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

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.