OALib Journal期刊
ISSN: 2333-9721
费用:99美元
|
|
|
离子液体中钯催化合成cis-1,2-二卤代-1,7-辛二烯的反应研究有机化学
DOI: 10.6023/cjoc201401017, PP. 1148-1153
Keywords: 离子液体,钯催化,炔卤,5-己烯-1-醇,cis-1,2-二卤代烯烃
Abstract:
发展了一种以PdBr2为催化剂,以[Bmim]X/HXaq为溶剂,炔卤与5-己烯-1-醇进行交叉偶联反应的新方法,以中等及优良的产率(73%~94%)合成了系列cis-1,2-二卤代-1,7-辛二烯衍生物.反应表现出较高的区域选择性和立体选择性.并且该偶联反应合成途径简捷、反应条件温和,可为cis-1,2-二卤代烯烃类化合物的合成提供简便的途径.
References
[1] | (a) Guinchard, X.; Roulland, E. Synlett 2011, 2779.
|
[2] | (a) Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450.
|
[3] | (c) Ruan, J.; Xiao, J. Acc. Chem. Res. 2011, 44, 614.
|
[4] | (e) Butkevich, A. N.; Meerpoel, L.; Stansfield, I.; Angibaud, P.; Corbu, A.; Cossy, J. Org. Lett. 2013, 15, 3840.
|
[5] | (a) Poss, C. S.; Rychnovsky, S. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 3360.
|
[6] | (c) Paqutte, L. A.; Hofferberth, J. E. J. Org. Chem. 2003, 68, 2266.
|
[7] | Yokota, M.; Toyota, M.; Ihara, M. Chem. Commun. 2003, 422.
|
[8] | (b) Novikov, Y. Y.; Sampson, P. J. Org. Chem. 2005, 70, 10247
|
[9] | (b) Tan, Z.; Negishi, E. Angew. Chem., Int. Ed. 2006, 45, 762.
|
[10] | (a) Chiappe, C.; Capraro, D.; Conte, V.; Pieraccini, D. Org. Lett. 2001, 3, 1061.
|
[11] | (c) Lemay, A. B.; Vulic, K. S.; Ogilvie, W. W. J. Org. Chem. 2006, 71, 3615.
|
[12] | (e) Liu, J.; Li, W.; Wang, C.; Li, Y.; Li, Z. Tetrahedron Lett. 2011, 52, 4320.
|
[13] | (d) Li, J.; Yang, S.; Huang, L.; Chen, H.; Jiang, H. RSC Adv. 2013, 3, 11529.
|
[14] | (e) Li, J.; Yang, S.; Jiang, H.; Wu, W.; Zhao, J. J. Org. Chem. 2013, 78, 12477.
|
[15] | (b) Brummond, K. M.; Chen, D. Org. Lett. 2005, 7, 3473.
|
[16] | (d) Mukai, C.; Hara, Y.; Miyashita, Y.; Inagaki, F. J. Org. Chem. 2007, 72, 4454.
|
[17] | (b) Kerber, W. D.; Gagné, M. R. Org. Lett. 2005, 7, 3379.
|
[18] | (d) Selander, N.; Kipke, A.; Sebelius, S.; Szabó, K. J. J. Am. Chem. Soc. 2007, 129, 13723.
|
[19] | (a) Huang, J.; Zhou, L.; Jiang, H. Angew. Chem., Int. Ed. 2006, 45, 1945.
|
[20] | (c) Yang, S; Jiang, H.; Li, Y.; Chen, H.; Luo, W.; Xu, Y. Tetrahedron 2008, 64, 2930.
|
[21] | (e) Li, J.; Yang, S. Chin. J. Org. Chem. 2013, 33, 2407 (in Chinese).
|
[22] | (f) Li, J.; Yang, S.; Wu, W.; Qi, C.; Deng, Z.; Jiang, H. Tetrahedron 2014, 70, 1516.
|
[23] | Ma, S.; Yu, Z. Angew. Chem., Int. Ed. 2003, 42, 1955.
|
[24] | Park, S.; Kazlauskas, R. J. J. Org. Chem. 2001, 66, 8395.
