过渡金属催化硼-氢键活化合成含硼-杂原子键邻碳硼烷衍生物的研究进展

doi:10.6023/cjoc202211040

有机化学 ›› 2023, Vol. 43 ›› Issue (3): 1045-1068.DOI: 10.6023/cjoc202211040 上一篇下一篇

所属专题：中国女科学家专辑

综述与进展

过渡金属催化硼-氢键活化合成含硼-杂原子键邻碳硼烷衍生物的研究进展

贾海瑞^a^,^b, 邱早早^b^,^c^,^d^,^*()

a 上海理工大学材料与化学学院上海 200093
b 中国科学院上海有机化学研究所沪港化学合成联合实验室上海 200032
c 中国科学院大学杭州高等研究院化学与材料科学学院杭州 310024
d 中国科学院上海有机化学研究所能量调控材料重点实验室上海 200032

收稿日期:2022-11-30 修回日期:2022-12-23 发布日期:2023-01-05
通讯作者: 邱早早
基金资助:
国家自然科学基金(92056106); 中国科学院沪港化学合成联合实验室资助项目

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

Hairui Jia^a^,^b, Zaozao Qiu^b^,^c^,^d()

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

Received:2022-11-30 Revised:2022-12-23 Published:2023-01-05
Contact: Zaozao Qiu
Supported by:
National Natural Science Foundation of China(92056106); Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Chinese Academy of Sciences

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摘要/Abstract

十二顶点碳硼烷是一类含有碳、氢及硼原子的簇合物, 具有特殊的热稳定性和化学稳定性, 在医药、材料、能源、配位化学及金属有机化学中都得到广泛的应用. 近年来, 过渡金属催化的碳硼烷直接硼-氢键活化发展迅速, 为硼顶点选择性官能团化提供了一系列新的高效路径. 总结了利用过渡金属催化硼-氢键活化策略来实现邻碳硼烷硼-硼、硼-氮、硼-氧、硼-硫及硼-卤键构建的研究进展, 同时对部分反应机理进行了讨论, 并就该研究领域所面临的挑战和发展前景进行了展望.

关键词: 碳硼烷, 硼-氢键活化, 过渡金属催化, 硼-杂原子键

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.

Key words: carborane, B—H activation, transition metal catalysis, B—heteroatom bond

引用此文

贾海瑞, 邱早早. 过渡金属催化硼-氢键活化合成含硼-杂原子键邻碳硼烷衍生物的研究进展[J]. 有机化学, 2023, 43(3): 1045-1068.

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.

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图/表 35

图式1. 邻碳硼烷的硼-杂原子键构筑路径

Scheme 1. Synthetic approaches to construct B—heteroatom bond of o-carboranes

图式2. 铱催化B(3,6)-双硼基化或B(3)-硼基化

Scheme 2. Ir-catalyzed B(3,6)-diborylation or B(3)-borylation

图式3. 铱催化B(4)-硼基化

Scheme 3. Ir-catalyzed B(4)-borylation

图式4. 钯催化合成联-碳硼烷

Scheme 4. Pd-catalyzed synthesis of bis-o-carboranes

图式5. 钌催化磺酰叠氮参与的B(4)-胺基化

Scheme 5. Ru-catalyzed B(4)-amination with sulfonyl azides

图式6. 铱催化叠氮参与的B(4)-胺基化

Scheme 6. Ir-catalyzed B(4)-amination with azides

图式7. 钯催化O-苯甲酰羟胺参与的B(4)-胺基化

Scheme 7. Pd-catalyzed B(4)-amination with O-benzoyl hydroxylamines

图式8. 铑催化二噁唑酮参与的B(4)-胺基化

Scheme 8. Rh-catalyzed B(4)-amination with dioxazolones

图式9. 铱催化二噁唑酮参与的B(4)-胺基化

Scheme 9. Ir-catalyzed B(4)-amination with dioxazolones

图式10. 铱催化2,1-苯并异噁唑参与的B(4)-胺基化

Scheme 10. Ir-catalyzed B(4)-amination with 2,1-benzisoxazoles

图式11. 铱催化伯胺参与的B(4)-胺基化

Scheme 11. Ir-catalyzed B(4)-amination with primaryamine

图式12. 铱催化芳酰胺参与的串联B(4)-芳基化和B(5)-胺基化

Scheme 12. Ir-catalyzed cascade B(4)-arylation and B(5)-amination with benzamides

