Nickel-Catalyzed Suzuki-Type Cross Coupling of Fluorinated Alkenyl Boronates with Alkyl Halides
- Corresponding author: Lu Xi, luxi@mail.ustc.edu.cn Fu Yao, fuyao@ustc.edu.cn
Citation: He Shijiang, Pi Jingjing, Li Yan, Lu Xi, Fu Yao. Nickel-Catalyzed Suzuki-Type Cross Coupling of Fluorinated Alkenyl Boronates with Alkyl Halides[J]. Acta Chimica Sinica, ;2018, 76(12): 956-961. doi: 10.6023/A18080333
(a) Gao, B.; Zhao, Y.; Hu, J. Angew. Chem., Int. Ed. 2015, 54, 638. (b) Wu, X.; Xie, F.; Gridnev, I. D.; Zhang, W. Org. Lett. 2018, 20, 1638. (c) Wang, M.; Pu, X.; Zhao, Y.; Wang, P.; Li, Z.; Zhu, C.; Shi, Z. J. Am. Chem. Soc. 2018, 140, 9061. (d) Li, G.; Wang, T.; Fei, F.; Su, Y.-M.; Li, Y.; Lan, Q.; Wang, X.-S. Angew. Chem., Int. Ed. 2016, 55, 3491. (e) Gong, T.-J.; Xu, M.-Y.; Yu, S.-H.; Yu, C.-G.; Su, W.; Lu, X.; Xiao, B.; Fu, Y. Org. Lett. 2018, 20, 570. (f) Zheng, J.; Cai, J.; Lin, J.-H.; Guo, Y.; Xiao, J.-C. Chem. Commun. 2013, 49, 7513. (g) Sha, M.; Zhang, D.; Pan, R.; Xing, P.; Jiang, B. Acta Chim. Sinica 2015, 73, 395(in Chinese). (沙敏, 张丁, 潘仁明, 邢萍, 姜标, 化学学报, 2015, 73, 395.) (h) Gou, B.; Yang, C.; Zhang, L.; Xia, W. Acta Chim. Sinica 2017, 75, 66(in Chinese). (苟宝权, 杨超, 张磊, 夏吾炯, 化学学报, 2017, 75, 66.) (i) Zhang, P.; Lu, L.; Shen, Q. Acta Chim. Sinica 2017, 75, 744(in Chinese). (张盼盼, 吕龙, 沈其龙, 化学学报, 2017, 75, 744.) (j) Wang, J.; Li, F.; Xu, Y.; Wang, J.; Wu, Z.; Yang, C.; Liu, L. Chin. J. Org. Chem. 2018, 38, 1155. (k) Wang, Q.; Gao, K.; Zou, J.; Zeng, R. Chin. J. Org. Chem. 2018, 38, 863(in Chinese). (王清, 高克成, 邹建平, 曾润生, 有机化学, 2018, 38, 863.) (l) Wang, D.; Yuan, Z.; Liu, Q.; Chen, P.; Liu, G. Chin. J. Chem. 2018, 36, 507.
(a) Hu, M.; He, Z.; Gao, B.; Li, L.; Ni, C.; Hu, J. J. Am. Chem. Soc. 2013, 135, 17302. (b) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881. (c) Zhou, N.; Xu, P.; Li, W.; Cheng, Y.; Zhu, C. Acta Chim. Sinica 2017, 75, 60(in Chinese). (周能能, 胥攀, 李伟鹏, 成义祥, 朱成建, 化学学报, 2017, 75, 60.) (d) Rong, J.; Ni, C.; Wang, Y.; Kuang, C.; Gu, Y.; Hu, J. Acta Chim. Sinica 2017, 75, 105(in Chinese). (荣健, 倪传法, 王云泽, 匡翠文, 顾玉诚, 胡金波, 化学学报, 2017, 75, 105.) (e) Sun, X.; Wang, W.; Ma, J.; Yu, S. Acta Chim. Sinica 2017, 75, 115(in Chinese). (孙晓阳, 王文敏, 马晶, 俞寿云, 化学学报, 2017, 75, 115.) (f) Xu, J.; Chen, P.; Ye, J.; Liu, G. Acta Chim. Sinica 2015, 73, 1294(in Chinese). (徐佳斌, 陈品红, 叶金星, 刘国生, 化学学报, 2015, 73, 1294.) (g) Zhao, X.; Li, T.; Tian, M.; Su, Z.; Wei, A.; Lu, K. Chin. J. Org. Chem. 2018, 38, 677. (h) Liu, L.; Huang, D.; Wang, Y.; Wen, L.; Yang, Z.; Su, Y.; Wang, K.; Hu, Y. Chin. J. Org. Chem. 2018, 38, 1469. (i) Liu, Q.; Hu, X. Chin. J. Org. Chem. 2018, 38, 1525. (j) Gu, Y.; Lu, C.; Gu, Y.; Shen, Q. Chin. J. Chem. 2018, 36, 55. (k) Fu, X.-P.; Xiao, Y.-L.; Zhang, X. Chin. J. Chem. 2018, 36, 143. (l) Shi, H.; Lai, B.; Chen, S.; Zhou, X.; Nie, J.; Ma, J.-A. Chin. J. Chem. 2017, 35, 1693.
