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Recent Advances in Transition Metal-Catalyzed B—H Bond Activation for Synthesis of o-Carborane Derivatives with B—Heteroatom Bond

  • Hairui Jia ,
  • Zaozao Qiu
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  • a School of Materials and Chemistry, University of Shanghai for Science and Technology, Shanghai 200093
    b Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
    c School of Chemistry and Materials Science, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024
    d CAS Key Laboratory of Energy Regulation Materials, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
* Corresponding author. E-mail:

Received date: 2022-11-30

  Revised date: 2022-12-23

  Online published: 2023-01-05

Supported by

National Natural Science Foundation of China(92056106); Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Chinese Academy of Sciences

Abstract

Carboranes are a class of carbon-boron molecular clusters with exceptional thermal and chemical stabilities. They are finding a variety of applications in medicine, materials, and coordination/organometallic chemistry as functional building blocks. Recently, transition metal catalyzed regioselective o-carborane B—H activation has been rapidly developed, offering a series of novel methodologies for selective cage boron functionalization. The current state of functionalization of o-carboranes to form B—B, B—N, B—O, B—S, and B—halogen bonds using transition metal-catalyzed B—H activation strategy is summarized. Some reaction mechanisms are highlighted, and the future challenges and focus of the carborane B—heteroatom bond construction are discussed.

Cite this article

Hairui Jia , Zaozao Qiu . Recent Advances in Transition Metal-Catalyzed B—H Bond Activation for Synthesis of o-Carborane Derivatives with B—Heteroatom Bond[J]. Chinese Journal of Organic Chemistry, 2023 , 43(3) : 1045 -1068 . DOI: 10.6023/cjoc202211040

