Renaissance in Alkyne Semihydrogenation: Mechanism, Selectivity, Functional Group Tolerance, and Applications in Organic Synthesis

IF 51.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Chemical Reviews Pub Date : 2025-04-25 DOI:10.1021/acs.chemrev.4c00001

Rafał Kusy, Karol Grela

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Abstract

Alkenes constitute a significant class of chemical compounds with applications in the bulk, pharmaceutical, or perfume industry. Among the known methods of olefin production, semihydrogenation of the C–C triple bond seems to be the most straightforward one. Nonetheless, the success of this reaction requires full control over diastereoselectivity, eradication of a parasitic process of over-reduction or migration of the C–C double bond formed, and achieving satisfactory functional-group compatibility. The review demonstrates developments in the field of alkyne semihydrogenation over the period 2010–2022, with selected papers published in 2023 and 2024, emphasizing solutions to the above-mentioned limitations. We discuss mechanistic aspects of this transformation, including those related to unconventional systems. The review includes examples of applications of alkyne semihydrogenation in organic synthesis, confirming the considerable utility of this process. Finally, strategies to enhance catalyst selectivity are summarized. For the reader’s convenience, we provided a graphical guidebook to catalytic systems, illustrating the efficiency of the particular method.

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炔半氢化的复兴：机理、选择性、官能团耐受性及其在有机合成中的应用

烯烃是一类重要的化合物，在散装、制药或香水工业中都有应用。在已知的烯烃生产方法中，碳-碳三键的半氢化似乎是最直接的方法。然而，该反应的成功需要完全控制非对映选择性，消除形成的C-C双键的过度还原或迁移的寄生过程，并实现令人满意的官能团相容性。回顾了2010-2022年炔半氢化领域的发展，并选择了2023年和2024年发表的论文，重点介绍了上述限制的解决方案。我们讨论了这种转变的机制方面，包括那些与非常规系统相关的方面。综述了炔半氢化反应在有机合成中的应用实例，证实了该工艺的广泛应用。最后，总结了提高催化剂选择性的策略。为了方便读者，我们提供了催化系统的图解指南，说明了特定方法的效率。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Chemical Reviews 化学-化学综合

CiteScore

106.00

自引率

1.10%

发文量

278

审稿时长

4.3 months

期刊介绍： Chemical Reviews is a highly regarded and highest-ranked journal covering the general topic of chemistry. Its mission is to provide comprehensive, authoritative, critical, and readable reviews of important recent research in organic, inorganic, physical, analytical, theoretical, and biological chemistry. Since 1985, Chemical Reviews has also published periodic thematic issues that focus on a single theme or direction of emerging research.