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Synlett 2023; 34(19): 2262-2292
DOI: 10.1055/a-2068-6215
DOI: 10.1055/a-2068-6215
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Cross-Coupling Reactions between Alkenes by C–H Cyclometalation
We gratefully acknowledge the National Natural Science Foundation of China (NSFC) (22278103 and 21502037), the Natural Science Foundation of Zhejiang Province (ZJNSF) (LY19B020006 and LY15B020008), the Key Subject of Stomatology in Hangzhou, Hangzhou Normal University, National Key R&D Program of China (2018YFA0702400), and Sinopec Technology (P22015) for financial support.
Abstract
Alkenes are one of the most abundant raw feedstocks and are utilized to construct complex chemicals, whilst cross-coupling reactions using alkenes represents a powerful method toward valuable chemicals. In the past decade, cross-coupling reactions of simple alkenes by chelation-assisted alkenyl C–H functionalization has attracted significant attention due to its atom/step efficiency and excellent Z/E selectivity, proceeding by C–H exo-cyclometalation and endo-cyclometalation. In this account, we summarize transition-metal-catalyzed cross-coupling reactions between alkenes to generate 1,3-dienes via C–H alkenylation,1,4-dienes through C–H allylation, multisubstituted alkenes via hydroalkenylation, and heterocycles by way of tandem alkenyl C–H functionalization/annulation. Asymmetric alkenyl C–H alkenylation to prepare axially chiral aryl 1,3-dienes is also discussed.
1 Introduction
2 Alkenyl C–H Alkenylation
2.1 By endo-Cyclometalation
2.2 By exo-Cyclometalation
3 Alkenyl C–H Allylation
3.1 By endo-Cyclometalation
3.2 By exo-Cyclometalation
4 Alkenyl C–H Alkylation via Hydroalkenylation
5 Cascade Reactions
6 Conclusion
Key words
alkenes - C–H functionalization - cross-coupling - chelation assistance - transition-metal catalysisPublication History
Received: 14 March 2023
Accepted after revision: 04 April 2023
Accepted Manuscript online:
04 April 2023
Article published online:
24 May 2023
© 2023. Thieme. All rights reserved
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