Recent Advances in Copper-Catalyzed Boron-Reagent-Involved Multicomponent Difunctionalization of Alkenes

doi:10.6023/cjoc202012010

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (6): 2280-2289.DOI: 10.6023/cjoc202012010 Previous Articles Next Articles

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铜催化硼试剂参与的烯烃多组分双官能化研究进展

杨晨, 贾雪锋^*()

山西师范大学化学与材料科学学院磁性分子与磁信息材料教育部重点实验室山西临汾 041000

收稿日期:2020-12-04 修回日期:2021-01-18 发布日期:2021-02-22
通讯作者: 贾雪锋
基金资助:
山西省自然科学基金(201901D111276)

Recent Advances in Copper-Catalyzed Boron-Reagent-Involved Multicomponent Difunctionalization of Alkenes

Chen Yang, Xuefeng Jia()

Key Laboratory of Magnetic Molecules & Magnetic Information Materials (Ministry of Education), School of Chemistry and Material Science, Shanxi Normal University, Linfen, Shanxi 041000

Received:2020-12-04 Revised:2021-01-18 Published:2021-02-22
Contact: Xuefeng Jia
Supported by:
Natural Science Foundation of Shanxi Province(201901D111276)

The multicomponent difunctionalization of alkenes is an important and highly efficient reaction for the rapid construction of molecules with structure diversity, which has some advantanges of high atom economy, wide substrate range as well as mild conditions and becomes the main research hotspot in organic synthesis in recent years. Many examples on the multicomponent difunctionalization of alkenes under metal-catalyzed or metal-free conditions have extentively been reported. Among them, the asymmetric version of some reactions was successfully achieved by the use of chiral ligands. However, compared with nobel metal catalysts such as ruthenium, rhodium, iridium, palladium and silver, the cheaper metal catalysts including iron, cobalt, nickel, copper, manganese have attracted more special attention. In view of the application of copper catalyst and organoboron reagents in organic synthesis, the advances in copper-catalyzed multicomponent difunctionalization of alkenes with organoboron reagents since 2018 are reviewed. The major challenges and development prospects of this fields, including the discovery of new reaction type and organoboron reagents, better stereoselectivity, and deeper understanding on reaction mechanism are also discussed.

Key words: copper-catalysis, boron reagent, alkene, multicomponent difunctionalization

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Chen Yang, Xuefeng Jia. Recent Advances in Copper-Catalyzed Boron-Reagent-Involved Multicomponent Difunctionalization of Alkenes[J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2280-2289.

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Fig. & Tab. 10

Scheme 1. Reaction pattern on copper-catalyzed multicomponent difunctionalization of alkenes with organoboron reagents

Scheme 2. Copper-catalyzed asymmetric aminoboration of alkyl-substituted alkenes

Scheme 3. Catalyst-controlled 1,1- and 1,2-arylboration of α-alkyl alkenyl arenes

Scheme 4. Copper- and palladium-cocatalyzed stereospecific arylboration of alkenyl-Bdan compounds

Scheme 5. Copper-catalyzed borylative heteroarylation of vinylarenes and proposed catalytic cycle

Scheme 6. Copper and palladium cooperative catalyzed four-component borocarbonylation of vinylarenes

Scheme 7. Mechanism of copper and palladium cooperative catalyzed four-component borocarbonylation of vinylarenes

Scheme 8. Proposed mechanism of copper-catalyzed cyclopropanation of aliphatic alkenes

Scheme 9. Copper-catalyzed reagent-controlled regioselective cyanoborylation of vinylarenes

Scheme 10. Mechanism of copper-catalyzed arylsulfonylation of styrenes via radical relay pathway

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铜催化硼试剂参与的烯烃多组分双官能化研究进展

Recent Advances in Copper-Catalyzed Boron-Reagent-Involved Multicomponent Difunctionalization of Alkenes

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