镍催化1,3-二烯的不对称氢官能团化反应研究进展

doi:10.6023/cjoc202403021

有机化学 ›› 2024, Vol. 44 ›› Issue (11): 3309-3320.DOI: 10.6023/cjoc202403021 上一篇下一篇

综述与进展

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)

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摘要/Abstract

1,3-二烯类化合物的区域选择性不对称氢官能团化反应是一种步骤及原子经济性地合成手性烯丙基或者高烯丙基化合物的方法, 在天然产物和生物活性分子的合成中有着重要的应用价值. 近年来, 丰产金属因其廉价易得、环境友好等优良特性在有机合成领域引起了广泛的关注. 本综述总结了近年来丰产金属镍催化的1,3-二烯与亲核试剂的不对称氢官能团化反应研究进展和现状, 对相关反应的底物范围、局限性以及反应机理进行了概述. 根据亲核试剂种类的不同, 主要包括不对称氢碳化反应、不对称氢胺化反应、不对称氢膦化反应以及不对称氢烷氧基化反应等.

关键词: 氢官能团化, 1,3-二烯, 不对称催化, 镍催化剂

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

引用此文

龙姣, 刘白雪, 张双双, 朱园园, 古双喜. 镍催化1,3-二烯的不对称氢官能团化反应研究进展[J]. 有机化学, 2024, 44(11): 3309-3320.

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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图/表 23

图式1. 1,3-二烯与亲核试剂的氢官能团化反应机理

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

图式2. 镍催化1,3-二烯的不对称氢官能团化反应(本综述框架)