图式13. 钯迁移实现的一锅法B(3)-烯基化B(4)-酰胺基化

Scheme 13. One-pot B(3)-alkenylation and B(4)-amidination via Pd-migration

图式14. 钯迁移实现的一锅法B(3)-烯基化B(4)-胺基化

Scheme 14. One-pot B(3)-alkenylation and B(4)-amination via Pd-migration

图式15. 铱催化氨气参与的B(3)-氨基化

Scheme 15. Ir-catalyzed B(3)-amination with ammonia gas

图式16. 铑催化磺酰胺参与的B(3)-胺基化

Scheme 16. Rh-catalyzed B(3)-amination with sulfonyl amides

图式17. 钯催化O-苯甲酰羟胺参与的B(9)-胺基化

Scheme 17. Pd-catalyzed B(9)-amination with O-benzoyl hydroxylamines

图式18. 钯催化酸性氮源参与的B(9)-胺基化

Scheme 18. Pd-catalyzed B(9)-amination with acidic nitrogen sources

图式19. 铑催化氧气参与的B(4)-羟基化

Scheme 19. Rh-catalyzed B(4)-hydroxylation with O2

图式20. 钯催化二羧酸碘苯参与的B(4)-酰氧基化

Scheme 20. Pd-catalyzed B(4)-acyloxylation with phenyliodonium dicarboxylates

图式21. 铱催化芳基羧酸参与的串联B(4)-芳基化和B(5)-酰氧基化

Scheme 21. Ir-catalyzed cascade B(4)-arylation and B(5)-amination with benzoic acids

图式22. 铜催化电化学条件下的B(4)-氧化和B(4,5)-双氧化

Scheme 22. Cu-catalyzed electrochemical selective B(4)-oxygenation or B(4,5)-dioxygenation

图式23. 铜催化二硫化物参与的B(4,5)-双硫化

Scheme 23. Cu-catalyzed B(4,5)-disulfenylation with disulfides

图式24. 钯迁移实现的一锅法构建硼-碳和硼-氧/硫键

Scheme 24. One-pot construction of B—C and B—O/S bonds via Pd-migration

图式25. 铑催化二芳基乙炔和铜盐参与的B(3,4,5)-串联三官能团化

Scheme 25. Rh-catalyzed cascade B(3,4,5)-trifunctionalization with diarylalkynes and copper salts

图式26. 铑催化羧酸参与的B(3)-酰氧基化

Scheme 26. Rh-catalyzed B(3)-acyloxylation with carboxylic acids

图式27. 钯催化羧酸参与的B(3)-和B(3,4)-酰氧基化

Scheme 27. Pd-catalyzed B(3)- and B(3,4)-acyloxylation with carboxylic acids

图式28. 钯催化分子内B(3/4)—H和O—H的脱氢偶联

Scheme 28. Pd-catalyzed intramolecular dehydrogenative coupling of B(3/4)—H and O—H

图式29. 钯催化醋酸碘苯参与的B(8,9,10,12)-四酰氧基化和B(8/9)-酰氧基化

Scheme 29. Pd-catalyzed B(8,9,10,12)-tetraacyloxylation and B(8/9)-acyloxylation with PhI(OAc)2

