Me3SiCl促进亚铁氰化钾为氰源的α,β-不饱和酮的共轭氢氰化
收稿日期: 2015-01-15
修回日期: 2015-01-27
网络出版日期: 2015-02-05
基金资助
国家自然科学基金(Nos. 21362034, 21162026)、高等学校博士学科点专项科研基金(No. 20136203120005)和甘肃省高等学校科研(No. 2013B-003)资助项目.
Me3SiCl-Promoted Conjugate Hydrocyanation of α,β-Unsaturated Ketones Using Potassium Hexacyanoferrate(II) as Cyanide Source
Received date: 2015-01-15
Revised date: 2015-01-27
Online published: 2015-02-05
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21362034 and 21162026), the Research Fund for the Doctoral Program of Higher Education of China (No. 20136203120005) and the University Scientific Research Project of Gansu Province (No. 2013B-003).
杨靖亚 , 占宝华 , 马奔 , 向现成 , 保云芬 , 李政 . Me3SiCl促进亚铁氰化钾为氰源的α,β-不饱和酮的共轭氢氰化[J]. 有机化学, 2015 , 35(6) : 1286 -1293 . DOI: 10.6023/cjoc201501019
A Me3SiCl-promoted conjugate hydrocyanation of α,β-unsaturated ketones using non-toxic potassium hexacyanoferrate(II) as an eco-friendly cyanide source is described. By "one-pot" procedure, the intermediate, trimethylsilyl cyanide, does not need separation. With 1 mol% Cs2CO3 as catalyst, a variety of aromatic and aliphatic α,β-unsaturated ketones afforded the corresponding β-cyano ketones regioselectivity exclusively. Avoiding the traditional highly toxic cyanide and without separation of the reactive intermediate trimethylsilyl cyanide make this protocol more practical.
[1] For selected examples, see: (a) Nicolaou, K. C.; Stepan, A. F.; Lister, T.; Li, A.; Montero, A.; Tria, G. S.; Turner, C. I.; Tang, Y.; Wang, J.; Denton, R. M.; Edmonds, D. J. J. Am. Chem. Soc. 2008, 130, 13110. (b) Winkler, M.; Knall, A. C.; Kulterer, M. R.; Klempier, N. J. Org. Chem. 2007, 72, 7423.
[2] For selected examples, see: (a) Nazef, N.; Davies, R. D. M.; Greaney, M. F. Org. Lett. 2012, 14, 3720. (b) Utsugi, M.; Kamada, Y.; Miyamoto, H.; Nakada, M. Tetrahedron Lett. 2007, 48, 6868. (c) Peese, K. M.; Gin, D. Y. J. Am. Chem. Soc. 2006, 128, 8734. (d) Rahman, S. M. A.; Ohno, H.; Maezaki, N.; Iwata, C.; Tanaka, T. Org. Lett. 2000, 2, 2893. (e) Fox, M. E.; Li, C.; Marino, J. P.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 5467.
[3] For selected examples, see: (a) Fukuta, Y.; Mita, T.; Fukuda, N.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 6312. (b) Ok, D.; Li, C.; Abbadie, C.; Felix, J. P.; Fisher, M. H.; Garcia, M. L.; Kaczorowski, G. J.; Lyons, K. A.; Martin, W. J.; Priest, B. T.; Smith, M. M.; Williams, B. S.; Wyvratt, M. J.; Parsons, W. H. Bioorg. Med. Chem. Lett. 2006, 16, 1358.
[4] Kurono, N.; Nii, N.; Sakaguchi, Y.; Uemura, M.; Ohkuma, T. Angew. Chem., Int. Ed. 2011, 50, 5541.
[5] Cook, C. E.; Allen, D. A.; Miller, D. B.; Whisnant, C. C. J. Am. Chem. Soc. 1995, 117, 7269.
[6] Nagata, W.; Yoshioka, M.; Murakami, M. J. Am. Chem. Soc. 1972, 94, 4654.