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

图式3. 镍催化1,3-二烯与酮的对映选择性氢烷基化反应

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

图式4. 同位素标记实验及推测的机理

Scheme 4. Deuterium-labeling experiments and proposed mechanism

图式5. 镍催化非环支链1,3-二烯与酰胺或亚胺区域发散氢烷基化反应

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

图式6. 镍催化1,3-二烯的区域及对映选择性马氏氢单氟烷基化反应

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

图式7. 镍催化1,3-二烯的氢烯基化反应的典型机理

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

图式8. 镍催化1,3-二烯的对映选择性氢烯基化反应

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

图式9. 氢烯基化反应的应用

Scheme 9. Application of hydrovinylation reaction

图式10. 镍催化1,3-二烯与吲哚的不对称氢芳化反应

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

图式11. 同位素标记实验

Scheme 11. Deuterium-labeling experiment

图式12. 镍/铝双催化1,3-二烯与吡啶的不对称氢芳化反应

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

图式13. 镍催化1,3-二烯的不对称氢氰化反应

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

图式14. 镍催化1,3-二烯的不对称氢炔化反应

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

图式15. 镍催化支链1,3-二烯的不对称氢胺化反应

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

图式16. 镍催化直链1,3-二烯的不对称氢胺化反应

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

图式17. 推测的氢胺化反应机理

Scheme 17. Proposed mechanism of hydroamination

图式18. 镍催化1,3-二烯的不对称氢膦化反应

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

图式19. 推测的氢膦化反应机理

Scheme 19. Proposed mechanism of hydrophosphinylation

图式20. 镍催化支链1,3-二烯与苄醇的不对称氢烷氧基化反应

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

图式21. 镍催化1,3-丁二烯与乙醇的不对称氢烷氧基化反应

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

图式22. 镍催化1,3-二烯的不对称氢烷氧基化反应

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

图式23. 配体到配体的氢转移(LLHT)机理推测

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

参考文献 42

[1]	(a) Newhouse T.; Baran P. S.; Hoffmann R. W. Chem. Soc. Rev. 2009, 38, 3010. doi: 10.1039/b821200g pmid: 21378778
	(b) Noyori R. Nat. Chem. 2009, 1, 5. doi: 10.1038/nchem.143 pmid: 21378778
[2]	For selected reviews on hydrofunctionalization of alkenes, see: (a) Crossley S. W. M.; Obradors C.; Martinez R. M.; Shenvi R. A. Chem. Rev. 2016, 116, 8912. doi: 10.1021/acs.chemrev.6b00334 pmid: 27461578
	(b) Xiao L.-J.; Ye M.-C.; Zhou Q.-L. Synlett 2018, 30, 361. pmid: 27461578
	(c) Fernández D. F.; Mascareñas J. L.; López F. Chem. Soc. Rev. 2020, 49, 7378. pmid: 27461578
	(d) Liu R. Y.; Buchwald S. L. Acc. Chem. Res. 2020, 53, 1229. pmid: 27461578
	(e) Zhang W.; Wang Z.; Bai X.; Li B. Chin. J. Org. Chem. 2020, 40, 1087 (in Chinese). pmid: 27461578
	(张雯雯, 王紫璇, 白小燕, 李必杰, 有机化学, 2020, 40, 1087.) doi: 10.6023/cjoc202002017 pmid: 27461578
	(f) Biswas S.; Parsutkar M. M.; Jing S. M.; Pagar V. V.; Herbort J. H.; RajanBabu T. V. Acc. Chem. Res. 2021, 54, 4545. pmid: 27461578
	(g) Zhu S.; Tao R.; He Y. Synlett 2021, 33, 224. pmid: 27461578
	(h) He Y.; Chen J.; Jiang X.; Zhu S. Chin. J. Chem. 2022, 40, 651. pmid: 27461578
	(i) Zhang Z.; Bera S.; Fan C.; Hu X. J. Am. Chem. Soc. 2022, 144, 7015. pmid: 27461578
[3]	For selected reviews on hydrofunctionalization of alkynes, see: (a) Lalic G.; Suess A. Synlett 2016, 27, 1165. pmid: 36312376
	(b) Zheng Y.; Zi W. Tetrahedron Lett. 2018, 59, 2205. pmid: 36312376