图式30. 铱催化B(4)-卤化

Scheme 30. Ir-catalyzed B(4)-halogenation

图式31. 钯催化乙酸碘参与的B(4,5)-碘化

Scheme 31. Pd-catalyzed B(4,5)-iodination with IOAc

图式32. 钯催化1-氟吡啶四氟硼酸盐参与的B(4,7,8)-三氟化

Scheme 32. Pd-catalyzed B(4,7,8)-triflorination with 1-fluoro- pyridinium tetrafluoroborate

图式33. 钯催化芳基卤化物参与的B(3)-卤化

Scheme 33. Pd-catalyzed B(3)-halogination with aryl halides

图式34. 钯催化1-氟吡啶三氟甲磺酸盐参与的B(8,9,10,12)-四氟化

Scheme 34. Pd-catalyzed B(8,9,10,12)-tetraflorination with 1- fluoropyridinium trifluoromethanesulfate

图式35. 钯催化FeCl3参与的B(8/9)-氯化

Scheme 35. Pd-catalyzed B(8/9)-chlorination with FeCl3

参考文献 50

[1]	(a) Grimes, R. N. Carboranes, 3rd ed, Academic Press, Amsterdam, 2016.
	(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. doi: 10.1021/cr2000866
	(b) Scholz, M.; Hey-Hawkins, E. Chem. Rev. 2011, 111, 7035. doi: 10.1021/cr200038x
	(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. doi: 10.1016/S0010-8545(02)00087-5
	(d) Hawthorne, M. F.; Maderna, A. Chem. Rev. 1999, 99, 3421. doi: 10.1021/cr980442h
[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. doi: 10.1021/ja053050i
	(b) Koshino, M.; Tanaka, T.; Solin, N.; Suenaga, K.; Isobe, H.; Nakamura, E. Science 2007, 316, 853. doi: 10.1126/science.1138690
	(c) Dash, B. P.; Satapathy, R.; Gaillard, E. R.; Maguire, J. A.; Hosmane, N. S. J. Am. Chem. Soc. 2010, 132, 6578. doi: 10.1021/ja101845m
	(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. doi: 10.1021/jacs.8b00605
	(e) Villagómez, C. J.; Sasaki, T.; Tour, J. M.; Grill, L. J. Am. Chem. Soc. 2010, 132, 16848. doi: 10.1021/ja105542j
	(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. doi: 10.1038/nchem.2686
	(g) Saha, A.; Oleshkevich, E.; Viñas, C.; Teixidor, F. Adv. Mater. 2017, 29, 1704238. doi: 10.1002/adma.v29.46
	(h) Guo, J.; Liu, D.; Zhang, J.; Zhang, J.; Miao, Q.; Xie, Z. Chem. Commun. 2015, 51, 12004. doi: 10.1039/C5CC03608A
	(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. doi: 10.1038/s41563-018-0021-9
	(j) Cui, P.-F.; Lin, Y.-J.; Li, Z.-H.; Jin, G.-X. J. Am. Chem. Soc. 2020, 142, 8532. doi: 10.1021/jacs.0c03176
	(k) Cui, P.-F.; Liu, X.-R.; Lin, Y.-J.; Li, Z.-H.; Jin, G.-X. J. Am. Chem. Soc. 2022, 144, 6558. doi: 10.1021/jacs.2c01668
[4]	(a) Mukherjee, S.; Thilagar, P. Chem. Commun. 2016, 52, 1070. doi: 10.1039/C5CC08213G
	(b) Núñez, R.; Tarrés, M.; Ferrer-Ugalde, A.; de Biani, F. F.; Teixidor, F. Chem. Rev. 2016, 116, 14307. doi: 10.1021/acs.chemrev.6b00198
