膦氧导向钯催化邻碳硼烷Heck类型的官能团化反应
收稿日期: 2021-03-06
修回日期: 2021-04-16
网络出版日期: 2021-05-08
基金资助
国家自然科学基金(21772023); 国家自然科学基金(21901041)
Phosphine Oxide-Directed Palladium-Catalyzed Heck-Type Functionalization of o-Carboranes
Received date: 2021-03-06
Revised date: 2021-04-16
Online published: 2021-05-08
Supported by
National Natural Science Foundation of China(21772023); National Natural Science Foundation of China(21901041)
连凌翔 , 尹静怡 , 林彩霞 , 叶克印 , 袁耀锋 . 膦氧导向钯催化邻碳硼烷Heck类型的官能团化反应[J]. 有机化学, 2021 , 41(8) : 3249 -3255 . DOI: 10.6023/cjoc202103015
The selective functionalization of o-carboranes is a popular topic in carborane chemistry. o-Carborane has been widely used in aggregation-induced luminescent materials, nonlinear luminescent materials and other function materials due to its special 3D-aromaticity. The π conjugated systems-tethered o-carboranes could further broaden its applications in the field of luminescent materials. Herein, we have developed a palladium-catalyzed Heck-type mono-alkenylation of o-carboranes featuring phosphine oxide as the directing group.
Key words: palladium; Heck reaction; carborane; B—H activation
[1] | (a) Liu, L. J.; Mak T, C. W.; Zang, S. Q. Chin. J. Chem. 2021, 39, 81. |
[1] | (b) Kolel-Veetil, M. K.; Beckham, H. W.; Keller, T. M. Chem. Mater. 2004, 16, 3162. |
[1] | (c) Gao, Y.; Cui, P. F.; Aznarez, F.; Jin, G. X., Chem.-Eur. J. 2018, 24, 10357. |
[1] | (d) Armstrong, A. F.; Valliant, J. F. Dalton Trans. 2007, 38, 4240. |
[2] | (a) Cui, P.-F.; Lin, Y. J.; Li, Z. H.; Jin, G.-X. J. Am. Chem. Soc. 2020, 142, 8532. |
[2] | (b) Guo, S.-T.; Cui, P.-F.; Yuan, R.-Z.; Jin, G.-X. Chem. Commun. 2021, 57, 2412. |
[3] | (a) Xiong, H. J.; Li, Y. R.; Ye, H. H.; Huang, G.; Zhou, D. F.; Huang, Y. B. J. Mater. Chem. B 2020, 8, 10309. |
[3] | (b) Zhang, J.; Liu, K.; Liu, Z. S.; Wang, Z. L.; Hua, C. X.; Liu, T. H.; Fang, Y. ACS Appl. Mater. Inter. 2021, 13, 5625. |
[3] | (c) Yao, Z. J.; Jin, Y.-X.; Deng, W.; Liu, Z.-J. Inorg. Chem. 2021, 60, 2756. |
[4] | Sarosi, M.-B.; Neumann, W.; Lybrand, T. P.; Hey-Hawkins, E. J. Chem. Inf. Model. 2017, 57, 2056. |
[5] | (a) Zhang, J; Xie, Z. W. Chin. J. Chem. 2018, 36, 1041. |
[5] | (b) Chan, T L; Xie, Z. Chem. Sci. 2018, 9, 2284. |
[5] | (c) Guo, J. X.; Liu, D. Q.; Zhang, J. H.; Zhang, J. J.; Miao, Q.; Xie, Z. W. Chem. Commun. 2015, 51, 12004. |
[5] | (d) Tu, D. S.; Cai, S. Z.; Fernandez, C.; Ma, H. L.; Wang, X.; Wang, H.; Ma, C. Q.; Yan, H.; Lu, C. S.; An, Z. F. Angew Chem. Int. Ed. 2019, 58, 9129. |
[5] | (e) Wei, X.; Zhu, M. J.; Cheng, Z.; Lee, M.; Yan, H.; Lu, C. S.; Xu, J. J. Angew. Chem. Int. Ed. 2019, 58, 3162. |
[6] | (a) Wang, Z. J.; Zhao, J. W.; Muddassir, M.; Guan, R. F.; Tao, S. L. Inorg. Chem. 2021, 60, 4705. |
[6] | (b) Li, X.; Zhou, Q.; Zhu, M.; Chen, W.; Wang, B. B.; Sha, Y.; Yan, H. Chem.-Asian J. 2021, 7, 757. |
[6] | (c) Ochi, J.; Tanaka, K.; Chujo, Y. Angew. Chem. Int. Ed. 2020, 25, 9841. |
[6] | (d) Nishino, K.; Tanaka, K.; Chujo, Y. Asian J. Org. Chem. 2019, 12, 2228. |
[7] | (a) Chen, Y.; Au, Y. K.; Quan, Y. J.; Xie, Z. W. Sci. China Chem. 2019, 62, 74. |
