Chinese Journal of Organic Chemistry >
Zeolite Immobilized Copper Catalyzed Conjugate Borylation of α,β-Unsaturated Compounds in Aqueous Media
Received date: 2020-11-11
Revised date: 2020-11-17
Online published: 2021-02-22
Supported by
National Natural Science Foundation of China(21774029); Natural Science Foundation of Hubei Province(2019CFB237); Natural Science Foundation of Hubei Province(2019CFB354); Young and Middle-Aged Science and Technology Innovation Team Project in Higher Education Institutions of Hubei Province(T201816); Natural Science Foundation of Xiaogan City(XGKJ201910047); Natural Science Foundation of Xiaogan City(XGKJ2020010053); Chutian Scholar" Program of Hubei Province; High-Level Master's Thesis Cultivation Project of Hubei Engineering University
An eco-friendly zeolite immobilized copper catalyzed cojugate borylation of α,β-unsaturated compounds which was accomplished in aqueous media under mild conditions was reported. This method provided a direct and efficient pathway to achieve an important class of β-borylated compounds. Desired products were obtained in good to excellent yields with broad substrate scope. The advantages of this newly developed method include operational simplicity, mild conditions, good functional group tolerance and recyclability of catalyst. Remarkably, this zeolite supported copper catalyst could be recovered easily by simple centrifugation and reused for seven times without any significant decrease of catalytic activity.
Feng Yan , Lijie Zhou , Biao Han , Yaoyao Zhang , Bojie Li , Liansheng Wang , Lei Zhu . Zeolite Immobilized Copper Catalyzed Conjugate Borylation of α,β-Unsaturated Compounds in Aqueous Media[J]. Chinese Journal of Organic Chemistry, 2021 , 41(5) : 2074 -2081 . DOI: 10.6023/cjoc202011017
| [1] | (a) Burkhardt, E. R.; Matos, K. Chem. Rev. 2006, 106, 2617. |
| [1] | (b) Crudden, C. M.; Glasspoole, B. W.; Lata, C. J. Chem. Commun. 2009, 45, 6704. |
| [1] | (c) Yang, J.; Deng, M.; Yu, T. Chin. J. Org. Chem. 2013, 33, 693. (in Chinese). |
| [1] | (杨军, 邓敏智, 于涛, 有机化学, 2013, 33, 693.) |
| [1] | (d) Huang, H.; Lin, H.; Wang, M.; Liao, J. Acta Chim. Sinica 2020, 78, 1229. (in Chinese). |
| [1] | (黄浩, 林华鑫, 王敏, 廖建, 化学学报, 2020, 78, 1229.) |
| [1] | (e) Wang, G.; Gan, Y.; Liu, Y. Chin. J. Chem. 2018, 36, 916. |
| [2] | Lennox, A. J. J.; Lloyd-Jones, G. C. Chem. Soc. Rev. 2014, 43, 412. |
| [3] | Muncipinto, G.; Moquist, P. N.; Schreiber, S. L.; Schaus, S. E. Angew. Chem., Int. Ed. 2011, 50, 8172. |
| [4] | Ripin, D. H. B.; Cai, W.; Brenek, S. J. Tetrahedron Lett. 2000, 41, 5817. |
| [5] | Miura, T.; Nishida, Y.; Morimoto, M.; Murakami, M. J. Am. Chem. Soc. 2013, 135, 11497. |
| [6] | Matteson, D. S. J. Org. Chem. 2013, 78, 10009. |
| [7] | Shimizu, M. Angew. Chem., Int. Ed. 2011, 50, 5998. |