	(c) Li, X.; Yan, H.; Zhao, Q. Chem. Eur. J. 2016, 22, 1888. doi: 10.1002/chem.201503456
	(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. doi: 10.1002/anie.v58.27
[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. pmid: 30707011
	(b) Xie, Z. Acc. Chem. Res. 2003, 36, 1. doi: 10.1021/ar010146i pmid: 30707011
	(c) Yao, Z.-J.; Jin, G.-X. Coord. Chem. Rev. 2013, 257, 2522. doi: 10.1016/j.ccr.2013.02.004 pmid: 30707011
	(d) Qiu, Z.; Ren, S.; Xie, Z. Acc. Chem. Res. 2011, 44, 299. doi: 10.1021/ar100156f pmid: 30707011
	(e) Estrada, J.; Lavallo, V. Angew. Chem., Int. Ed. 2017, 56, 9906. doi: 10.1002/anie.201705857 pmid: 30707011
	(f) El-Hellani, A.; Lavallo, V. Fusing N-Heterocyclic Carbenes with Carborane Anions. Angew. Chem., Int. Ed. 2014, 53, 4489. doi: 10.1002/anie.201402445 pmid: 30707011
	(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. doi: 10.1021/acs.chemrev.8b00551 pmid: 30707011
	(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. doi: 10.1021/ja4115665 pmid: 30707011
	(i) Gao, Y.; Guo, S.-T.; Cui, P.-F.; Aznarez, F.; Jin, G.-X. Chem. Commun. 2019, 55, 210. doi: 10.1039/C8CC09084J pmid: 30707011
	(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. doi: 10.1002/anie.v58.24 pmid: 30707011
[6]	Kasar, R. A.; Knudsen, G. M.; Kahl, S. B. Inorg. Chem. 1999, 38, 2936. doi: 10.1021/ic990037o
[7]	(a) Potenza, J. A.; Lipscomb, W. N.; Vickers, G. D.; Schroeder, H. J. Am. Chem. Soc. 1966, 88, 628. doi: 10.1021/ja00955a059
	(b) Zheng, Z.; Knobler, C. B.; Mortimer, M. D.; Kong, G.; Hawthorne, M. F. Inorg. Chem. 1996, 35, 1235. doi: 10.1021/ic951069o
	(c) Herzog, A.; Maderna, A.; Harakas, G. N.; Knobler, C. B.; Hawthorne, M. F. Chem. Eur. J. 1999, 5, 1212. doi: 10.1002/(ISSN)1521-3765
	(d) Teixidor, F.; Barberà, G.; Viñs, C.; Sillanpää, R.; Kivekäs, R. Inorg. Chem. 2006, 45, 3496. doi: 10.1021/ic060124y
[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. doi: 10.1002/cmdc.v10.1
[9]	Hawthorne, M. F.; Wegner, P. A. J. Am. Chem. Soc. 1968, 90, 896. doi: 10.1021/ja01006a009
[10]	Ramachandran, B. M.; Knobler, C. B.; Hawthorne, M. F. Inorg. Chem. 2006, 45, 336. pmid: 16390073
[11]	Safronov, A. V.; Sevryugina, Y. V.; Jalisatgi, S. S.; Kennedy, R. D.; Barnes, C. L.; Hawthorne, M. F. Inorg. Chem. 2012, 51, 2629. doi: 10.1021/ic2025846
[12]	(a) Olid, D.; Núñez, R.; Viñas, C.; Teixidor, F. Chem. Soc. Rev. 2013, 42, 3318. doi: 10.1039/c2cs35441a
	(b) Sivaev, I. B.; Anufriev, S. A.; Shmal'ko, A. V. InAdvances in Catalysis, Vol.71, Eds.: Diéguez, M.; Núñez, R., Academic Press, 2022, p. 47.