References

[1]
(a) Grimes, R. N. Carboranes, 3rd ed, Academic Press, Amsterdam, 2016.
[1]
(b) Hosmane, N. S.; Eagling, R. D. Handbook of Boron Science, World Scientific, 2018.
[2]
(a) Issa, F.; Kassiou, M.; Rendina, L. M. Chem. Rev. 2011, 111, 5701.
[2]
(b) Scholz, M.; Hey-Hawkins, E. Chem. Rev. 2011, 111, 7035.
[2]
(c) Valliant, J. F.; Guenther, K. J.; King, A. S.; Morel, P.; Schaffer, P.; Sogbein, O. O.; Stephenson, K. A. Coord. Chem. Rev. 2002, 232, 173.
[2]
(d) Hawthorne, M. F.; Maderna, A. Chem. Rev. 1999, 99, 3421.
[3]
(a) Jude, H.; Disteldorf, H.; Fischer, S.; Wedge, T.; Hawkridge, A. M.; Arif, A. M.; Hawthorne, M. F.; Muddiman, D. C.; Stang, P. J. J. Am. Chem. Soc. 2005, 127, 12131.
[3]
(b) Koshino, M.; Tanaka, T.; Solin, N.; Suenaga, K.; Isobe, H.; Nakamura, E. Science 2007, 316, 853.
[3]
(c) Dash, B. P.; Satapathy, R.; Gaillard, E. R.; Maguire, J. A.; Hosmane, N. S. J. Am. Chem. Soc. 2010, 132, 6578.
[3]
(d) Kung, C.-W.; Otake, K.; Buru, C. T.; Goswami, S.; Cui, Y.; Hupp, J. T.; Spokoyny, A. M.; Farha, O. K. J. Am. Chem. Soc. 2018, 140, 3871.
[3]
(e) Villago?mez, C. J.; Sasaki, T.; Tour, J. M.; Grill, L. J. Am. Chem. Soc. 2010, 132, 16848.
[3]
(f) Qian, E. Q.; Wixtrom, A. I.; Axtell, J. C.; Saebi, A.; Rehak, P.; Han, Y.; Moully, E. H.; Mosallaei, D.; Chow, S.; Messina, M.; Wang, J.-Y.; Royappa, A. T.; Rheingold, A. L.; Maynard, H. D.; Kral, P.; Spokoyny, A. M. Nat. Chem. 2017, 9, 333.
[3]
(g) Saha, A.; Oleshkevich, E.; Vin?as, C.; Teixidor, F. Adv. Mater. 2017, 29, 1704238.
[3]
(h) Guo, J.; Liu, D.; Zhang, J.; Zhang, J.; Miao, Q.; Xie, Z. Chem. Commun. 2015, 51, 12004.
[3]
(i) Jung, D.; Saleh, L. M. A.; Berkson, Z. J.; El-Kady, M. F.; Hwang, J. Y.; Mohamed, N.; Wixtrom, A. I.; Titarenko, E.; Shao, Y.; McCarthy, K.; Guo, J.; Martini, I. B.; Kraemer, S.; Wegener, E. C.; Saint-Cricq, P.; Ruehle, B.; Langeslay, R. R.; Delferro, M.; Brosmer, J. L.; Hendon, C. H.; Gallagher-Jones, M.; Rodriguez, J.; Chapman, K. W.; Miller, J. T.; Duan, X.; Kaner, R. B.; Zink, J. I.; Chmelka, B. F.; Spokoyny, A. M. Nat. Mater. 2018, 17, 341.
[3]
(j) Cui, P.-F.; Lin, Y.-J.; Li, Z.-H.; Jin, G.-X. J. Am. Chem. Soc. 2020, 142, 8532.
[3]
(k) Cui, P.-F.; Liu, X.-R.; Lin, Y.-J.; Li, Z.-H.; Jin, G.-X. J. Am. Chem. Soc. 2022, 144, 6558.
[4]
(a) Mukherjee, S.; Thilagar, P. Chem. Commun. 2016, 52, 1070.
[4]
(b) Nu?n?ez, R.; Tarre?s, M.; Ferrer-Ugalde, A.; de Biani, F. F.; Teixidor, F. Chem. Rev. 2016, 116, 14307.
[4]
(c) Li, X.; Yan, H.; Zhao, Q. Chem. Eur. J. 2016, 22, 1888.
[4]
(d) Tu, D.; Cai, S.; Fernandez, C.; Ma, H.; Wang, X.; Wang, H.; Ma, C.; Yan, H.; Lu, C.; An, Z. Angew. Chem., Int. Ed. 2019, 58, 9129.
[5]
(a) Hosmane, N. S.; Maguire, J. A. InComprehensive Organometallic Chemistry III, Vol.3, Eds.: Crabtree, R. H.; Mingos, D. M. P., Elsevier, Oxford, 2007, Chapter 5.
[5]
(b) Xie, Z. Acc. Chem. Res. 2003, 36, 1.
[5]
(c) Yao, Z.-J.; Jin, G.-X. Coord. Chem. Rev. 2013, 257, 2522.
[5]
(d) Qiu, Z.; Ren, S.; Xie, Z. Acc. Chem. Res. 2011, 44, 299.