| [8] | Cho, C. S.; Ohe, T.; Uemura, S. J. Organomet. Chem. 1995, 49, 221. |
| [9] | Coeffard, V.; Moreau, X.; Thomassigny, C.; Greck, C. Angew. Chem., Int. Ed. 2013, 52, 5684. |
| [10] | Smoum, R.; Rubinstein, A.; Dembitsky, V. M.; Srebnik, M. Chem. Rev. 2012, 112, 4156. |
| [11] | (a) Kuang, Z.; Chen, H.; Yan, J.; Yang, K.; Lan, Y.; Song, Q. Org. Lett. 2018, 20, 5153. |
| [11] | (b) Kuang, Z.; Li, B.; Song, Q. Chem. Commun. 2018, 54, 34. |
| [11] | (c) Gao, G.; Kuang, Z.; Song, Q. Org. Chem. Front. 2018, 5, 2249. |
| [12] | Johnson, K. M. S. Curr. Opin. Invest. Drugs 2010, 11, 455. |
| [13] | Beenen, M. A.; An, C.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 6910. |
| [14] | Cvek, B. Drug Future 2012, 37, 561. |
| [15] | (a) Stavber, G.; ?asar, Z. ChemCatChem 2014, 6, 2162. |
| [15] | (b) Liu, Q.; Tian, B.; Tian, P.; Tong, X.; Lin, G.-Q. Chin. J. Org. Chem. 2015, 35, 1. (in Chinese). |
| [15] | (刘强, 田兵, 田平, 童晓峰, 林国强, 有机化学, 2015, 35, 1.) |
| [15] | (c) Liu, Y.; Zhang, W. Chin. J. Org. Chem. 2016, 36, 2249. (in Chinese). |
| [15] | (刘媛媛, 张万斌, 有机化学, 2016, 36, 2249.) |
| [16] | Bonet, A.; Gulyás, H.; Koshevoy, I. O.; Estevan, F.; Sanaú, M.; úbeda, A.; Fernández, E. Chem.-Eur. J. 2010, 16, 6382. |
| [17] | Bell, N. J.; Cox, A. J.; Cameron, N. R.; Evans, J. S. O.; Marder, T. B.; Duin, M. A.; Cornelis J.; Elsevier, C. J.; Baucherel, X.; Tullochc, A. A. D.; Tooze, R. P. Chem. Commun. 2004, 16, 1854. |
| [18] | Hirano, K.; Yorimitsu, H.; Oshima, K. Org. Lett. 2007, 9, 5031. |
| [19] | Shiomi, T.; Adachi, T.; Toribatake, K.; Zhou, L.; Nishiyama, H. Chem. Commun. 2009, 40, 5987. |
| [20] | Kajiwara, T.; Terabayashi, T.; Yamashita, M.; Nozaki, K. Angew. Chem., Int. Ed. 2008, 47, 6606. |
| [21] | Huang, X.; Hu, J.; Wu, M.; Wang, J.; Peng, Y.; Song, G. Green Chem. 2018, 20, 255. |
| [22] | Ito, H.; Yamanaka, H.; Tateiwa, J.-I.; Hosomi, A. Tetrahedron Lett. 2000, 41, 6821. |
| [23] | Takahashi, K.; Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2001, 625, 47. |
| [24] | (a) Mun, S.; Lee, J.-E.; Yun, J. Org. Lett. 2006, 8, 4887. |
| [24] | (b) Lee, J.-E.; Yun, J. Angew. Chem., Int. Ed. 2007, 47, 145. |
| [25] | O'Brien, J. M.; Lee, K.-S.; Hoveyda, A. H. J. Am. Chem. Soc. 2010, 132, 10630. |
| [26] | Solé, C.; Tatla, A.; Mata, J. A.; Whiting, A.; Gulyás, H.; Fernández, E. Chem.-Eur. J. 2011, 17, 14248. |
| [27] | (a) Gao, M.; Thorpe, S. B.; Santos, W. L. Org. Lett. 2009, 11, 3478. |
| [27] | (b) Chen, I.-H.; Yin, L.; Itano, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2009, 131, 11664. |
| [27] | (c) Mlynarski, S. N.; Schuster, C. H.; Morken, J. P. Nature 2014, 505, 386. |
| [27] | (d) Dewhurst, R. D.; Marder, T. B. Nat. Chem. 2014, 6, 279. |
| [28] | Thorpe, S. B.; Calderone, J. A.; Santos, W. L. Org. Lett. 2012, 14, 1918. |
| [29] | Stavber, G.; ?asar, Z. ChemCatChem 2014, 6, 2162. |
