Copper-Catalyzed Enantioselective Aminoboration of Styrenes with Chiral Sulfoxide Phosphine Ligand
- Corresponding author: Liao Jian, jliao@cib.ac.cn
Citation: Zhang Yongling, Wang Min, Cao Peng, Liao Jian. Copper-Catalyzed Enantioselective Aminoboration of Styrenes with Chiral Sulfoxide Phosphine Ligand[J]. Acta Chimica Sinica, ;2017, 75(8): 794-797. doi: 10.6023/A17040144
(a) Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents, Academic Press, London, 1988; (b) Miyaura, N.; Suzuki, A. Chem. Rev.1995, 95, 2457; (c) Davison, M.; Hughes, A. K.; Marder, T. B.; Wade, K. Contemporary Boron Chemistry, RSC, Cambridge, U. K., 2000; (d) Boronic Acids, 2nd ed.; Ed.: Hall, D. G., Wiley-VCH, Weinheim, Germany, 2011.
(a) Ishiyama, T.; Matsuda, N.; Miyaura, N.; Suzuki, A. J. Am.Chem. Soc. 1993, 115, 11018; (b) Ishiyama, T.; Matsuda, N.; Murata, M.; Ozawa, F.; Suzuki, A.; Miyaura, N. Organometallics 1996, 15, 713; (c) Lesley, G.; Nguyen, P.; Taylor, N. J.; Marder, T. B. Organometallics 1996, 15, 5137; (d) Ishiyama, T.; Yamamoto, M.; Miyaura, N. Chem.Commun. 1996, 2073; (e) Ishiyama, T.; Yamamoto, M.; Miyaura, N. Chem.Commun. 1997, 689; (f) Thomas, R. L.; Souza, F. E. S.; Marder, T. B. J. Chem. Soc., Dalton Trans. 2001, 1650; (g) Yang, F.-Y.; Cheng, C.-H. J. Am. Chem. Soc. 2001, 123, 761; (h) Burks, H. E.; Kliman, L. T.; Morken, J. P. J. Am.Chem. Soc. 2009, 131, 9134; (i) Kliman, L. T.; Mlynarski, S. N.; Morken, J. P. J. Am. Chem. Soc. 2009, 131, 13210; (j) Iwadate, N.; Suginome, M. J. Am. Chem. Soc. 2010, 132, 2548; (k) Coombs, J. R.; Haeffner, F.; Kliman, L. T.; Morken, J. P. J. Am. Chem. Soc. 2013, 135, 11222; (l) Coombs, J. R.; Zhang, L.; Morken, J. P. J. Am.Chem. Soc. 2014, 136, 16140; For review, see: Ishiyama, T.; Ishida, K.; Miyaura, N. Tetrahedron 2001, 57, 9813 and references therein.
Selected examples, see: (a) Adams, C. J.; Baber, R. A.; Batsanov, A. S.; Bramham, G.; Charmant, J. P.; Haddow, M. F.; Howard, J. A.; Lam, W. H.; Lin, Z.; Marder, T. B.; Norman, N. C.; Orpen, A. G. Dalton Trans. 2006, 1370; (b) Obligacion, J. V.; Chirik, P. J. Org. Lett.2013, 15, 2680; (c) Obligacion, J. V.; Chirik, P. J. J. Am.Chem. Soc. 2013, 135, 19107. (d) Zhang, L.; Peng, D.; Leng, X.; Huang, Z. Angew. Chem., Int. Ed. 2013, 52, 3676; (e) Cao, Y.; Zhang, Y.; Zhang, L.; Zhang, D.; Leng, X.; Huang, Z. Org. Chem. Front.2014, 1, 1101; (f) Chen, J.; Xi, T.; Lu, Z.Org. Lett. 2014, 16, 6452; (g) Chen, J.; Xi, T.; Ren, X.; Cheng, B.; Guo, J.; Lu, Z. Org. Chem. Front. 2014, 1, 1306; (h) Zhang, L.; Zuo, Z.; Leng, X.; Huang, Z. Angew. Chem., Int. Ed. 2014, 53, 2696; (i) Zhang, L.; Zuo, Z.; Wan, X.; Huang, Z. J. Am. Chem. Soc. 2014, 136, 15501; (j) Guo, J.; Chen, J.; Lu, Z. Chem. Commun. 2015, 51, 5725; (k) Zhang, L.; Huang, Z. J. Am. Chem. Soc. 2015, 137, 15600; (l) Zhang, H.; Lu, Z. ACS Catal. 2016, 6, 6596; (m) Zuo, Z.; Huang, Z. Org. Chem. Front. 2016, 3, 434; (n) Zuo, Z.; Yang, J.; Huang, Z. Angew. Chem., Int.Ed. 2016, 55, 10839; (o) Xi, T.; Lu, Z. ACS Catal. 2017, 7, 1181.
(a) Suginome, M.; Matsuda, T.; Yoshimoto, T.; Ito, Y. Org. Lett.1999, 1, 1567; (b) Suginome, M.; Shirakura, M.; Yamamoto, A. J.Am. Chem. Soc. 2006, 128, 14438; (c) Ely, R. J.; Morken, J. P. J. Am. Chem. Soc. 2010, 132, 2534.
(a) Bloch, R. Chem. Rev. 1998, 98, 1407; (b) Ramadhar, T. R.; Batey, R. A. Synthesis 2011, 1321; (c) Yus, M.; González-Gómez, J. C.; Foubelo, F. Chem. Rev. 2013, 113, 5595.
(a) Matsuda, N.; Hirano, K.; Satoh, T.; Miura, M. J. Am.Chem. Soc. 2013, 135, 4934; (b) Sakae, R.; Matsuda, N.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2014, 16, 1228; (c) Parra, A.; Amenos, L.; Guisan-Ceinos, M.; Lopez, A.; Garcia Ruano, J. L.; Tortosa, M. J. Am. Chem. Soc. 2014, 136, 15833; (d) Sakae, R.; Hirano, K.; Miura, M. J. Am. Chem. Soc.2015, 137, 6460; (e) Sakae, R.; Hirano, K.; Satoh, T.; Miura, M. Angew.Chem., Int. Ed. 2015, 54, 613; (f) Kato, K.; Hirano, K.; Miura, M. Angew. Chem., Int. Ed. 2016, 55, 14400; (g) Nishikawa, D.; Hirano, K.; Miura, M. Org. Lett.2016, 18, 4856; (h) Shi, M. Chem. Commun. 2016, 52, 5273.
(a) Chen, B.; Cao, P.; Yin, X.; Liao, Y.; Jiang, L.; Ye, J.; Wang, M.; Liao, J. ACS Catal. 2017, 7, 2425; (b) Jia, T.; Cao, P.; Wang, B.; Lou, Y.; Yin, X.; Wang, M.; Liao, J. J. Am.Chem. Soc. 2015, 137, 13760; (c) Jia, T.; Cao, P.; Wang, D.; Lou, Y.; Liao, J. Chem. Eur. J.2015, 21, 4918.
Metro, T. X.; Appenzeller, J.; Pardo, D. G.; Cossy, J. Org. Lett. 2006, 8, 3509.
doi: 10.1021/ol061133d
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Reaction conditions: 10 wt% Pd/C wetted with ca. 55% water (0.04 mmol), (S)-3a (0.4 mmol) in MeOH (3.0 mL) under hydrogen by balloon. The suspension was stirred at 25 ℃ for 12 h.