[5]
(e) Estrada, J.; Lavallo, V. Angew. Chem., Int. Ed. 2017, 56, 9906.
[5]
(f) El-Hellani, A.; Lavallo, V. Fusing N-Heterocyclic Carbenes with Carborane Anions. Angew. Chem., Int. Ed. 2014, 53, 4489.
[5]
(g) Fisher, S. P.; Tomich, A. W.; Lovera, S. O.; Kleinsasser, J. F.; Guo, J.; Asay, M. J.; Nelson, H. M.; Lavallo, V. Chem. Rev. 2019, 119, 8262.
[5]
(h) Yao, Z.-J.; Yu, W.-B.; Lin, Y.-J.; Huang, S.-L.; Li, Z.-H.; Jin, G.-X. J. Am. Chem. Soc. 2014, 136, 2825.
[5]
(i) Gao, Y.; Guo, S.-T.; Cui, P.-F.; Aznarez, F.; Jin, G.-X. Chem. Commun. 2019, 55, 210.
[5]
(j) Cui, P.-F.; Gao, Y.; Guo, S.-T.; Lin, Y.-J.; Li, Z.-H.; Jin, G.-X. Angew. Chem., Int. Ed. 2019, 58, 8129.
[6]
Kasar, R. A.; Knudsen, G. M.; Kahl, S. B. Inorg. Chem. 1999, 38, 2936.
[7]
(a) Potenza, J. A.; Lipscomb, W. N.; Vickers, G. D.; Schroeder, H. J. Am. Chem. Soc. 1966, 88, 628.
[7]
(b) Zheng, Z.; Knobler, C. B.; Mortimer, M. D.; Kong, G.; Hawthorne, M. F. Inorg. Chem. 1996, 35, 1235.
[7]
(c) Herzog, A.; Maderna, A.; Harakas, G. N.; Knobler, C. B.; Hawthorne, M. F. Chem. Eur. J. 1999, 5, 1212.
[7]
(d) Teixidor, F.; Barberà, G.; Vi?s, C.; Sillanp??, R.; Kivek?s, R. Inorg. Chem. 2006, 45, 3496.
[8]
Ahrens, V. M.; Frank, R.; Boehnke, S.; Schütz, C. L.; Hampel, G.; Iffland, D. S.; Bings, N. H.; Hey-Hawkins, E; Beck-Sickinger, A. G. ChemMedChem 2015, 10, 164.
[9]
Hawthorne, M. F.; Wegner, P. A. J. Am. Chem. Soc. 1968, 90, 896.
[10]
Ramachandran, B. M.; Knobler, C. B.; Hawthorne, M. F. Inorg. Chem. 2006, 45, 336.
[11]
Safronov, A. V.; Sevryugina, Y. V.; Jalisatgi, S. S.; Kennedy, R. D.; Barnes, C. L.; Hawthorne, M. F. Inorg. Chem. 2012, 51, 2629.
[12]
(a) Olid, D.; Nú?ez, R.; Vi?as, C.; Teixidor, F. Chem. Soc. Rev. 2013, 42, 3318.
[12]
(b) Sivaev, I. B.; Anufriev, S. A.; Shmal'ko, A. V. InAdvances in Catalysis, Vol.71, Eds.: Diéguez, M.; Nú?ez, R., Academic Press, 2022, p. 47.
[13]
(a) Qiu, Z.; Xie, Z. Acc. Chem. Res. 2021, 54, 4065.
[13]
(b) Au, Y. K.; Xie, Z. Bull. Chem. Soc. Jpn. 2021, 94, 879.
[13]
(c) Quan, Y.; Qiu, Z.; Xie, Z. Chem. Eur. J. 2018, 24, 2795.
[13]
(d) Zhang, H.; Qiu, Z.; Xie, Z. Chin. J. Org. Chem. 2020, 40, 3203. (in Chinese)
[13]
(张慧芳, 邱早早, 谢作伟, 有机化学, 2020, 40, 3203.)
[13]
(e) Cui, P.-F.; Liu, X.-R.; Guo, S.-T.; Lin, Y.-J.; Jin, G.-X. J. Am. Chem. Soc. 2021, 143, 5099.
[13]
(f) Liu, X.-R.; Cui, P.-F.; Guo, S.-T.; Yuan, R.-Z.; Jin, G.-X. Inorg. Chem. Front. 2021, 8, 4349.
[13]
(g) Guo, S.-T.; Cui, P.-F.; Liu, X.-R.; Jin, G.-X. J. Am. Chem. Soc. 2022, 144, 22221.
[14]
Cheng, R.; Qiu, Z.; Xie, Z. Nat. Commun. 2017, 8, 14827.
[15]
(a) Wu, J.; Cao, K.; Zhang, C.-Y.; Xu, T.-T.; Ding, L.-F.; Li, B.; Yang, J. Org. Lett. 2019, 21, 5986.
[15]
(b) Wu, J.; Cao, K.; Zhang, C.-Y.; Xu, T.-T.; Wen, X.-Y.; Li, B.; Yang, J. Inorg. Chem. 2020, 59, 17340.
[16]
Luo, D.; Fu, Y.; Lu, J.-Y. Inorg. Chem. 2022, 61, 13756.
[17]
Quan, Y.; Xie, Z. J. Am. Chem. Soc. 2014, 136, 15513.
[18]
Lyu, H.; Quan, Y.; Xie, Z. J. Am. Chem. Soc. 2016, 138, 12727.