|
[25] | (b) Cosner, C. C.; Helquist, P. Org. Lett. 2011, 13, 3564.
|
[26] | Gibtner, T.; Hampel, F.; Gisselbrecht, J.-P.; Hirsch, A. Chem. Eur. J. 2002, 68, 408
|
[27] | (b) Kutsumura, N.; Niwa, K.; Saito, T. Org. Lett. 2010, 12, 3316.
|
[28] | (d) Everson, D. A.; Jones, B. A.; Weix, D. J. J. Am. Chem. Soc. 2012, 134, 6146.
|
[29] | (b) Xi, Z.; Song, Q.; Chen, J.; Guan, H.; Li, P. Angew. Chem., Int. Ed. 2001, 40, 1913.
|
[30] | (d) Wei, J.; Wang, Z.; Zhang, W.-X.; Xi, Z. Org. Lett. 2013, 15, 1222.
|
[31] | (a) Vanbrunt, M. P.; Ambenge, R. O.; Weinreb, S. M. J. Org. Chem. 2003, 68, 3323.
|
[32] | (a) Zeng, X.; Hu, Q.; Qian, M.; Negishi, E. J. Am. Chem. Soc. 2003, 125, 13636.
|
[33] | (c) Poulsen, T. B.; Dickmeiss, G.; Overgaard, J.; J?rgensen, K. A. Angew. Chem., Int. Ed. 2008, 47, 4687.
|
[34] | (b) Bellina, F.; Colzi, F.; Mannina, L.; Rossi, R.; Viel, S. J. Org. Chem. 2003, 68, 10175.
|
[35] | (d) Ho, M. L.; Flynn, A. B.; Ogilvie, W. W. J. Org. Chem. 2007, 72, 977.
|
[36] | (a) Ochiai, O.; Oshima, K.; Masaki, Y. Chem. Lett. 1994, 871.
|
[37] | (b) Chen, Z.; Jiang, H.; Li, Y.; Qi, C. Chem. Commun. 2010, 46, 8049.
|
[38] | (c) Chen, X.; Kong, W.; Cai, H.; Kong, L.; Zhu, G. Chem. Commun. 2011, 47, 2164.
|
[39] | (a) Buezo, N. D.; Manchen?, O. G.; Carretero, J. C. Org. Lett. 2000, 2, 1451.
|
[40] | (c) Oh, C. H.; Gupta, A. K.; Park, D. I.; Kim, N. Chem. Commun. 2005, 5670.
|
[41] | (a) Widenhoefer, R. A.; Stengone, C. N. J. Org. Chem. 1999, 64, 8681.
|
[42] | (c) Feducia, J. A.; Campbell, A. N.; Doherty, M. Q.; Gagne, M. R. J. Am. Chem. Soc. 2006, 128, 13290.
|
[43] | (a) Wasserscheid, P.; Sesing, M.; Korth, W. Green Chem. 2002, 4, 134.
|
[44] | (b) Vincenzo C., Angelo N., Antonio, M. J. Org. Chem. 2007, 72, 2596.
|
[45] | (b) Yang, S.; Jiang, H.; Chen, H.; Xu, Y.; Luo, W. Synth. Commun. 2007, 37, 2121.
|
[46] | (d) Wu, W.; Jiang, H. Acc. Chem. Res. 2012, 45, 1736.
|
[47] | (李建晓, 杨少容, 有机化学, 2013, 33, 2407.)
|
[48] | (g) Li, J.; Yang, S.; Wu, W.; Jiang, H. Chem. Commun. 2014, 50, 1381.
|
[49] | Huddleston, J. G.; Willauer, H. D.; Swatloski, R. P.; Visser, A. E.; Rogers, R. D. Chem. Commun. 1998, 1765;
|
[50] | Branco, L. C.; Rosa, J. N.; Ramos, J. J. M.; Afonso, C. A. M. Chem. Eur. J. 2002, 8, 3671.
|
[51] | Chum, H. L.; Koch, V. R.; Miller, L. L.; Osteryoung, R. A. J. Am. Chem. Soc. 1975, 97, 3264.
|
Full-Text
|
|
Contact Us
service@oalib.com QQ:3279437679 
WhatsApp +8615387084133
|
|