择性和立体选择性地安装到各种炔烃的碳-碳三键中。三环己基膦配合物，可以直接生成多种vic-硼烷基锡烷基。通过Migita-Kosugi-Stille和Suzuki-Miyaura偶联将所得的硼烷基锡烷基化产物的碳-锡和碳-硼键相继转化为碳-碳键，从而导致形成具有抗乳腺癌作用的（Z）-他莫昔芬活动。硼烷基锡烷基化：发现铜-三环己基膦配合物可催化乙炔与三硼烷和锡醇盐的三组分硼烷基锡烷基化，从而以区域和立体选择性的方式提供vic-硼烷基锡烷基烯烃。通过连续的Migita-Kosugi-Stille和Suzuki-Miyaura偶联从商业上可获得的底物进行三步合成（Z）-他莫昔芬，证明了所生成的硼烷基甲锡烷基化产物的合成效用（参见方案）。

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