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2023 , Vol. 43 >Issue 2: 455 - 470

DOI: https://doi.org/10.6023/cjoc202208008

综述与进展

无过渡金属催化的Suzuki-Type交叉偶联反应研究进展

  • 马彪 ,
  • 章淼淼 ,
  • 李占宇 ,
  • 彭进松 ,
  • 陈春霞
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  • a 东北林业大学化学化工与资源利用学院 哈尔滨 150040
    b 东北林业大学林业工程博士后流动站 哈尔滨 150040

收稿日期: 2022-08-06

  修回日期: 2022-09-25

  网络出版日期: 2022-11-01

基金资助

中央高校基本科研业务费专项资金基金(2572020BU03); 中国博士后科学基金(2020M681065); 黑龙江省博士后基金(LBH-Z20103)

收起

Recent Advance of Transition Metal-Free Catalyzed Suzuki-Type Cross Coupling Reaction

  • Biao Ma ,
  • Miaomiao Zhang ,
  • Zhanyu Li ,
  • Jinsong Peng ,
  • Chunxia Chen
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  • a Chemical Engineering and Resource Utilization, College of Chemistry, Northeast Forestry University, Harbin 150040
    b Material Science and Engineering College, Northeast Forestry University, Harbin 150040
* Corresponding authors. E-mail: ;

Received date: 2022-08-06

  Revised date: 2022-09-25

  Online published: 2022-11-01

Supported by

Fundamental Research Funds for the Central Universities(2572020BU03); China Postdoctoral Science Foundation Funded Project(2020M681065); Heilongjiang Postdoctoral Fund(LBH-Z20103)

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摘要

过渡金属催化的Suzuki交叉偶联反应是构建碳碳键最高效和最广泛的方法之一, 其广泛的研究极大地推动了合成化学的发展. 当前Suzuki交叉偶联反应主要依赖于贵金属钯催化体系, 然而, 金属钯储量低、价格昂贵及高毒性等弊端已经严重地限制了其在现代合成中的发展. 在过去二十年时间, 无金属催化的Suzuki-Type交叉偶联反应受到了广泛的关注, 许多新型高效的反应体系被开发报道. 总结了近二十年无金属催化的Suzuki-Type交叉偶联反应的研究进展, 主要涉及的反应类型包括碱、金属有机试剂和有机小分子促进的反应, 并对相关的反应机理进行了阐述.

关键词： 无金属催化; Suzuki交叉偶联; 有机合成; 碱促进; 偶联反应

本文引用格式

马彪 , 章淼淼 , 李占宇 , 彭进松 , 陈春霞 . 无过渡金属催化的Suzuki-Type交叉偶联反应研究进展[J]. 有机化学, 2023 , 43(2) : 455 -470 . DOI: 10.6023/cjoc202208008

Abstract

Transition metal catalyzed Suzuki coupling reaction serves as one of the most versatile and widespread methods for the C-C bonds formation, which greatly promotes the development of synthetic chemistry. Currently, the Suzuki coupling reactions heavily rely on noble palladium-catalyzed system. However, the high cost, toxicity and low reserves of palladium have become the main obstacles for their development in organic synthesis. Over the past two decades, metal-free catalyzed Suzuki-Type cross coupling reactions earned extensive concern, and a large number of efficient and new reaction systems have been reported. In this review, the recent progresses of metal-free catalyzed Suzuki-Type cross coupling reactions are summarized, mainly including bases, organometallic reagents and organic molecules promoted reactions. In addition, the mechanism of reaction is also discussed in this review.

Key words： metal-free catalysis; Suzuki cross-coupling; organic synthesis; base promoting; coupling reaction