	(c) Guo J.; Cheng Z.; Chen J.; Chen X.; Lu Z. Acc. Chem. Res. 2021, 54, 2701. pmid: 36312376
	(d) Nuñez Bahena E.; Schafer L. L. ACS Catal. 2022, 12, 14934. pmid: 36312376
	(e) Torres-Calis A.; García J. J. ACS Omega 2022, 7, 37008. doi: 10.1021/acsomega.2c05109 pmid: 36312376
[4]	For a selected review on hydrofunctionalization of allenes, see: Blieck R.; Taillefer M.; Monnier F. Chem. Rev. 2020, 120, 13545. doi: 10.1021/acs.chemrev.0c00803 pmid: 33301308
[5]	Perry G. J. P.; Jia T.; Procter D. J. ACS Catal. 2019, 10, 1485.
[6]	Adamson N. J.; Malcolmson S. J. ACS Catal. 2020, 10, 1060.
[7]	Flaget A.; Zhang C.; Mazet C. ACS Catal. 2022, 12, 15638.
[8]	Li G.; Huo X.; Jiang X.; Zhang W. Chem. Soc. Rev. 2020, 49, 2060.
[9]	Cheng Z.; Guo J.; Lu Z. Chem. Commun. 2020, 56, 2229.
[10]	For representative works on Rh-catalyzed asymmetric hydrofunctionalization of 1,3-dienes, see: (a) Roberts C. C.; Matías D. M.; Goldfogel M. J.; Meek S. J. J. Am. Chem. Soc. 2015, 137, 6488. pmid: 30155052
	(b) Goldfogel M. J.; Meek S. J. Chem. Sci. 2016, 7, 4079. doi: 10.1039/c5sc04908c pmid: 30155052
	(c) Marcum J. S.; Roberts C. C.; Manan R. S.; Cervarich T. N.; Meek S. J. J. Am. Chem. Soc. 2017, 139, 15580. pmid: 30155052
	(d) Yang X.-H.; Dong V. M. J. Am. Chem. Soc. 2017, 139, 1774. pmid: 30155052
	(e) Yang X.-H.; Davison R. T.; Dong V. M. J. Am. Chem. Soc. 2018, 140, 10443. pmid: 30155052
	(f) Yang X.-H.; Davison R. T.; Nie S.-Z.; Cruz F. A.; McGinnis T. M.; Dong V. M. J. Am. Chem. Soc. 2019, 141, 3006. pmid: 30155052
[11]	For representative works on Pd-catalyzed asymmetric hydrofunctionalization of 1,3-dienes, see: (a) O. Löber; M. Kawatsura; Hartwig J. F. J. Am. Chem. Soc. 2001, 123, 4366. pmid: 29446922
	(b) Adamson N. J.; Hull E.; Malcolmson S. J. J. Am. Chem. Soc. 2017, 139, 7180. doi: 10.1021/jacs.7b03480 pmid: 29446922
	(c) Adamson N. J.; Wilbur K. C. E.; Malcolmson S. J. J. Am. Chem. Soc. 2018, 140, 2761. doi: 10.1021/jacs.7b13300 pmid: 29446922
	(d) Park S.; Malcolmson S. J. ACS Catal. 2018, 8, 8468. pmid: 29446922
	(e) Park S.; Adamson N. J.; Malcolmson S. J. Chem. Sci. 2019, 10, 5176. pmid: 29446922
[12]	(a) Tasker S. Z.; Standley E. A.; Jamison T. F. Nature 2014, 509, 299.
	(b) Ananikov V. P. ACS Catal. 2015, 5, 1964.
[13]	(a) Clement N. D.; Routaboul L.; Grotevendt A.; Jackstell R.; Beller M. Chem. Eur. J. 2008, 14, 7408.
	(b) Behr A.; Becker M.; Beckmann T.; Johnen L.; Leschinski J.; Reyer S. Angew. Chem., Int. Ed. 2009, 48, 3598.
[14]	Wang Y.; Liu J.; He Z. Chin. J. Org. Chem. 2023, 43, 2614 (in Chinese).
	(王玉超, 刘晋彪, 何智涛, 有机化学, 2023, 43, 2614.) doi: 10.6023/cjoc202302010
[15]	Sato Y.; Saito N.; Mori M. J. Am. Chem. Soc. 2000, 122, 2371.
[16]	Yang Y.; Zhu S.-F.; Duan H.-F.; Zhou C.-Y.; Wang L.-X.; Zhou Q.-L. J. Am. Chem. Soc. 2007, 129, 2248. pmid: 17269780
[17]	Cheng L.; Li M.-M.; Xiao L.-J.; Xie J.-H.; Zhou Q.-L. J. Am. Chem. Soc. 2018, 140, 11627. doi: 10.1021/jacs.8b09346 pmid: 30183283
[18]	(a) Xiao L.-J.; Fu X.-N.; Zhou M.-J.; Xie J.-H.; Wang L.-X.; Xu X.-F.; Zhou Q.-L. J. Am. Chem. Soc. 2016, 138, 2957.
	(b) Xiao L. J.; Cheng L.; Feng W. M.; Li M. L.; Xie J. H.; Zhou Q. L. Angew. Chem., Int. Ed. 2017, 57, 461.
[19]	Shao W.; Besnard C.; Guénée L.; Mazet C. J. Am. Chem. Soc. 2020, 142, 16486. doi: 10.1021/jacs.0c08319 pmid: 32869987