[7] For selected examples, see: (a) Hayashi, M.; Kawabata, H.; Shimono, S.; Kakehi, A. Tetrahedron Lett. 2000, 41, 2591. (b) Iida, H.; Moromizato, T.; Hamana, H.; Matsumoto, K. Tetrahedron Lett. 2007, 48, 2037. (c) Tanaka, Y.; Kanai, M.; Shibasaki, M. Synlett 2008, 2295. (d) Tanaka, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2008, 130, 6072. (e) Yang, J.; Wang, Y.; Wu, S.; Chen, F.-X. Synlett 2009, 3365. (f) Yang, J.; Shen, Y.; Chen, F.-X. Synthesis 2010, 1325. (g) Yang, J.; Chen, F.-X. Chin. J. Chem. 2010, 28, 981. (h) Tanaka, Y.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2010, 132, 8862. (i) Yang, J.; Wu, S.; Chen, F.-X. Synlett 2010, 2725. (j) Zhang, J.; Liu, X.; Wang, R. Chem. Eur. J. 2014, 20, 4911.
[8] For selected examples, see: (a) Ellis, J. E.; Davis, E. M.; Brower, P. L. Org. Process Res. Dev. 1997, 1, 250. (b) Provencher, B. A.; Bartelson, K. J.; Liu, Y.; Foxman, B. M.; Deng, L. Angew. Chem., Int. Ed. 2011, 50, 10565. (c) Kawai, H.; Okusu, S.; Tokunaga, E.; Sato, H.; Shiro, M.; Shibata, N. Angew. Chem., Int. Ed. 2012, 51, 4959.
[9] Wang, Y.-F.; Zeng, W.; Sohail, M.; Guo, J.; Wu, S.; Chen, F.-X. Eur. J. Org. Chem. 2013, 4624.
[10] (a) Lin, S.; Wei, Y.; Liang, F. Chem. Commun. 2012, 48, 9879. (b) Dong, H.-R.; Dong, W.-J.; Li, R.-S.; Hu, Y.-M.; Dong, H.-S.; Xie, Z.-X. Green Chem. 2014, 16, 3454.
[11] Ramesh, S.; Lalitha, A. Acta Chim. Slov. 2013, 60, 689.
[12] (a) Li, Z.; Liu, C.; Zhang, Y.; Li, R.; Ma, B.; Yang, J. Synlett 2012, 23, 2567. (b) Li, Z.; Yin, J.; Li, T.; Wen, G.; Shen, X.; Yang, J. Tetrahedron 2014, 70, 5619.
[13] Schareina, T.; Zapf, A.; Beller, M. Chem. Commun. 2004, 1388.
[14] For reviews, see: (a) Anbarasan, P.; Schareina, T.; Beller, M. Chem. Soc. Rev. 2011, 40, 5049. (b) Wang, L.; Zhao, W.; Duan, Z. Prog. Chem. 2010, 22, 1964 (in Chinese). (王丽丽, 赵伟宁, 段征, 化学进展, 2010, 22, 1964.)
[15] For selected examples, see: (a) Mariampillai, B.; Alliot, J.; Li, M.; Lautens, M. J. Am. Chem. Soc. 2007, 129, 15372. (b) Schareina, T.; Zapf, A.; Mägerlein, W.; Müller, N.; Beller, M. Chem. Eur. J. 2007, 13, 6249. (c) Ren, Y.; Liu, Z.; Zhao, S.; Tian, X.; Wang, J.; Yin, W.; He, S. Catal. Commun. 2009, 10, 768. (d) Schareina, T.; Jackstell, R.; Schulz, T.; Zapf, A.; Cotté, A.; Gotta, M.; Beller, M. Adv. Synth. Catal. 2009, 351, 643. (e) Gerber, R.; Oberholzer, M.; Frech, C. M. Chem. Eur. J. 2012, 18, 2978. (f) Modak, A.; Mondal, J.; Bhaumik, A. Green Chem. 2012, 14, 2840. (g) Senecal, T. D.; Shu, W.; Buchwald, S. L. Angew. Chem., Int. Ed. 2013, 52, 10035. (h) Giachi, G.; Frediani, M.; Oberhauser, W.; Lamaty, F.; Martinez, J.; Colacino, E. ChemSusChem 2014, 7, 919.
[16] Schareina, T.; Zapf, A.; Mägerlein, W.; Müller, N.; Beller, M. Synlett 2007, 555.
[17] Zhu, Y.-Z.; Cai, C. Synth. Commun. 2008, 38, 2753.