(a) Okoromoba, O. E.; Han, J.; Hammond, G. B.; Xu, B. J. Am. Chem. Soc. 2014, 136, 14381. (b) Dutheuil, G.; Couve-Bonnaire, S.; Pannecoucke, X. Angew. Chem., Int. Ed. 2007, 46, 1290. (c) Liu, T.-L.; Wu, J. E.; Zhao, Y. Chem. Sci. 2017, 8, 3885. (d) Jakobsche, C. E.; Peris, G.; Miller, S. J. Angew. Chem., Int. Ed. 2008, 47, 6707. (e) Sommer, H.; Fürstner, A. Chem. Eur. J. 2017, 23, 558.
(a) Daubresse, N.; Chupeau, Y.; Francesch, C.; Lapierre, C.; Pollet, B.; Rolando, C. Chem. Commun. 1997, 1489. (b) Chen, C. Y.-C. J. Taiwan Inst. Chem. Eng. 2009, 40, 155. (c) Haidoune, M. B.; Raynaud, I.; O'Connor, N.; Richomme, P.; Mornet, R.; Laloue, M. J. Agric. Food Chem. 1998, 46, 1577. (d) Lin, J.; Toscano, P. J.; Welch, J. T. Proc. Natl. Acad. Sci. U. S. A. 1998, 95, 14020. (e) Van der Veken, P.; Senten, K.; Kertèsz, I.; De Meester, I.; Lambeir, A.-M.; Maes, M.-B.; Scharpé, S.; Haemers, A.; Augustyns, K. J. Med. Chem. 2005, 48, 1768. (f) Liu, Q.; Shen, X.; Ni, C.; Hu, J. Angew. Chem., Int. Ed. 2017, 56, 619. (g) Lu, X.; He, S.-J.; Cheng, W.-M.; Shi, J. Chin. Chem. Lett. 2018, 29, 1001.
(a) Zhang, X.; Cao, S. Tetrahedron Lett. 2017, 58, 375. (b) Novikov, M. A.; Nefedov, O. M. Org. Biomol. Chem. 2018, 16, 4963. (c) Yokota, M.; Fujita, D.; Ichikawa, J. Org. Lett. 2007, 9, 4639. (d) Takachi, M.; Kita, Y.; Tobisu, M.; Fukumoto, Y.; Chatani, N. Angew. Chem., Int. Ed. 2010, 49, 8717. (e) Xu, L.; Zhang, Q.; Xie, Q.; Huang, B.; Dai, J.-J.; Xu, J.; Xu, H.-J. Chem. Commun. 2018, 54, 4406. (f) Zhao, Y.; Jiang, F.; Hu, J. J. Am. Chem. Soc. 2015, 137, 5199. (g) Kojima, R.; Kubota, K.; Ito, H. Chem. Commun. 2017, 53, 10688.
(a) Zhang, X.; Lin, Y.; Zhang, J.; Cao, S. RSC Adv. 2015, 5, 7905. (b) Zell, D.; Dhawa, U.; Müller, V.; Bursch, M.; Grimme, S.; Ackermann, L. ACS Catal. 2017, 7, 4209. (c) Sakaguchi, H.; Uetake, Y.; Ohashi, M.; Niwa, T.; Ogoshi, S.; Hosoya, T. J. Am. Chem. Soc. 2017, 139, 12855. (d) Tan, D.-H.; Lin, E.; Ji, W.-W.; Zeng, Y.-F.; Fan, W.-X.; Li, Q.; Gao, H.; Wang, H. Adv. Synth. Catal. 2018, 360, 1032. (e) Hayashi, S.-i.; Nakai, T.; Ishikawa, N. Chem. Lett. 1980, 9, 935. (f) Zhang, B.; Zhang, X.; Hao, J.; Yang, C. Org. Lett. 2017, 19, 1780. (g) Fuchibe, K.; Mayumi, Y.; Zhao, N.; Watanabe, S.; Yokota, M.; Ichikawa, J. Angew. Chem., Int. Ed. 2013, 52, 7825. (h) Ichitsuka, T.; Fujita, T.; Arita, T.; Ichikawa, J. Angew. Chem., Int. Ed. 2014, 53, 7564. (i) Sakaguchi, H.; Ohashi, M.; Ogoshi, S. Angew. Chem., Int. Ed. 2018, 57, 328. (j) Cong, Z.-S.; Li, Y.-G.; Chen, L.; Xing, F.; Du, G.-F.; Gu, C.-Z.; He, L. Org. Biomol. Chem. 2017, 15, 3863. (k) Xiong, Y.; Huang, T.; Ji, X.; Wu, J.; Cao, S. Org. Biomol. Chem. 2015, 13, 7389. (l) Dai, W.; Shi, H.; Zhao, X.; Cao, S. Org. Lett. 2016, 18, 4284. (m) Yang, L.; Ji, W.-W.; Lin, E.; Li, J.-L.; Fan, W.-X.; Li, Q.; Wang, H. Org. Lett. 2018, 20, 1924. (n) Li, J.; Lefebvre, Q.; Yang, H.; Zhao, Y.; Fu, H. Chem. Commun. 2017, 53, 10299. (o) Xing, B.; Ni, C.; Hu, J. Chin. J. Chem. 2018, 36, 206. (p) Zhang, Z.; Zhou, Q.; Yu, W.; Li, T.; Zhang, Y.; Wang, J. Chin. J. Chem. 2017, 35, 387.
