Recent Advances in Nickel-Catalyzed Asymmetric Hydrofunctionalization of 1,3-Dienes

doi:10.6023/cjoc202403021

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (11): 3309-3320.DOI: 10.6023/cjoc202403021 Previous Articles Next Articles

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镍催化1,3-二烯的不对称氢官能团化反应研究进展

龙姣^a^,^c^,^*(), 刘白雪^a^,^c, 张双双^a^,^c, 朱园园^b, 古双喜^a^,^c^,^*()

a 武汉工程大学化工与制药学院绿色化工过程教育部重点实验室新型反应器与绿色化学工艺湖北省重点实验室武汉 430205
b 武汉工程大学化学与环境工程学院武汉 430205
c 武汉工程大学药物研究院武汉 430205

收稿日期:2024-03-15 修回日期:2024-06-05 发布日期:2024-06-24
基金资助:
国家自然科学基金(22377097); 湖北省自然科学基金(2021CFB556); 湖北省教育厅科学研究计划(Q20221513); 磷资源开发利用教育部工程研究中心开放基金(LCX202305)

Recent Advances in Nickel-Catalyzed Asymmetric Hydrofunctionalization of 1,3-Dienes

Jiao Long^a^,^c,*(), Baixue Liu^a^,^c, Shuangshuang Zhang^a^,^c, Yuanyuan Zhu^b, Shuangxi Gu^a^,^c,*()

a Key Laboratory for Green Chemical Process of Ministry of Education & Hubei Key Laboratory of Novel Reactor and Green Chemical Technology, School of Chemical Engineering and Pharmacy, Wuhan Institute of Technology, Wuhan 430205
b School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205
c Pharmaceutical Research Institute, Wuhan Institute of Technology, Wuhan 430205

Received:2024-03-15 Revised:2024-06-05 Published:2024-06-24
Contact: *E-mail:longjiao@wit.edu.cn;shuangxigu@163.com
Supported by:
National Natural Science Foundation of China(22377097); Natural Science Foundation of Hubei Province of China(2021CFB556); Science Research Foundation of Hubei Provincial Department of Education(Q20221513); Open Fund of Engineering Research Center of Phosphorus Resources Development and Utilization of Ministry of Education(LCX202305)

The regioselective asymmetric hydrofunctionalization of 1,3-dienes is a step- and atom-economic method for the synthesis of chiral allylic or homoallylic compounds, which has important application value in the synthesis of natural products and bioactive molecules. Over the years, earth-abundant transition metals have attracted extensive attention in the field of organic synthesis due to their excellent characteristics, such as affordability, accessibility, and environmental friendliness. In this review, the recent progress and status of asymmetric hydrofunctionalization of 1,3-dienes with different nucleophiles via nickel catalysis is summarized. The substrate scope, limitations and mechanism characteristics of related reactions are discussed. According to the different kinds of nucleophiles, it mainly includes asymmetric hydrocarbonation, asymmetric hydroamina- tion, asymmetric hydrophosphinylation and asymmetric hydroalkoxylation.

Key words: hydrofunctionalization, 1,3-dienes, asymmetric catalysis, nickel catalyst

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Jiao Long, Baixue Liu, Shuangshuang Zhang, Yuanyuan Zhu, Shuangxi Gu. Recent Advances in Nickel-Catalyzed Asymmetric Hydrofunctionalization of 1,3-Dienes[J]. Chinese Journal of Organic Chemistry, 2024, 44(11): 3309-3320.

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Fig. & Tab. 23

Scheme 1. Mechanism of hydrofunctionalization of 1,3-dienes with nucleophiles

Scheme 2. Nickel-catalyzed asymmetric hydrofunctionalization of 1,3-dienes (framework of this review)

Scheme 3. Ni-catalyzed enantioselective hydroalkylation of 1,3- dienes with ketones

Scheme 4. Deuterium-labeling experiments and proposed mechanism

Scheme 5. Ni-catalyzed regiodivergent hydroalkylation of acyclic branched dienes with amides or imides

Scheme 6. Ni-catalyzed regio- and enantioselective Markovnikov hydromonofluoroalkylation of 1,3-dienes

Scheme 7. Typical mechanism for Ni-catalyzed hydrovinylation of 1,3-dienes

Scheme 8. Ni-catalyzed enantioselective hydrovinylation of 1,3-dienes

Scheme 9. Application of hydrovinylation reaction

Scheme 10. Ni-catalyzed asymmetric hydroarylation of 1,3- dienes with indoles

Scheme 11. Deuterium-labeling experiment

Scheme 12. Ni/Al-dual-catalyzed asymmetric hydroarylation of 1,3-dienes with pyridine derivatives

Scheme 13. Ni-catalyzed asymmetric hydrocyanation of 1,3-dienes

Scheme 14. Ni-catalyzed asymmetric hydroalkynylation of 1,3- dienes

Scheme 15. Ni-catalyzed asymmetric hydroamination of branch 1,3-dienes

Scheme 16. Ni-catalyzed asymmetric hydroamination of linear 1,3-dienes

Scheme 17. Proposed mechanism of hydroamination

Scheme 18. Ni-catalyzed asymmetric hydrophosphinylation of 1,3-dienes

Scheme 19. Proposed mechanism of hydrophosphinylation

Scheme 20. Ni-catalyzed asymmetric hydroalkoxylation of branched dienes with benzyl alcohol

Scheme 21. Ni-catalyzed asymmetric hydroalkoxylation of butadiene with ethanol

Scheme 22. Ni-catalyzed asymmetric hydroalkoxylation of 1,3-dienes

Scheme 23. Proposed mechanism via ligand-to-ligand hydrogen transfer (LLHT)

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镍催化1,3-二烯的不对称氢官能团化反应研究进展

Recent Advances in Nickel-Catalyzed Asymmetric Hydrofunctionalization of 1,3-Dienes

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Fig. & Tab. 23

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