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2023 , Vol. 43 >Issue 5: 1751 - 1760

DOI: https://doi.org/10.6023/cjoc202212022

综述与进展

锆、钛介导的烯烃、炔烃硼氢化

  • 李思达 ,
  • 舒兴中 ,
  • 吴立朋
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  • a 中国科学院兰州化学物理研究所 羰基合成与选择氧化国家重点实验室 兰州 73000
    b 兰州大学化学化工学院 功能有机分子化学国家重点实验室 兰州 73000
    c 中国科学院大学 北京 100049

收稿日期: 2022-12-16

  修回日期: 2023-01-09

  网络出版日期: 2023-01-18

基金资助

国家自然科学基金(22271295); 中国科学院兰州化学物理研究所青年科技工作者协同创新联盟合作基金(HZJJ21-01)

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Zirconium and Titanium Mediated Hydroboration of Alkenes and Alkynes

  • Sida Li ,
  • Xing-Zhong Shu ,
  • Lipeng Wu
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  • a State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000
    b State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000
    c University of Chinese Academy of Sciences, Beijing 100049
* Corresponding authors. E-mail: ;

Received date: 2022-12-16

  Revised date: 2023-01-09

  Online published: 2023-01-18

Supported by

National Natural Science Foundation of China(22271295); Cooperation Foundation of Lanzhou Institute of Chemical Physics for Young Scholars(HZJJ21-01)

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摘要

过渡金属催化的烯烃、炔烃硼氢化反应是制备硼酸酯类化合物最为有效的方法之一, 该反应具有100%的原子经济性, 原料简单易得, 产物多样性可调等优点. 已知的金属催化剂大都依赖于铑、铱、钯、铂、钴、铁、铜等后过渡金属, 而使用前过渡金属锆、钛作为催化剂的反应体系则鲜有报道. 总结了锆、钛介导的(化学计量与催化量)烯烃、炔烃硼氢化反应的研究现状, 并对今后锆、钛催化的烯烃、炔烃硼氢化反应的发展进行了展望.

关键词： 锆; 钛; 烯烃; 炔烃; 硼氢化

本文引用格式

李思达 , 舒兴中 , 吴立朋 . 锆、钛介导的烯烃、炔烃硼氢化[J]. 有机化学, 2023 , 43(5) : 1751 -1760 . DOI: 10.6023/cjoc202212022

Abstract

The transition metal-catalyzed hydroboration of alkenes and alkynes is one of the most efficient way for the production of boronate esters. This type of reaction is 100% atom economic, the starting material is readily available, and the products are diverse. It is noticed that most of the known catalytic systems are based on late-transition-metals such as Rh, Ir, Pd, Pt, Co, Fe and Cu. The use of early-transition-metals of zirconium and titanium, on the other hand, is very scarce. In this short review, the development of application in zirconium and titanium mediated hydroboration of alkene and alkyne is summarized, and the research trends of this area are also discussed.