[18] (a) Ren, Y.; Yan, M.; Zhao, S.; Sun, Y.; Wang, J.; Yin, W.; Liu, Z. Tetrahedron Lett. 2011, 52, 5107. (b) Ren, Y.; Dong, C.; Zhao, S.; Sun, Y.; Wang, J.; Ma, J.; Hou, C. Tetrahedron Lett. 2012, 53, 2825.
[19] For selected examples, see: (a) Li, Z.; Shi, S.; Yang, J. Synlett 2006, 2495. (b) Cheng, Y.-N.; Duan, Z.; Yu, L.; Li, Z.; Zhu, Y.; Wu, Y. Org. Lett. 2008, 10, 901. (c) Yan, G.; Kuang, C.; Zhang, Y.; Wang, J. Org. Lett. 2010, 12, 1052. (d) Li, Z.; Ma, Y.; Xu, J.; Shi, J.; Cai, H. Tetrahedron Lett. 2010, 51, 3922. (e) Li, Z.; Tian, G.; Ma, Y. Synlett 2010, 2164. (f) Zhao, Z.; Li, Z. Eur. J. Org. Chem. 2010, 5460. (g) Hu, X.; Ma, Y.; Li, Z. J. Organomet. Chem. 2012, 705, 70. (h) Li, Z.; Xu, J.; Niu, P.; Liu, C.; Yang, J. Tetrahedron 2012, 68, 8880. (i) Hu, X.; Li, H.; Yang, J.; Li, Z. Synlett 2014, 25, 1786. (j) Li, Z.; Wen, F.; Yang, J. Chin. J. Chem. 2014, 32, 1251.
[20] Li, Z.; Zhang, Y.; Wen, F.; Yin, J.; Zheng, H.; Li, H.; Yang, J. J. Chem. Res. 2013, 37, 601.
[21] Li, Z.; Li, R.; Zheng, H.; Wen, F.; Li, H.; Yin, J.; Yang, J. J. Braz. Chem. Soc. 2013, 24, 1739.
[22] Samson, M.; Vandewalle, M. Synth. Commun. 1978, 8, 231.
[23] Cabirol, F. L.; Lim, A. E. C.; Hanefeld, U.; Sheldon, R. A.; Lyapkalo, I. M. J. Org. Chem. 2008, 73, 2446.
[24] Li, Z.; Sun, Y.; Song, G.; Zhou, J. CN 101250197, 2008 [Chem. Abstr. 2008, 149, 356032].
[25] (a) Chen, J.; Spear, S. K.; Huddleston, J. G.; Rogers, R. D. Green Chem. 2005, 7, 64. (b) Chen, G.; Weng, J.; Zheng, Z.; Zhu, X.; Cai, Y.; Cai, J.; Wan, Y. Eur. J. Org. Chem. 2008, 3524.
[26] (a) Landini, D.; Maia, A.; Montanari, F. J. Am. Chem. Soc. 1978, 100, 2796. (b) Parker, A. J. Chem. Rev. 1969, 69, 1.
[27] (a) Sammis, G. M.; Jacobsen, E. N. J. Am. Chem. Soc. 2003, 125, 4442. (b) Sammis, G. M.; Danjo, H.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 9928. (c) Mita, T.; Sasaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 514. (d) Mazet, C.; Jacobsen, E. N. Angew. Chem. Int. Ed. 2008, 47, 1762.
[28] (a) Gawronski, J.; Wascinska, N.; Gajewy, J. Chem. Rev. 2008, 108, 5227. (b) Benaglia, M.; Guizzetti, S.; Pignataro, L. Coord. Chem. Rev. 2008, 252, 492. (c) Rendler, S.; Oestreich, M. Synthesis 2005, 1727.
[29] Prakash, G. K. S.; Vaghoo, H.; Panja, C.; Surampudi, V.; Kultyshev, R.; Mathew, T.; Olah, G. A. Proc. Natl. Acad. Sci. U. S. A. 2007, 104, 3026.
[30] Berryman, K. A.; Doherty, A. M.; Edmunds, J. J.; Patt, W. C.; Plummer, M. S.; Repine, J. T. US 5691373, 1997 [Chem. Abstr. 1997, 128, 48214].
[31] Davey, W.; Tivey, D. J. J. Chem. Soc. 1958, 1230.
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