参考文献

[1]
(a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
[1]
(b) Patel, K. N.; Bedekar. A. V. Catal. Lett. 2015, 145, 1710
[1]
(c) Zhang, L.; Yang, C.; Guo, X.-F.; Mo, F.-Y. Chin. J. Org. Chem. 2021, 41, 3492. (in Chinese)
[1]
(张雷, 杨晨, 郭雪峰, 莫凡洋, 有机化学, 2021, 41, 3492.)
[2]
Schneider, N.; Lowe, D. M.; Sayle, R, A.; Tarselli, M.; Landrum, G. J. Med. Chem. 2016, 59, 4385.
[3]
Li, Y.; Duan, G. T.; Liu, G. Q.; Cai, W. P. Chem. Soc. Rev. 2013, 42, 3614.
[4]
Adamo, C.; Amatore, C.; Ciofini, I.; Jutand, A.; Lakmini, H. J. Am. Chem. Soc. 2006, 128, 6829.
[5]
(a) Narayan, S.; Muldoon, J.; Finn, M.; Fokin, V.; Kolb, H.; Sharpless, K. J. Angew. Chem. Int. Ed. 2005, 44, 21.
[5]
(b) Kambe, N.; Iwasaki, T.; Terao, J. Chem. Soc. Rev. 2011, 40, 4937
[5]
(c) Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature 2014, 509, 299.
[6]
Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417.
[7]
Felpin, F. X.; Ayad, T.; Mitra, S. Eur. J. Org. Chem. 2006, 2679.
[8]
(a) Bedford, R. B.; Brenner, P. B.; Carter, E.; Carvell, T. W; Cogswell, P. M.; Gallagher, T.; Harvey, J. N.; Murphy, D. M.; Neeve, E. C.; Nunn, J.; Pye, D. M. Chem.-Eur. J. 2014, 20, 7935.
[8]
(b) Hashimoto, T.; Hatakeyama, T.; Nakamura, M. J. Org. Chem. 2012, 77, 1168
[8]
(c) Hatakeyama, T.; Hashimoto, T.; Kathriarachchi, K. K. A. D. S.; Zenmyo, T.; Seike, H.; Nakamura, M. Angew. Chem. 2012, 124, 8964.
[9]
Neely, J. A.; Bezdek, M. J.; Chirik, P. J. ACS Cent. Sci. 2016, 2, 12.
[10]
(a) Shields, J. D.; Gray, E. E.; Doyle, A. G. Org. Lett. 2015, 17, 2166.
[10]
(b) Mastalir, M.; Sto?ger, B.; Pittenauer, E.; Allmaier, G.; Kirchner, K. Org. Lett. 2016, 18, 3186
[10]
(c) Shi, S.; Meng, G.; Szostak, M. Angew. Chem., Int. Ed. 2016, 55, 6959.
[10]
(d) Shi, S.; Meng, G.; Szostak, M. Angew. Chem., Int. Ed. 2016, 55, 6959.
[10]
(e) Chen, G.-J.; Du, J.-S. Chin. J. Org. Chem. 2014, 34, 65. (in Chinese)
[10]
(陈国军, 杜建时, 有机化学, 2014, 34, 65.)
[10]
(f) Li, Y.-Q.; Fan, Y.-H.; Jia, Q.-F. Chin. J. Org. Chem. 2019, 39, 350. (in Chinese)
[10]
(李娅琼, 范玉航, 贾乾发, 有机化学, 2019, 39, 350.)
[11]
(a) Basnet, P.; Thapa, S.; Dickie, D. A.; Giri, R. Chem. commun. 2016, 52, 11072.
[11]
(b) Sun, Y.; Yi, J.; Lu, X.; Zhang, Z.; Xiao, B.; Fu, Y. Chem. Commun. 2014, 50, 11060
[11]
(c) Zhou, Y. Q.; You, W.; Smith, K. B.; Brown, K. M. Angew. Chem. 2014, 126, 3543.
[12]
Leadbeater, N. E.; Marco, M. Angew. Chem. 2003, 115, 11512.
[13]
Arvela, R. K.; Leadbeater, N. E.; Sangi, M. S.; Williams, V. A.; Granados, P.; Singer, R. D. J. Org. Chem. 2005, 70, 161.
[14]
Scrivanti, A.; Beghetto, V.; Bertoldini, M.; Matteoli U. Eur. J. Org. Chem. 2012, 264.
[15]