[20]	Liao L.; Zhang Y.; Wu Z.-W.; Ye Z.-T.; Zhang X.-X.; Chen G.; Yu J.-S. Chem. Sci. 2022, 13, 12519.
[21]	Bogdanovic B.; Henc B.; Meister B.; Pauling H.; Wilke G. A. Angew. Chem., Int. Ed. 1972, 11, 1023.
[22]	Siv C.; Peiffer G.; Triantaphylides C.; Denis P.; Mortreux A.; Petit F.; Buono G. J. Org. Chem. 1985, 50, 1781.
[23]	Zhang A.; RajanBabu T. V. J. Am. Chem. Soc. 2006, 128, 54.
[24]	(a) Saha B.; Smith C. R.; RajanBabu T. V. J. Am. Chem. Soc. 2008, 130, 9000. pmid: 24961597
	(b) Shingate B. B.; Hazra B. G. Chem. Rev. 2014, 114, 6349. doi: 10.1021/cr4004083 pmid: 24961597
[25]	Cheng L.; Li M.-M.; Li M.-L.; Xiao L.-J.; Xie J.-H.; Zhou Q.-L. CCS Chem. 2022, 4, 2612.
[26]	Li J.-F.; Pan D.; Wang H.-R.; Zhang T.; Li Y.; Huang G.; Ye M. J. Am. Chem. Soc. 2022, 144, 18810.
[27]	Saha B.; RajanBabu T. V. Org. Lett. 2006, 8, 4657.
[28]	Yu R.; Xing Y.; Fang X. Org. Lett. 2021, 23, 930.
[29]	Shirakura M.; Suginome M. Angew. Chem., Int. Ed. 2010, 49, 3827.
[30]	Baker R.; Halliday D. E.; Smith T. N. J. Chem. Soc. D 1971, 23, 1583.
[31]	Pawlas J.; Nakao Y.; Kawatsura M.; Hartwig J. F. J. Am. Chem. Soc. 2002, 124, 3669. pmid: 11929257
[32]	Tran G.; Shao W.; Mazet C. J. Am. Chem. Soc. 2019, 141, 14814.
[33]	Long J.; Wang P.; Wang W.; Li Y.; Yin G. iScience 2019, 22, 369.
[34]	For selected reviews on hydrophosphinylation, see: (a) Xu Q.; Han L-B. J. Organomet. Chem. 2011, 696, 130.
	(b) Zhao D.; Wang R. Chem. Soc. Rev. 2012, 41, 2095.
	(c) Pullarkat S. Synthesis 2015, 48, 493.
	(d) Trofimov B.; Gusarova N.; Chernysheva N. Synthesis 2017, 49, 4783.
[35]	For representative works on transition metal-catalyzed hydrophosphinylation, see: (a) Nie S.-Z.; Davison R. T.; Dong V. M. J. Am. Chem. Soc. 2018, 140, 16450.
	(b) Lu Z.-W.; Zhang H.; Yang Z.; Ding N.; Meng L.; Wang J. ACS Catal. 2019, 9, 1457.
	(c) Dai Q.; Liu L.; Qian Y.; Li W.; Zhang J. Angew. Chem., Int. Ed. 2020, 59, 20645.
	(d) Yang Z.; Gu X.; Han L.-B.; Wang J. Chem. Sci. 2020, 11, 7451.
	(e) Duan S.; Pan A.; Du Y.; Zhu G.; Tian X.; Zhang H.; Walsh P. J.; Yang X. ACS Catal. 2023, 13, 10887.
[36]	Long J.; Li Y.; Zhao W.; Yin G. Chem. Sci. 2022, 13, 1390.
[37]	(a) González-Belman O.; Brotons-Rufes A.; Tomasini M.; Falivene L.; Caporaso L.; Jiménez-Halla J.; Poater A. Catalysts 2021, 11, 704.
	(b) Nanda S. K.; Mallik R. Chem. Eur. J. 2021, 27, 15571.
[38]	Kennemur J. L.; Maji R.; Scharf M. J.; List B. Chem. Rev. 2021, 121, 14649.
[39]	Tran G.; Mazet C. Org. Lett. 2019, 21, 9124.
[40]	Mifleur A.; Suisse I.; Mortreux A.; Sauthier M. Catal. Lett. 2021, 151, 27.
[41]	Li Q.; Wang Z.; Dong V. M.; Yang X.-H. J. Am. Chem. Soc. 2023, 145, 3909.
[42]	(a) Liu C.; Xie J.; Wu W.; Wang M.; Chen W.; Idres S. B.; Rong J.; Deng L.-W.; Khan S. A.; Wu J. Nat. Chem. 2021, 13, 451.
	(b) Feng K.; Chen J.; Gu S.; Wang H.; Chen F. Chin. J. Org. Chem. 2024, 44, 378 (in Chinese).
	(冯康博, 陈炯, 古双喜, 王海峰, 陈芬儿, 有机化学, 2024, 44, 378.) doi: 10.6023/cjoc202307005
	(c) Liu D.; Zhu Y.; Gu S.; Chen F. Chin. J. Org. Chem. 2021, 41, 1002 (in Chinese).
	(刘玎, 朱园园, 古双喜, 陈芬儿, 有机化学, 2021, 41, 1002.) doi: 10.6023/cjoc202007051

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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