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Synthesis 2023; 55(24): 4062-4079
DOI: 10.1055/a-2124-3903
DOI: 10.1055/a-2124-3903
short review
Palladium-Catalyzed Homo-Dimerization of Terminal Alkynes
The authors are grateful to the National Natural Science Foundation of China (22172014, 22062012 and 22262019), the Natural Science Foundation of Guizhou Province (qiankehejichu-ZK [2023]zhongdian048), and the Foundation of Guizhou Educational Committee (qianjiaoji [2023] 088) for financial support. This work was also supported by the Liaoning Revitalization Talents Program (XLYC1802030) and the Natural Science Foundation of Liaoning, China (2019JH3/30100001).
Abstract
The palladium-catalyzed homo-dimerization of terminal alkynes is a powerful and atom-economic method for the preparation of highly unsaturated four-carbon skeletons, which are key structural units found in natural and/or biologically active products and materials. However, during the homo-dimerization of terminal alkynes, a major issue is control of the chemo-, regio-, and stereoselectivity. Thus, over the past few decades, various strategies and methods have been developed that employ palladium catalytic systems for such homo-dimerizations. In this Short Review, we highlight important methods for the selective synthesis of these valuable four-carbon compounds, including conjugated 1,3-enynes, 1,3-diynes, and 1,3-dienes.
1 Introduction
2 Redox-Neutral Homo-Dimerization of Terminal Alkynes for the Synthesis of 1,3-Enynes
2.1 Head-to-Head Dimerization
2.2 Head-to-Tail Dimerization
3 Oxidative Homo-Dimerization of Terminal Alkynes for the Synthesis of 1,3-Diynes
3.1 Unsupported Palladium Catalysts
3.1.1 Choice of Oxidant
3.1.2 Choice of Ligand
3.1.3 Choice of Solvent
3.2 Supported Palladium Catalysts
4 Reductive Homo-Dimerization of Terminal Alkynes for the Synthesis of 1,3-Dienes
5 Conclusion
Key words
homo-dimerization - terminal alkynes - palladium catalysis - unsaturated four-carbon skeletons - selectivityPublication History
Received: 07 June 2023
Accepted after revision: 06 July 2023
Accepted Manuscript online:
06 July 2023
Article published online:
16 August 2023
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