Cross-Coupling Reactions between Alkenes by C–H Cyclometalation

Xi Lu; Yini Wang; Kailin Xie; Jian Zhang

doi:10.1055/a-2068-6215

Synlett, Table of Contents

Synlett 2023; 34(19): 2262-2292
DOI: 10.1055/a-2068-6215

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Cross-Coupling Reactions between Alkenes by C–H Cyclometalation

Xi Lu

^aResearch Institute of Petroleum Exploration and Development of Sinopec, Baisha Road No.5 of Shahe Town, Changping County, Beijing, 102200, P. R. of China

,

Yini Wang

^bCollege of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou, 311121 Zhejiang, P. R. of China

,

Kailin Xie∗

^bCollege of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou, 311121 Zhejiang, P. R. of China

,

Jian Zhang∗

^bCollege of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou, 311121 Zhejiang, P. R. of China

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Abstract

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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 catalysis

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References

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