Issue 3, 2022

Hydroelementation of diynes


This review highlights the hydroelementation reactions of conjugated and separated diynes, which depending on the process conditions, catalytic system, as well as the type of reagents, leads to the formation of various products: enynes, dienes, allenes, polymers, or cyclic compounds. The presence of two triple bonds in the diyne structure makes these compounds important reagents but selective product formation is often difficult owing to problems associated with maintaining appropriate reaction regio- and stereoselectivity. Herein we review this topic to gain knowledge on the reactivity of diynes and to systematise the range of information relating to their use in hydroelementation reactions. The review is divided according to the addition of the E–H (E = Mg, B, Al, Si, Ge, Sn, N, P, O, S, Se, Te) bond to the triple bond(s) in the diyne, as well as to the type of the reagent used, and the product formed. Not only are the hydroelementation reactions comprehensively discussed, but the synthetic potential of the obtained products is also presented. The majority of published research is included within this review, illustrating the potential as well as limitations of these processes, with the intent to showcase the power of these transformations and the obtained products in synthesis and materials chemistry.

Graphical abstract: Hydroelementation of diynes

Article information

Article type
Review Article
26 Oct 2021
First published
10 Jan 2022
This article is Open Access
Creative Commons BY license

Chem. Soc. Rev., 2022,51, 869-994

Hydroelementation of diynes

J. Walkowiak, J. Szyling, A. Franczyk and R. L. Melen, Chem. Soc. Rev., 2022, 51, 869 DOI: 10.1039/D1CS00485A

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