[19]
Li, H.; Bai, F.; Yan, H.; Lu, C.; Bregadze, V. I. Eur. J. Org. Chem. 2017, 1343.
[20]
Baek, Y.; Kim, S.; Son, J.-Y.; Lee, K.; Kim, D.; Lee, P. H. ACS Catal. 2019, 9, 10418.
[21]
Han, G. U.; Baek, Y.; Lee, K.; Shin, S.; Chan Noh, H.; Lee, P. H. Org. Lett. 2021, 23, 416.
[22]
Han, G. U.; Shin, S.; Baek, Y.; Kim, D.; Lee, K.; Kim, J. G.; Lee, P. H. Org. Lett. 2021, 23, 8622.
[23]
Zhang, L. B.; Xie, Z. Org. Lett. 2022, 24, 7077.
[24]
Lyu, H.; Xie, Z. Chem. Commun. 2022, 58, 8392.
[25]
Au, Y. K.; Lyu, H.; Quan, Y.; Xie, Z. J. Am. Chem. Soc. 2019, 141, 12855.
[26]
Guo, C.; Qiu, Z.; Xie, Z. ACS Catal. 2021, 11, 2134.
[27]
Ge, Y.; Zhang, J.; Qiu, Z.; Xie, Z. Angew. Chem., Int. Ed. 2020, 59, 4851.
[28]
Ge, Y.; Qiu, Z.; Xie, Z. Acta Chim. Sinica 2022, 80, 432. (in Chinese)
[28]
(葛懿修, 邱早早, 谢作伟, 化学学报, 2022, 80, 432.)
[29]
Au, Y. K.; Zhang, J.; Quan, Y.; Xie, Z. J. Am. Chem. Soc. 2021, 143, 4148.
[30]
Cao, K.; Huang, Y.; Yang, J.; Wu, J. Chem. Commun. 2015, 51, 7257.
[31]
Ma, Y. N.; Gao, Y.; Ma, Y.; Wang, Y.; Ren, H.; Chen, X. J. Am. Chem. Soc. 2022, 144, 8371.
[32]
Guo, S. T.; Cui, P. F.; Yuan, R. Z.; Jin, G.-X. Chem. Commun. 2021, 57, 2412.
[33]
Lyu, H.; Quan, Y.; Xie, Z. Angew. Chem., Int. Ed. 2016, 55, 11840.
[34]
Ham, H.; Shin, S.; Ko, G. H.; Han, S. H.; Han, G. U.; Maeng, C.; Kim, T. H.; Noh, H. C.; Lee, K.; Kim, H.; Yang, H.; Lee, P. H. J. Org. Chem. 2021, 86, 15153.
[35]
Au, Y. K.; Lyu, H.; Quan, Y.; Xie, Z. Chin. J. Chem. 2020, 38, 383.
[36]
Chen, Y.; Au, Y. K.; Quan, Y.; Xie, Z. Sci. China. Chem. 2019, 62, 74.
[37]
Au, Y. K.; Lyu, H.; Quan, Y.; Xie, Z. J. Am. Chem. Soc. 2020, 142, 6940.
[38]
Chen, Y.; Quan, Y.; Xie, Z. Chem. Commun. 2020, 56, 12997.
[39]
Cheng, B.; Chen, Y.; Zhou, P.; Xie, Z. Chem. Commun. 2022, 58, 629.
[40]
Li, C. X.; Zhang, H. Y.; Wong, T. Y.; Cao, H. J.; Yan, H.; Lu, C. S. Org. Lett. 2017, 19, 5178.
[41]
Fu, Y.; Li, Y.; Luo, D.; Lu, Y.; Huang, J.; Yang, Z.; Lu, J.; Jiang, Y. Y.; Lu, J. Y. Inorg. Chem. 2022, 61, 911.
[42]
Cui, C. X.; Zhang, J.; Qiu, Z.; Xie, Z. Dalton. Trans. 2020, 49, 1380.
[43]
Cao, K.; Xu, T. T.; Wu, J.; Jiang, L.; Yang, J. Chem. Commun. 2016, 52, 11446.
[44]
Lyu, H.; Quan, Y.; Xie, Z. Chem. Eur. J. 2017, 23, 14866.
[45]
Lyu, H.; Zhang, J.; Yang, J.; Quan, Y.; Xie, Z. J. Am. Chem. Soc. 2019, 141, 4219.
[46]
Zhang, Z. Y.; Zhang, X.; Yuan, J.; Yue, C. D.; Meng, S.; Chen, J.; Yu, G. A.; Che, C. M. Chem. Eur. J. 2020, 26, 5037.
[47]
Qiu, Z.; Quan, Y.; Xie, Z. J. Am. Chem. Soc. 2013, 135, 12192.
[48]
Xu, T.-T.; Zhang, C.-Y.; Cao, K.; Wu, J.; Jiang, L.; Li, J.; Li, B.; Yang, J. ChemistrySelect 2017, 2, 3396.
[49]
Zhang, J.; Xie, Z. Angew. Chem., Int. Ed. 2022, 61, e202202675.
[50]
(a) Cheng, R.; Li, B.; Wu, J.; Zhang, J.; Qiu, Z.; Tang, W.; You, S. L.; Tang, Y.; Xie, Z. J. Am. Chem. Soc. 2018, 140, 4508.
[50]
(b) Cheng, R.; Zhang, J.; Zhang, H.; Qiu, Z.; Xie, Z. Nat. Commun. 2021, 12, 7146.
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