| [30] | (a) Kobayashi, S.; Xu, P.; Endo, T.; Ueno, M.; Kitanosono, T. Angew. Chem., Int. Ed. 2012, 51, 12763. |
| [30] | (b) Zhu, L.; Kitanosono, T.; Xu, P.; Kobayashi, S. Chem. Commun. 2015, 51, 11685. |
| [30] | (c) Zhu, L.; Kitanosono, T.; Xu, P.; Kobayashi, S. Beilstein J. Org. Chem. 2015, 11, 2007. |
| [31] | (a) Li, B.; Wang, L.; Qin, C.; Zhu, L. Catal. Commun. 2016, 86, 23. |
| [31] | (b) Zhu, L.; Wang, L.-S.; Li, B.; Fu Q.; Zhang, C.-P.; Li, W. Chem. Commun. 2016, 52, 6371. |
| [31] | (c) Zhu, L.; Li, B.; Wang, S.; Wang, W.; Wang, L.; Ding, L.; Qin, C. Polymers 2018, 10, 385. |
| [31] | (d) Wang, W.; Li, B.-J.; Xiao, Z.-F.; Yan, F.; Wei, P.-R.; Wang, L.-S.; Zhu, L. J. Chin. Chem. Soc. 2018, 65, 81. |
| [31] | (e) Wang, W.; Xiao, Z.; Huang, C.; Zheng, K.; Luo, Y.; Dong, Y.; Shen, Z.; Li, W.; Qin, C. Polymers 2019, 11, 1417. |
| [32] | Gawande, M. B.; Goswami, A.; Felpin, F.-X.; Asefa, T.; Huang, X.; Silva, R.; Zou, X.; Zboril, R.; Varma, R. S. Chem. Rev. 2016, 116, 3722. |
| [33] | Zhou, X.-F.; Sun, Y.-Y.; Wu, Y.-D.; Dai, J.-J.; Xu, J.; Huang, Y.; Xu, H.-J. Tetrahedron 2016, 72, 5691. |
| [34] | Wen, W.; Han, B.; Yan, F.; Ding, L.; Li, B.; Wang, L.; Zhu, L. Nanomaterials 2018, 8, 326. |
| [35] | Anastas, P.; Eghbali, N. Chem. Soc. Rev. 2010, 39, 301. |
| [36] | (a) Brezicki, G.; Kammert, J. D.; Gunnoe, T. B.; Paolucci, C.; Davis, R. J. ACS Catal. 2019, 9, 5308. |
| [36] | (b) Vanelderen, P.; Snyder, B. E. R.; Tsai, M.-L.; Hadt, R. G.; Vancauwenbergh, J.; Coussens, O.; Schoonheydt, R. A.; Sels, B. F.; Solomon, E. I. J. Am. Chem. Soc. 2015, 137, 6383. |
| [36] | (c) Wu, J.-F.; Gao, X.-D.; Wu, L.-M.; Wang, W. D.; Yu, S.-M.; Bai, S. ACS catal. 2019, 9, 8677. |
| [37] | Blasco, T.; Boronat, M.; Concepción, P.; Corma, A.; Law, D.; Vidal- Moya, J. A. Angew. Chem., Int. Ed. 2007, 46, 3938. |
| [38] | Moglie, Y.; Buxaderas, E.; Mancini, A.; Alonso, F.; Radivoy, G. ChemCatChem 2019, 11, 1487. |
| [39] | Garnier, T.; Sakly, R.; Danel, M.; Chassaing, S.; Pale, P. Synthesis 2017, 49, 1223. |
| [40] | Kuhn, P.; Pale, P.; Sommer, J.; Louis, B. J. Phys. Chem. C 2009, 113, 2903. |
| [41] | Zhou, L.; Li, S.; Su, Y.; Li, B.; Deng, F. Solid State Nucl. Magn. Reson. 2015, 66~ 67 , 29. |
| [42] | Isegawa, M.; Sameera, W. M. C.; Sharma, A. K.; Kitanosono, T.; Kato, M.; Kobayashi, S.; Morokuma, K. ACS Catal. 2017, 7, 5370. |
| [43] | (a) Singh, P.; Bhardwaj, A. J. Med. Chem. 2010, 53, 3707. |
| [43] | (b) Ravikumar, K. S.; Sinha, S.; Chandrasekaran, S. J. Org. Chem. 1999, 64, 5841. |
| [43] | (c) Berti, F.; Bincoletto, S.; Donati, I.; Fontanive, G.; Fregonesea, M.; Benedetti, F. Org. Biomol. Chem. 2011, 9, 1987. |
| [43] | (d) Barbero, M.; Bazzi, S.; Cadamuro, S.; Dughera, S.; Magistris, C.; Smarraa, A.; Venturello, P. Org. Biomol. Chem. 2011, 9, 2192. |
/
| 〈 |
|
〉 |