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首页> 外文期刊>Chemistry: A European journal >An Alkene-Promoted Borane-Catalyzed Highly Stereoselective Hydrogenation of Alkynes to Give Z- and E-Alkenes
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An Alkene-Promoted Borane-Catalyzed Highly Stereoselective Hydrogenation of Alkynes to Give Z- and E-Alkenes

机译：烯烃促进的硼烷催化的炔烃高度立体选择性加氢，生成Z和E烯烃

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摘要

The stereoselective hydrogenation of alkynes to alkenes is an extremely useful transformation in synthetic chemistry. Despite numerous reports for the synthesis of Z-alkenes, the hydrogenation of alkynes to give E-alkenes is still not well resolved. In particular, selective preparation of both Z- and E-alkenes by the same catalytic hydrogenation system using molecular H-2 has rarely been reported. In this paper, a novel strategy of using simple alkenes as promoters for the HB(C6F5)(2)- catalyzed metal-free hydrogenation of alkynes was adopted. Significantly, both Z- and E-alkenes can be furnished by hydrogenation with molecular H-2 in high yields with excellent stereoselectivities. Further experimental and theoretical mechanistic studies suggest that interactions between H and F atoms of the alkene promoter, borane intermediate, and H-2 play an essential role in promoting the hydrogenolysis reaction.
机译：炔烃立体选择性加氢为烯烃是合成化学中极为有用的转变。尽管有许多关于Z-烯烃合成的报道，但炔烃加氢生成E-烯烃的方法仍然没有很好地解决。特别是，很少有人报道使用分子H-2通过相同的催化氢化系统选择性地制备Z-和E-烯烃。在本文中，采用了一种新的策略，即使用简单的烯烃作为促进剂，用于HB（C6F5）（2）催化的炔烃的无金属氢化。重要的是，Z-和E-烯烃都可以通过分子H-2的氢化以高产率提供，且具有出色的立体选择性。进一步的实验和理论机理研究表明，烯烃促进剂，硼烷中间体和H-2的H和F原子之间的相互作用在促进氢解反应中起着至关重要的作用。

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