[13]	(a) Qiu, Z.; Xie, Z. Acc. Chem. Res. 2021, 54, 4065. doi: 10.1021/acs.accounts.1c00460
	(b) Au, Y. K.; Xie, Z. Bull. Chem. Soc. Jpn. 2021, 94, 879. doi: 10.1246/bcsj.20200366
	(c) Quan, Y.; Qiu, Z.; Xie, Z. Chem. Eur. J. 2018, 24, 2795. doi: 10.1002/chem.v24.12
	(d) Zhang, H.; Qiu, Z.; Xie, Z. Chin. J. Org. Chem. 2020, 40, 3203. (in Chinese) doi: 10.6023/cjoc202005079
	(张慧芳, 邱早早, 谢作伟, 有机化学, 2020, 40, 3203.) doi: 10.6023/cjoc202005079
	(e) Cui, P.-F.; Liu, X.-R.; Guo, S.-T.; Lin, Y.-J.; Jin, G.-X. J. Am. Chem. Soc. 2021, 143, 5099. doi: 10.1021/jacs.1c00779
	(f) Liu, X.-R.; Cui, P.-F.; Guo, S.-T.; Yuan, R.-Z.; Jin, G.-X. Inorg. Chem. Front. 2021, 8, 4349. doi: 10.1039/D1QI00732G
	(g) Guo, S.-T.; Cui, P.-F.; Liu, X.-R.; Jin, G.-X. J. Am. Chem. Soc. 2022, 144, 22221. doi: 10.1021/jacs.2c10201
[14]	Cheng, R.; Qiu, Z.; Xie, Z. Nat. Commun. 2017, 8, 14827. doi: 10.1038/ncomms14827
[15]	(a) Wu, J.; Cao, K.; Zhang, C.-Y.; Xu, T.-T.; Ding, L.-F.; Li, B.; Yang, J. Org. Lett. 2019, 21, 5986. doi: 10.1021/acs.orglett.9b02129
	(b) Wu, J.; Cao, K.; Zhang, C.-Y.; Xu, T.-T.; Wen, X.-Y.; Li, B.; Yang, J. Inorg. Chem. 2020, 59, 17340. doi: 10.1021/acs.inorgchem.0c02638
[16]	Luo, D.; Fu, Y.; Lu, J.-Y. Inorg. Chem. 2022, 61, 13756. doi: 10.1021/acs.inorgchem.2c01360
[17]	Quan, Y.; Xie, Z. J. Am. Chem. Soc. 2014, 136, 15513. doi: 10.1021/ja509557j
[18]	Lyu, H.; Quan, Y.; Xie, Z. J. Am. Chem. Soc. 2016, 138, 12727. doi: 10.1021/jacs.6b07086
[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. doi: 10.1021/acscatal.9b03380
[21]	Han, G. U.; Baek, Y.; Lee, K.; Shin, S.; Chan Noh, H.; Lee, P. H. Org. Lett. 2021, 23, 416. doi: 10.1021/acs.orglett.0c03927 pmid: 33377789
[22]	Han, G. U.; Shin, S.; Baek, Y.; Kim, D.; Lee, K.; Kim, J. G.; Lee, P. H. Org. Lett. 2021, 23, 8622. doi: 10.1021/acs.orglett.1c03336
[23]	Zhang, L. B.; Xie, Z. Org. Lett. 2022, 24, 7077. doi: 10.1021/acs.orglett.2c02590
[24]	Lyu, H.; Xie, Z. Chem. Commun. 2022, 58, 8392. doi: 10.1039/D2CC02852B
[25]	Au, Y. K.; Lyu, H.; Quan, Y.; Xie, Z. J. Am. Chem. Soc. 2019, 141, 12855. doi: 10.1021/jacs.9b06204
[26]	Guo, C.; Qiu, Z.; Xie, Z. ACS Catal. 2021, 11, 2134. doi: 10.1021/acscatal.0c05639
[27]	Ge, Y.; Zhang, J.; Qiu, Z.; Xie, Z. Angew. Chem., Int. Ed. 2020, 59, 4851. doi: 10.1002/anie.v59.12
[28]	Ge, Y.; Qiu, Z.; Xie, Z. Acta Chim. Sinica 2022, 80, 432. (in Chinese) doi: 10.6023/A21120597
