Synlett 2023; 34(19): 2262-2292
Cross-Coupling Reactions between Alkenes by C–H Cyclometalation
Xi Lu
a
Research 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
b
College 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∗
b
College 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∗
b
College 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
› Institutsangaben 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 catalysis
Publikationsverlauf
Eingereicht: 14. März 2023
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
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