Tian, D. S.; Li, C. X.; Gu, G. X.; Peng, H.; Zhang, X.; Tang, W. J. Angew. Chem., Int. Ed. 2018, 57, 7176.
[16]
Urbani, P.; Cascio, M. G.; Ramunno, A.; Bisogno, T.; Saturninno, C.; Marzo, V. D. Bioorg. Med. Chem. 2008, 16, 7510.
[17]
Ueda, M.; Nishimura, K.; Kashima, R.; Ryu, I. Synlett 2012, 23, 1089.
[18]
(a) Huang, X. T.; Chen, Q. Y. J. Org. Chem. 2001, 66, 4651.
[18]
(b) Loy, R. N.; Sanford, M. S. Org. Lett. 2011, 13, 2548.
[19]
Ueda, M.; Nishimura, K.; Ryu, I. Synlett 2013, 24, 1683.
[20]
(a) Yoshida, M.; Gotou, T.; Ihara, M. Tetrahedron Lett. 2004, 45, 5573.
[20]
(b) Moriya, T.; Miyaura, N.; Suzuki, A. Synlett 1994, 149.
[20]
(c) Yoshida, M.; Ueda, H.; Ihara, M. Tetrahedron Lett. 2005, 46, 6705.
[20]
(d) Molander, G. A.; Sommers, E. M.; Neufeldt, S. R. J. Org. Chem. 2006, 71, 1563.
[21]
Ueda, M.; Nakakoji, D.; Kuwahara, Y.; Nishimura, K.; Ryu, I. Tetrahedron Lett. 2016, 57, 4142.
[22]
Li, C. X; Zhang, Y. Y.; Sun, Q.; Gu, T.; Peng, H.; Tang, W. J. J. Am. Chem. Soc. 2016, 138, 10774.
[23]
Liu, S. W.; Zeng, X. J.; Hammond, G. B.; Xu, B. Adv. Synth. Catal. 2018, 360, 3667.
[24]
Wu, G. J.; Xu, S.; Deng, Y. F.; Wu, C. Q.; Zhao, X.; Ji, W. Z.; Zhang, Y.; Wang, J. B. Tetrahedron 2016, 72, 8022.
[25]
(a) Urawa, Y.; Ogura, K. Tetrahedron Lett. 2003, 44, 271.
[25]
(b) Baughman, B. M.; Stennett, E.; Lipner, R. F.; Rudawsky, A. C.; Schmidtke, S. J. Phys. Chem. A 2009, 113, 8011.
[26]
(a) Furstner, A.; Voigtlander, D.; Schrader, W.; Giebel, D.; Reetz, M. T. Org. Lett. 2001, 3, 417.
[26]
(b) Song, C. E.; Shim, W. H.; Roh, E. J.; Choi, J. H. Chem. Commun. 2000, 1695.
[27]
Jadhav, S.; Rashinkar, G.; Salunkhe, R.; Kumbhar, A. Tetrahedron Lett. 2017, 58, 3201.
[28]
Hong, K.; Liu, X.; Morken, J. P. J. Am. Chem. Soc. 2014, 136, 10581.
[29]
Takeda, M.; Nagao, K.; Ohmiya, H. Angew. Chem., Int. Ed. 2020, 59, 22460.
[30]
Bonet, A.; Odachowski, M.; Leonori, D.; Essafi, S.; Aggarwal, V. K. Nat. Chem. 2014, 6, 584.
[31]
Okura, K.; Teranishi, T.; Yoshida, Y.; Shirakawa, E. Angew. Chem., Int. Ed. 2018, 57, 7186.
[32]
Fasano, V.; Winter, N.; Noble, A.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2020, 59, 8502.
[33]
He, Z. Q.; Song, F. F.; Sun, H.; Huang, Y. J. Am. Chem. Soc. 2018, 140, 2693.
[34]
Xu, J. W.; He, Z. Q.; Zhang, J. W.; Chen, J.; Huang, Y. Angew. Chem., Int. Ed. 2022, 61, e202211408.
[35]
Choghamarani, A.; Taherinia, Z. ChemistrySelect 2019, 4, 4735.
[36]
Tian, W. F.; He, K. H.; Li, N.; Fen.; Liu.; Mai, X.; Feng, L. H.; He, Y. Q. ChemistrySelect 2020, 5, 4496.
[37]
Liu, W. B; Li, J. B.; Querard, P.; Li, C. J. J. Am. Chem. Soc. 2019, 141, 6755.
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