溴化亚铜催化合成二甲亚砜叶立德的新方法
收稿日期: 2015-04-07
修回日期: 2015-05-04
网络出版日期: 2015-05-08
基金资助
国家自然科学基金(No. 21272100)资助项目.
Copper(I) Bromide-Catalyzed for the Synthesis of Sulfoxonium Ylides
Received date: 2015-04-07
Revised date: 2015-05-04
Online published: 2015-05-08
Supported by
Project supported by the National Natural Science Foundation of China (No. 21272100).
张宏宇 , 黄靖 , 杨尚东 . 溴化亚铜催化合成二甲亚砜叶立德的新方法[J]. 有机化学, 2015 , 35(9) : 1961 -1965 . DOI: 10.6023/cjoc201504005
A simple and efficient method for the synthesis of substituted sulfoxonium ylides from diazocompounds in dimethyl sulfoxide was developed. It is notable that the reaction employs cheap and harmless copper(I) bromide as catalyst. Moreover, the mild reaction system and a wide range of substrates with high yields make the protocol very practical.
Key words: CuBr; diazocompounds; dimethyl sulfoxide; sulfoxonium ylides
[1] (a) Padwa, A.; Hornbuckle, S. H. Chem. Rev. 1991, 91, 263. (b) Wang, Q.-G.; Deng, X.-M.; Zhu, B.-H.; Ye, L.-W.; Sun, X.-L.; Li, C.-Y.; Zhu, C.-Y.; Shen, Q.; Tang, Y. J. Am. Chem. Soc. 2008, 130, 5408.(c) Li, Y.; Huang, Z.; Xu, P.-F.; Zhang, Y.; Wang, J. Acta Chim. Sinica 2012, 70, 2024 (in Chinese). (李玉叶, 黄重行, 许鹏飞, 张艳, 王剑波, 化学学报, 2012, 70, 2024.)(d) Li, G.; Wang, L.; Huang, Y. Chin. J. Org. Chem. 2013, 33, 1900 (in Chinese). (李公春, 王利叶, 黄有, 有机化学, 2013, 33, 1900.)(e) Ma, M.; Peng, L.; Zhang, X.; Wang, J. Chin. J. Org. Chem. 2005, 25, 408 (in Chinese).(马明, 彭玲玲, 张秀, 王剑波, 有机化学, 2005, 25, 408.) (f) Deng, X.-M.; Cai, P.; Ye, S.; Sun, X.-L.; Liao, W.-W.; Li, K.; Tang, Y.; Wu, Y.-D.; Dai, L.-X. J. Am. Chem. Soc. 2006, 128, 9730.(g) Wang, D.-K.; Dai, L.-X.; Hou, X.-L. Chem. Commun. 1997, 1231. (h) Qu, J.-P.; Xu, Z.-H.; Zhou, J.; Cao, C.-L.; Sun, X.-L.; Dai, L.-X.; Tang, Y. Adv. Synth. Catal. 2009, 351, 308. (i) Ma, M.; Peng, L.; Li, C.; Zhang, X.; Wang, J. J. Am. Chem. Soc. 2005, 127, 15016.(j) Lu, L.-Q.; Zhang, J.-J.; Li, F.; Cheng, Y.; An, J.; Chen, J.-R.; Xiao, W.-J. Angew. Chem., Int. Ed. 2010, 49, 4495.(k) Yang, Q.-Q.; Xiao, C.; Lu, L.; An, J.; Tan, F.; Li, B.-J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 9137.(l) Lu, L.; Chen, J.-R.; Xiao, W.-J. Acc. Chem. Res. 2012, 45, 1278. (m) Chen, Z.; Zhang, J. Chem. Asian J. 2009, 4, 1527.(n) Jiang, Y.; Ma, D. Tetrahedron: Asymmetry 2002, 13, 1033.
[2] (a) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 867.(b) Corey, E. J.; Chaykovsky, M. J.Am. Chem. Soc. 1964, 86, 1640.(c) Corey, E. J.; Chaykovsky, M. Tetrahedron Lett. 1963, 4, 169. (b) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1353.(e) Gololobov, Y.G.; Nesmeyanov, A. N.; Lysenko, V. P.; Boldeskul, I. E. Tetrahedron 1987, 43, 2609. (f) Bernard, A.M.; Frongia, A.; Piras, P.P.; Secci, F.; Spiga, M. Org. Lett. 2005, 7, 4565.(g) Kakei, H.; Sone, T.; Sohtome, Y.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2007, 129, 13410.(h) Yamashita, M.; Okuyama, K.; Kawajiri, T.; Ohta, S. Tetrahedron 2002, 58, 1497
[3] (a) Schomaker, J. M.; Bhattacharjee, S.; Yan, J.; Borhan, B. J. Am. Chem. Soc. 2007, 129, 1996. (b) Hodgson, D. M.; Fleming, M. J.; Xu, Z. Q.; Stanway, S. J. Chem. Commun. 2006, 3226. (c) Molinaro, C.; Bulger, P. G.; Lee, E. E.; Kosjek, B.; Lau, S.; Gauvreau, D.; Howard, M. E.; Wallace, D. J.; O'Shea, P. D. J. Org. Chem. 2012, 77, 2299(d) Luong, H.; Luss-Lusis, E.; Tanoury, G. J.; Nugent, W. A. Eur. J. Org. Chem. 2013, 4238.(e) Mangion, I. K.; Nwamba, I. K.; Shevlin, M.; Huffman, M. A. Org. Lett. 2009, 11, 3566.
