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首页> 外文期刊>Angewandte Chemie >Catalytic Stereoselective Semihydrogenatioe of Alkynes to E-Alkenes
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Catalytic Stereoselective Semihydrogenatioe of Alkynes to E-Alkenes

机译：炔烃催化立体选择性半氢化为电子烯烃

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摘要

Installing the alkyne functionality as a synthetic precursor to Z-configured carbon-carbon double bonds through syn-selective semihydrogenation is a common approach in organic synthesis. Many mild, functional-group-tolerant, and high-yielding catalytic (homogeneous and heterogeneous) and noncatalytic methods exist, with the Lindlar protocol being the most popular choice. However, the analogous direct reduction of the alkyne functionality to the E-configured alkene is a transformation that remains a major challenge, particularly in late-stage synthesis. The textbook example of Birch-type reduction using NH3 or amines and noncatalytic dissolving metals does indeed provide good E-selectivities, however, functional-group intolerance is a major limitation owing to the aggressive nature of the reaction conditions. Although some improvement in the scope of the ii-selective hydrogenation reaction has been achieved through the use of overstoichiometric amounts of chromium reagents,''*' the use of noncatalytic, toxic reagents is not ideal. Herein, we focus on the significant advancements made in recent years toward the development of an E-selective, catalytic, functional-group-tolerant semihydrogenation of alkynes through transition-metal catalysis.
机译：通过合成选择性半氢化法将炔烃官能团安装为Z-构型的碳-碳双键的合成前体是有机合成中的常见方法。存在许多温和，耐功能基团和​​高产率的催化（均相和异相）和非催化方法，其中Lindlar协议是最受欢迎的选择。然而，将炔烃官能团直接还原成E-构型烯烃是仍然是主要挑战的转化，特别是在后期合成中。使用NH3或胺和非催化溶解性金属进行桦木型还原的教科书实例确实提供了良好的E选择性，但是，由于反应条件的攻击性，官能团不耐受性是一个主要限制。尽管通过使用化学计量过量的铬试剂已实现了ii-选择性氢化反应范围的一些改进，但使用非催化的有毒试剂并不是理想的选择。本文中，我们重点介绍近年来通过过渡金属催化在炔烃的E选择性，催化，官能团耐受的半氢化反应方面取得的重大进展。

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