Tian, P.; Feng, C.; Loh, T.-P. Nat. Commun. 2015, 6, 7472.
doi: 10.1038/ncomms8472
(a) Kong, L.; Zhou, X.; Li, X. Org. Lett. 2016, 18, 6320. (b) Wu, J.-Q.; Zhang, S.-S.; Gao, H.; Qi, Z.; Zhou, C.-J.; Ji, W.-W.; Liu, Y.; Chen, Y.; Li, Q.; Li, X.; Wang, H. J. Am. Chem. Soc. 2017, 139, 3537. (c) Ji, W.-W.; Lin, E.; Li, Q.; Wang, H. Chem. Commun. 2017, 53, 5665.
Xie, J.; Yu, J.; Rudolph, M.; Rominger, F.; Hashmi, A. S. K. Angew. Chem., Int. Ed. 2016, 55, 9416.
doi: 10.1002/anie.201602347
Thornbury, R. T.; Toste, F. D. Angew. Chem., Int. Ed. 2016, 55, 11629.
doi: 10.1002/anie.201605651
Zhang, J.; Dai, W.; Liu, Q.; Cao, S. Org. Lett. 2017, 19, 3283.
doi: 10.1021/acs.orglett.7b01430
Hu, J.; Han, X.; Yuan, Y.; Shi, Z. Angew. Chem., Int. Ed. 2017, 56, 13342.
doi: 10.1002/anie.201708224
(a) Lu, X.; Wang, Y.; Zhang, B.; Pi, J.-J.; Wang, X.-X.; Gong, T.-J.; Xiao, B.; Fu, Y. J. Am. Chem. Soc. 2017, 139, 12632. (b) Xu, J.; Ahmed, E.-A.; Xiao, B.; Lu, Q.-Q.; Wang, Y.-L.; Yu, C.-G.; Fu, Y. Angew. Chem., Int. Ed. 2015, 54, 8231. (c) Xu, J.; Fu, Y.; Luo, D.-F.; Jiang, Y.-Y.; Xiao, B.; Liu, Z.-J.; Gong, T.-J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 15300.
(a) Lu, X.; Xiao, B.; Zhang, Z.; Gong, T.; Su, W.; Yi, J.; Fu, Y.; Liu, L. Nat. Commun. 2016, 7, 11129. (b) Lu, X. Ph.D. Dissertation, University of Science and Technology of China, Hefei, 2016(in Chinese). (陆熹, 博士论文, 中国科学技术大学, 合肥, 2016.) (c) Xiao, Y.; Pan, Q.; Zhang, X. Acta Chim. Sinica 2015, 73, 383(in Chinese). (肖玉兰, 潘强, 张新刚, 化学学报, 2015, 73, 383.) (d) Xu, J.; Xiao, B.; Xie, C.-Q.; Luo, D.-F.; Liu, L.; Fu, Y. Angew. Chem., Int. Ed. 2012, 51, 12551.
Lu, X.; Xiao, B.; Liu, L.; Fu, Y. Chem. Eur. J. 2016, 22, 11161.
doi: 10.1002/chem.201602486
Yi, J.; Lu, X.; Sun, Y.-Y.; Xiao, B.; Liu, L. Angew. Chem., Int. Ed. 2013, 52, 12409.
doi: 10.1002/anie.201307069
(a) González-Bobes, F.; Fu, G. C. J. Am. Chem. Soc. 2006, 128, 5360. (b) Zultanski, S. L.; Fu, G. C. J. Am. Chem. Soc. 2013, 135, 624. (c) Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 1340.
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Bz=benzoyl
Bpin=pinacolato boronate
a Isolated yield for 0.2 mmol scale reaction. For X=I, reaction conditions are the same as those for Table 1, Entry 14. For X=Br, reaction conditions are the same as those for Table 1, Entry 19. TEMPO=2, 2, 6, 6-tetramethylpiperidinooxy.