[7] | (b) Zheng, F. R.; Leung, T. F.; Chan, K. W.; Sung, H. H. Y.; Williams, I. D.; Xie, Z. W.; Jia, G. C. Chem. Commun. 2016, 52, 10767. |
[7] | (c) Lyu, H. R.; Quan, Y. J.; Xie, Z. W. Angew. Chem. Int. Ed. 2015, 54, 10623. |
[7] | (d) Zhao, D.; Zhang, J. J.; Xie, Z. W. Chem.-Eur. J. 2015, 21, 10334. |
[8] | (a) Kürti, L.; Czakó, B. Strategic Applications of Named Reactions in Organic Synthesis:Background and Detailed Mecnisms, Elsevier Academic Press, Burlington, 2007,p. 196. |
[8] | (b) Huang, X. L.; Teng, S. H.; Chi, Y. R.; Xu, W. Q.; Pu, M. P.; Wu, Y. D.; Zhou, J. S. Angew. Chem. Int. Ed. 2020, 60, 2828. |
[8] | (c) Peng, X. P.; Yang, Y.; Luo, B. L.; Wen, S. J.; Huang, P. Adv. Syn. Catal. 2021, 363, 222. |
[8] | (d) Ju, B. H.; Chen, S. G.; Kong, W. Q. Org. Lett. 2019, 21, 9343. |
[8] | (e) Zhou, L. X.; Shi, Y. X.; Zhu, X. Y.; Zhang, P. Tetrahedron Lett. 2019, 60, 2005. |
[8] | (f) Xie, J.-Q.; Liang, R.-X.; Jia, Y.-X. Chin. J. Chem. 2021, 3, 710. |
[8] | (g) Yang, P.; Xu, R.-Q.; Zheng, C.; You, S.-L. Chin. J. Chem. 2020, 3, 235. |
[8] | (h) Liu, C. X.; Liu, G. Y.; Zhao, H. K. Chin. J. Chem. 2016, 10, 1048. |
[9] | (a) Wen, Z. K.; Zhao, Z. K.; Wang, N. J.; Chen, Z. L.; Chao, J. B.; Feng, L. H. Org. Lett. 2019, 21, 9545. |
[9] | (b) Bettadapur, K. R.; Sherikar, M. S.; Lanke, V.; Prabhu, K. R. Asian J. Org. Chem. 2018, 7, 1338. |
[10] | Grimes, R. N. Carboranes, 3rd ed., Elsevier, Oxford, 2016. |
[11] | (a) Wu, J.; Cao, K.; Xu, T.-T.; Zhang, X.-J.; Jiang, L.; Yang, J. X.; Huang, Y. W. RSC Adv. 2015, 5, 91683. |
[11] | (b) Lyu, H. R.; Quan, Y. J.; Xie, Z. W. Angew. Chem. Int. Ed. 2015, 54, 10623. |
[11] | (c) Zhang, C. Y.; Wang, Q.; Tian, S.; Zhang, J. W.; Li, J. Y.; Zhou, L.; L, J. Org. Biomol. Chem. 2020, 18, 4723. |
[11] | (d) Wang, Q.; Tian, S.; Zhang, C. Y.; Li, J. W.; Wang, Z. X.; Du, Y. M.; Zhou, L.; L, J. Org. Lett. 2019, 21, 8018. |
[12] | (a) Quan, Y. J.; Xie, Z. W. J. Am. Chem. Soc. 2014, 136, 15513. |
[12] | (b) Quan, Y. J.; Xie, Z. W. Angew. Chem. Int. Ed. 2016, 55, 1295. |
[12] | (c) Lyu, H. R.; Quan, Y. J.; Xie, Z. W. Angew. Chem. Int. Ed. 2016, 128, 12019. |
[12] | (d) Lyu, H. R.; Quan, Y. J.; Xie, Z. W. J. Am. Chem. Soc. 2016, 138, 12727. |
[12] | (e) Lyu, H. R.; Quan, Y. J.; Xie, Z. W. Chem.-Eur. J. 2017, 23, 14866. |
[12] | (f) Baek, Y.; Kim, S. H.; Son, J.-Y.; Lee, K. Y.; Kim, D. W.; Lee, P. H. ACS Catal. 2019, 9, 10418. |
[13] | (a) Xu, T.-T.; Cao, K.; Zhang, C.-Y.; Wu, J.; Ding, L.-F.; Yang, J. X. Org. Lett. 2019, 21, 9276. |
[13] | (b) Xu, T.-T.; Cao, K.; Zhang, C.-Y.; Wu, J.; Jiang, L. H.; Yang, J. X. Chem. Commun. 2018, 54, 13603. |
[13] | (c) Liang, Y.-F.; Yang, L.; Jei, B. B.; Kuniyila, R.; Ackermann, L. Chem. Sci. 2020, 11, 10764. |
[13] | (d) Lyu, H. R.; Zhang, J.; Yang, J. T.; Quan, Y. J.; Xie, Z. W. J. Am. Chem. Soc. 2019, 141, 4219. |
[14] | Lian, L. X.; Lin, C. X.; Yu, Y.; Ye, K.-Y.; Yuan Y. F. Tetrahedron Lett. 2020, 61, 152625. |
[15] | Popescu, A.-R.; Laromaine, A.; Teixidor, F.; Sillanpää, R.; Kivekäs, R.; Llambias, J. I.; Viñas, C. Chem.-Eur. J. 2011, 17, 4429. |
/
〈 |
|
〉 |