	(葛懿修, 邱早早, 谢作伟, 化学学报, 2022, 80, 432.) doi: 10.6023/A21120597
[29]	Au, Y. K.; Zhang, J.; Quan, Y.; Xie, Z. J. Am. Chem. Soc. 2021, 143, 4148. doi: 10.1021/jacs.1c00593
[30]	Cao, K.; Huang, Y.; Yang, J.; Wu, J. Chem. Commun. 2015, 51, 7257. doi: 10.1039/C5CC01331C
[31]	Ma, Y. N.; Gao, Y.; Ma, Y.; Wang, Y.; Ren, H.; Chen, X. J. Am. Chem. Soc. 2022, 144, 8371. doi: 10.1021/jacs.2c03031
[32]	Guo, S. T.; Cui, P. F.; Yuan, R. Z.; Jin, G.-X. Chem. Commun. 2021, 57, 2412. doi: 10.1039/D0CC08290B
[33]	Lyu, H.; Quan, Y.; Xie, Z. Angew. Chem., Int. Ed. 2016, 55, 11840. doi: 10.1002/anie.v55.39
[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. doi: 10.1021/acs.joc.1c01804
[35]	Au, Y. K.; Lyu, H.; Quan, Y.; Xie, Z. Chin. J. Chem. 2020, 38, 383. doi: 10.1002/cjoc.v38.4
[36]	Chen, Y.; Au, Y. K.; Quan, Y.; Xie, Z. Sci. China. Chem. 2019, 62, 74. doi: 10.1007/s11426-018-9388-3
[37]	Au, Y. K.; Lyu, H.; Quan, Y.; Xie, Z. J. Am. Chem. Soc. 2020, 142, 6940. doi: 10.1021/jacs.0c02490
[38]	Chen, Y.; Quan, Y.; Xie, Z. Chem. Commun. 2020, 56, 12997. doi: 10.1039/D0CC05207H
[39]	Cheng, B.; Chen, Y.; Zhou, P.; Xie, Z. Chem. Commun. 2022, 58, 629. doi: 10.1039/D1CC05936J
[40]	Li, C. X.; Zhang, H. Y.; Wong, T. Y.; Cao, H. J.; Yan, H.; Lu, C. S. Org. Lett. 2017, 19, 5178. doi: 10.1021/acs.orglett.7b02450
[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. doi: 10.1021/acs.inorgchem.1c02758
[42]	Cui, C. X.; Zhang, J.; Qiu, Z.; Xie, Z. Dalton. Trans. 2020, 49, 1380. doi: 10.1039/C9DT04553H
[43]	Cao, K.; Xu, T. T.; Wu, J.; Jiang, L.; Yang, J. Chem. Commun. 2016, 52, 11446. doi: 10.1039/C6CC06200H
[44]	Lyu, H.; Quan, Y.; Xie, Z. Chem. Eur. J. 2017, 23, 14866. doi: 10.1002/chem.201703006
[45]	Lyu, H.; Zhang, J.; Yang, J.; Quan, Y.; Xie, Z. J. Am. Chem. Soc. 2019, 141, 4219. doi: 10.1021/jacs.9b00302
[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. doi: 10.1002/chem.v26.22
[47]	Qiu, Z.; Quan, Y.; Xie, Z. J. Am. Chem. Soc. 2013, 135, 12192. doi: 10.1021/ja405808t
[48]	Xu, T.-T.; Zhang, C.-Y.; Cao, K.; Wu, J.; Jiang, L.; Li, J.; Li, B.; Yang, J. ChemistrySelect 2017, 2, 3396. doi: 10.1002/slct.201700704
[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. doi: 10.1021/jacs.8b01754
	(b) Cheng, R.; Zhang, J.; Zhang, H.; Qiu, Z.; Xie, Z. Nat. Commun. 2021, 12, 7146. doi: 10.1038/s41467-021-27441-y

过渡金属催化硼-氢键活化合成含硼-杂原子键邻碳硼烷衍生物的研究进展

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

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