[4] Guan, X.-Y.; Liu, Z.-Q.; Huang, H.-X.; Yang, L.-P.; Jian, L.; Hu, W.-H. Synlett 2009, 2183.
[5] (a) Gao, B.-L.; Ma, S.-T.; Liu, Z.-P. Lett. Org. Chem. 2009, 6, 648.(b) Tamura, Y.; Taniguchi, H.; Miyamoto, T.; Tsunekawa, M.; Ikeda, M. J.Org. Chem. 1974, 39, 3519.(c) Wang, D.; Schwinden, M. D.; Radesca, L.; Patel, B.; Kronenthal, D.; Huang, M.-H.; Nugent, W. A. J. Org. Chem. 2004, 69, 1629.
[6] (a) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223.(b) Xiao, Q.; Wang, J.-B. Acta Chim. Sinica 2007, 65, 1733 (in Chinese). (肖卿, 王剑波, 化学学报, 2007, 65, 1733.)(c) Zhu, Y.; Liu, X.; Dong, S.; Zhou, Y.; Li, W.; Lin, L.; Feng, X. Angew. Chem., Int. Ed. 2014, 53, 1636.(d) Ren, L.; Lian, X.-L.; Gong, L.-Z. Chem.-Eur. J. 2013, 19, 3315.(e) Qiu, L.; Guo, X.; Ma, C.; Qiu, H.; Liu, S.; Yang, L. P.; Hu, W. Chem. Commun. 2014, 50, 2196.(f) Qiu, L.; Gao, L.; Tang, J.; Wang, D.; Guo, X.; Liu, S.; Yang, L.; Li, J.; Hu, W. J. Org. Chem. 2014, 79, 4142.(g) Liu, C.-R.; Zhu, B.-H.; Zheng, J.-C.; Sun, X.-L.; Xie, Z.; Tang, Y. Chem. Commun. 2011, 47, 1342.(h) Liu, B.; Zhu, S.-F.; Zhang, W.; Chen, C.; Zhou, Q.-L. J. Am. Chem. Soc. 2007, 129, 5834.
[7] (a) Furukawa, N.; Takahashi, F.; Yoshimura, T.; Oae, S. Tetrahedron Lett. 1977, 18, 3633.(b) Furukawa, N.; Takahashi, F.; Yoshimura, T.; Oae, S. Tetrahedron 1979, 35, 317.
[8] (a) Dost, F.; Gosselck, J. Chem. Ber. 1972, 105, 948. (b) Dost, F.; Gosselck, J. Tetrahedron Lett. 1970, 11, 5091.
[9] (a) Pang, W.; Zhu, S.; Xing, C.; Luo, N.; Jiang, H.; Zhu, S. J. Fluorine Chem. 2008, 129, 343.(b) Moody, C. J.; Taylor, R. J. Tetrahedron Lett. 1988, 29, 6005. (c) Moody, C. J.; Slawin, A. M. Z.; Taylor, R. J.; Williams, D. J. Tetrahedron Lett. 1988, 29, 6009.(d) Moody, C. J.; Taylor, R. J. Tetrahedron 1990, 46, 6525.(e) Suarez, A. I. O.; del Río, M. P.; Remerie, K.; Reek, J. N. H.; de Bruin, B. ACS Catal. 2012, 2, 2046.
[10] (a) Zhu, S.; Zhu, S.; Liao, Y. J. Fluorine Chem. 2004, 125, 1071.(b) Takebayashi, M.; Kashiwada, T.; Hamaguchi, M.; Ibata, T. Chem. Lett. 1973, 809.(c) Ando, W.; Yagihara, T.; Tozune, S.; Imai, I.; Suzuki, J.; Toyama, T.; Nakaido, S.; Migita, T. J. Org. Chem. 1972, 37, 1721.(d) Ando, W.; Yagihara, T.; Tozune, S.; Nakaido, S.; Migita, T. Tetrahedron Lett. 1969, 10, 1979.
/
〈 |
|
〉 |