Key words： zirconium; titanium; alkenes; alkynes; hydroboration

参考文献

[1]
(a) Hartwig, J. F. Acc. Chem. Res. 2012, 45, 864.
[1]
(b) Liu, Q.; Tian, B.; Tian, P.; Tong, X. F.; Lin, G.-Q. Chin. J. Org. Chem. 2015, 35, 1. (in Chinese)
[1]
(刘强, 田兵, 田平, 童晓峰, 林国强, 有机化学, 2015, 35, 1.)
[1]
(c) Cheng, Q. Q.; Xu, H.; Zhu, S. F.; Zhou, Q. L. Acta Chim. Sinica 2015, 73, 326. (in Chinese)
[1]
(程清卿, 许唤, 朱守非, 周其林, 化学学报, 2015, 73, 326.)
[1]
(d) Liu, Y.; Zhang, W. Chin. J. Org. Chem. 2016, 36, 2249. (in Chinese)
[1]
(刘媛媛, 张万斌, 有机化学, 2016, 36, 2249.)
[2]
(a) Negishi, E.-I.; Racherla, U. S. Heteroat. Chem. 1992, 3, 201.
[2]
(b) Chen, J.; Guo, J.; Lu, Z. Chin. J. Chem. 2018, 36, 1075.
[2]
(c) Obligacion, J. V.; Chirik, P. J. Nat. Rev. Chem. 2018, 2, 15.
[2]
(d) Guo, J.; Cheng, Z.; Chen, J.; Chen, X.; Lu, Z. Acc. Chem. Res. 2021, 54, 2701.
[2]
(e) Lu, H. X; Li, B. J. Chin. J. Org. Chem. 2022, 42, 3167. (in Chinese)
[2]
(陆候祥, 李必杰, 有机化学, 2022, 42, 3167.)
[3]
M?nnig, D.; N?th, H. Angew. Chem., Int. Ed. 1985, 24, 878.
[4]
(a) Crudden, C. M.; Hleba, Y. B.; Chen, A. C. J. Am. Chem. Soc. 2004, 126, 9200.
[4]
(b) Huang, J.-Z.; Yan, W.-X.; Tan, C.-W.; Wu, W.-Q.; Jiang, H.-F. Chem. Commun. 2018, 54, 1770.
[4]
(c) Gunanathan, C.; H?lscher, M.; Pan, F.; Leitner, W. J. Am. Chem. Soc. 2012, 134, 14349.
[4]
(d) Xu, S.-M.; Zhang, Y.-Z.; Li, B.; Liu, S.-Y. J. Am. Chem. Soc. 2016, 138, 14566.
[4]
(e) Sun, Y.; Guan, R.; Liu, Z.-H.; Wang, Y.-M. Chin. J. Org. Chem. 2020, 40, 899. (in Chinese)
[4]
(孙越, 关瑞, 刘兆洪, 王也铭, 有机化学, 2020, 40, 899.)
[4]
(f) Huang, M.-Y.; Zhu, S.-F. Chem. J. Chin. Univ. 2020, 41, 1426. (in Chinese)
[4]
(黄明耀, 朱守非, 高等学校化学学报, 2020, 41, 1426.)
[5]
(a) Marek, I. Titanium and Zirconium in Organic Synthesis, Wiley-VCH, Weinheim, 2002.
[5]
(b) Yan, X.; Xi, C. Coord. Chem. Rev. 2016, 308, 22.
[5]
(c) Man?en, M.; Schafer, L. L. Chem. Soc. Rev. 2020, 49, 6947.
[5]
(d) Rosenthal, U. Chem. Soc. Rev. 2020, 49, 2119.
[5]
(e) Wu, X.; Chang, Y.; Lin, S. Chem 2022, 8, 1805.
[6]
Cole, T. E.; Quintanilla, R.; Rodewald, S. Organometallics 1991, 10, 3777.
[7]
Cole, T. E.; Quintanilla, R. Tetrahedron 1995, 51, 4297.
[8]
Pereira, S.; Srebnik, M. Organometallics 1995, 14, 3127.
[9]
Wang, Y. D.; Kimball, G.; Prashada, A. S.; Wang, Y. Tetrahedron Lett. 2005, 46, 8777.
[10]
Sakae, R.; Hirano, K.; Satoh, T.; Miura, M. Chem. Lett. 2013, 42, 1128.
[11]
Spencer, J. A.; Jamieson, C.; Talbot, E. P. A. Org. Lett. 2017, 19, 3891.
[12]
Birepinte, M.; Liautard, V.; Chabaud, L.; Pucheault, M. Org. Lett. 2020, 22, 2838.
[13]
Pereira, S.; Srebnik, M. J. Am. Chem. Soc. 1996, 118, 909.
[14]
Shi, X. N.; Li, S. D.; Wu, L. P. Angew. Chem., Int. Ed. 2019, 58, 16167.
[15]
Wang, X. J.; Cui, X.; Li, S. D.; Wang, Y.; Jiao, H.-J.; Xia, C. G.; Wu, L. P. Angew. Chem., Int. Ed. 2020, 59, 13608.
[16]
(a) Isagawa, K.; Sano, H.; Hattori, M.; Otsuji, Y. Chem. Lett. 1979, 8, 1069.
[16]
(b) Lee, H. S.; Isagawa, K.; Toyoda, H.; Otsuji, Y. Chem. Lett. 1984, 13, 673.
[16]
(c) Lee, H. S.; Isagawa, K.; Otsuji, Y. Chem. Lett. 1984, 13, 363.
[17]
Burgess, K.; Donk, W. A. V. D. Organometallics 1994, 13, 3616.
[18]
Hartwig, J. F.; He, X. M. J. Am. Chem. Soc. 1996, 118, 1696.
[19]
Hartwig, J. F.; Muhoro, C. N. Organometallics 2000, 19, 30.
[20]
(a) Pender, M. J.; Wideman, T.; Carroll, P. J.; Sneddon, L. G. J. Am. Chem. Soc. 1998, 120, 9108.
[20]
(b) Pender, M. J.; Carroll, P. J.; Sneddon, L. G. J. Am. Chem. Soc. 2001, 123, 12222.
[21]
Khusainova, L. I.; Khafizova, L. O.; Tyumkina, T. V.; Ryazanov, K. S.; Dzhemilev, U. M. J. Organomet. Chem. 2017, 832, 12.
[22]
Motry, D. H.; Smith, M. R. J. Am. Chem. Soc. 1995, 117, 6615.
[23]
Motry, D. H.; Brazil, A. G.; Smith, M. R. J. Am. Chem. Soc. 1997, 119, 2743.
[24]
Khusainova, L. I.; Khafizova, L. O.; Ryazanov, K. S.; Tyumkina, T. V.; Dzhemilev, U. M. J. Organomet. Chem. 2019, 898, 120858.
[25]
Bhattacharjee, J.; Harinath, A.; Bano, K.; Panda, T. K. ACS Omega 2020, 5, 1595.
[26]
(a) Zhang, T. X.; Zhang, Y.; Zhang, W. X.; Luo, M. M. Adv. Synth. Catal. 2013, 355, 2775.
[26]
(b) Fortier, S.; Gomez-Torres, A. Chem. Commun. 2021, 57, 10292.
[26]
(c) Wu, Y.; Zhao, T.; Rong, J.; Rao, Y.; Zhou, M.; Yin, B.; Ni, X.; Osuka, A.; Xu, L.; Song, J. Angew. Chem., Int. Ed. 2022, 61, e202201327.
[26]
(d) Hilche, T.; Younas, S. L.; Gans?uer, A.; Streuff, J. ChemCatChem 2022, 14, e202200530.
[27]
(a) Iwamoto, H.; Kubota, K.; Ito, H. Chem. Commun. 2016, 52, 5916.
[27]
(b) Peng, J.; Docherty, J. H.; Dominey, A. P.; Thomas, S. P. Chem. Commun. 2017, 53, 4726.
[27]
(c) Chen, J.; Shen, X.; Lu, Z. Angew. Chem., Int. Ed. 2021, 60, 690.
[28]
(a) Chen, J.; Lu, Z. Org. Chem. Front. 2018, 5, 260.
[28]
(b) Mas-Rosello, J.; Herraiz, A. G.; Audic, B.; Laverny, A.; Cramer, N. Angew. Chem., Int. Ed. 2021, 60, 13198.
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