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2012 , Vol. 32 >Issue 05: 934 - 938

DOI: https://doi.org/10.6023/cjoc1110242

研究简报

无溶剂条件下LiNTf2 催化的醛和酮的非手性硅氰化反应研究

  • 王宏社 ,
  • 曾君娥
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  • 宝鸡文理学院化学化工系 陕西省植物化学重点实验室 宝鸡 721013

收稿日期: 2011-10-24

  修回日期: 2011-12-20

  网络出版日期: 2012-01-11

基金资助

陕西省教育厅科研计划(No. 09JK332)和宝鸡文理学院重点(No. ZK1053)资助项目.

收起

Solvent-Free Achiral Cyanosilylation of Aldehydes and Ketones Catalyzed by LiNTf2

  • Wang Hongshe ,
  • Zeng June
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  • Shaanxi Key Laboratory for Phytochemistry, Department of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji 721013

Received date: 2011-10-24

  Revised date: 2011-12-20

  Online published: 2012-01-11

Supported by

Project supported by the Scientific Research Program of Shaanxi Provincial Education Deparment (No. 09JK332) and the Key Project of Baoji University of Arts and Sciences (No. ZK1053).

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摘要

以LiNTf2 为催化剂, 在无溶剂条件下, 醛或酮与三甲基氰硅烷(TMSCN)室温发生加成反应, 得到相应的α-氰基硅醚. 该法操作简便、反应条件温和、收率高、催化剂易回收和可以重复使用.

关键词： LiNTf2; 醛; 酮; 硅氰化反应; 无溶剂

本文引用格式

王宏社 , 曾君娥 . 无溶剂条件下LiNTf2 催化的醛和酮的非手性硅氰化反应研究[J]. 有机化学, 2012 , 32(05) : 934 -938 . DOI: 10.6023/cjoc1110242

Abstract

An efficient method for the addition of trimethylsilyl cyanide (TMSCN) to various aldehydes and ketones has been described using LiNTf2 (1 mol%) as a catalyst at room temperature under solvent-free conditions. The advantages of this method are easy work-up, mild reaction conditions, high yields and the catalyst exhibited remarkable reusable activity.

Key words： LiNTf2; aldehyde; ketone; cyanosilylation; solvent-free

参考文献

[1] Breuer, M.; Ditrich, K.; Habicher, T.; Hauer, B.; Kebeler, M.;Sturmer, R.; Zelinski, T. Angew. Chem., Int. Ed. 2004, 43, 788.  

[2] Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 8106.  

[3] Luo, H. Chin. J. Org. Chem. 2011, 31, 1 (in Chinese).(罗海南, 有机化学, 2011, 31, 1.)

[4] Gregory, R. H. J. Chem. Rev. 1999, 99, 3649.  

[5] Majhi, A.; Kim, S. S.; Kim, H. S. Appl. Organomet. Chem. 2008,22, 407.  

[6] Heydari, A.; Mamani, L. Appl. Organomet. Chem. 2008, 22, 12.  

[7] Song, J. J.; Gallou, F.; Reeves, J. T.; Tan, Z.; Yee, N. K.; Senanayake,C. H. J. Org. Chem. 2006, 71, 1273.  

[8] Kurono, N.; Yamaguchi, M.; Suzuki, K.; Ohkuma, T. J. Org.Chem. 2005, 70, 6530.  

[9] Cho, W. K.; Lee, J. K.; Kang, S. M.; Chi, Y. S.; Lee, H.-S.; Choi, I.S. Chem. Eur. J. 2007, 13, 6351.

[10] Pourmousavi, S. A.; Salahshornia, H. Bull. Korean Chem. Soc.2011, 32, 1575.  

[11] Lacour, M.-A.; Rahier, N. J.; Taillefer, M. Chem. Eur. J. 2011, 17,12276.  

[12] Park, B. Y.; Ryu, K. Y.; Park, J. H.; Lee, S. Green Chem. 2009, 11,946.  

[13] Kim, S. S.; Rajagopal, G. Synthesis 2007, 215.  

[14] kantam, M. L.; Mahendar, K.; Sreedhar, B.; Kumar, K. V.; Choudary,B. M. Synth. Commun. 2008, 38, 3919.  

[15] Thirupathi, B.; Patil, M. K.; Reddy, B. M. Appl. Catal. A: Gen.2010, 384, 147.  

[16] Wang, X.-L.; Wang, Y.-X.; Bian, Z.-X. Acta Chim. Sinica 2007,65, 1670 (in Chinese).(王晓丽, 王艳学, 边占喜, 化学学报, 2007, 65, 1670.)

[17] Azizi, N.; Saidi, M. R. J. Organomet. Chem. 2003, 688, 283.  

[18] Geng, X.-H.; Zhou, H.; Chen, P.-R.; Xu, Q. Chin. J. Org. Chem.2008, 28, 1157 (in Chinese).(耿晓红, 周辉, 陈沛然, 徐青, 有机化学, 2008, 28, 1157.)

[19] Wang, W.; Liu, X.; Lin, L.; Feng, X. Eur. J. Org. Chem. 2010,4751.

[20] Zhang, Z.; Wang, Z.; Zhang, R.; Ding, K. Angew. Chem., Int. Ed.2010, 49, 6746.  

[21] Kurono, N.; Arai, K.; Uemura, M.; Ohkuma, T. Angew. Chem., Int.Ed. 2008, 47, 6643.  

[22] Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2005, 127, 5384.  

[23] Liu, X.; Qin, B.; Zhou, X.; He, B.; Feng, X. J. Am. Chem. Soc.2005, 127, 12224.  

[24] Dang, D.; Wu, P.; He, C.; Xie, Z.; Duan, C. J. Am. Chem. Soc.2010, 132, 14321.  

[25] Yuan, Y.-B.; Nie, J. Chin. J. Org. Chem. 2004, 24, 857 (in Chinese).(袁余斌, 聂进, 有机化学, 2004, 24, 857.)

[26] Wang, L.-Q.; Nie, J.; Li, X.-Y.; Zhang, Z.-B.; Yin, F. Chin. J. Org.Chem. 2004, 24, 778 (in Chinese).(王丽琼, 聂进, 李小永, 张正波, 尹飞, 有机化学, 2004, 24,778.)

[27] Asao, N.; Aikawa, H. J. Org. Chem. 2006, 71, 5249.  

[28] Sweis, R. F.; Schramm, M. P.; Kozmin, S. A. J. Am. Chem. Soc.2004, 126, 7442.  

[29] Earle, M. J.; Hakala, U.; McAuley, B. J.; Nieuwenhuyzen, M.; Ramani,A.; Seddon, K. R. Chem. Commun. 2004, 1368.  

[30] Grau, F.; Heumann, A.; Dunach, E. Angew. Chem., Int. Ed. 2006,45, 7285.  

[31] Wang, H.-S.; Zhao, L.-F. Chin. J. Org. Chem. 2005, 25, 869 (inChinese).(王宏社, 赵立芳, 有机化学, 2005, 25, 869.)

[32] Wang, H.; Zeng, J. Chin. J. Org. Chem. 2010, 30, 1072 (in Chinese).(王宏社, 曾君娥, 有机化学, 2010, 30, 1072.)

[33] Cossy, J.; Bellosta, V.; Hamoir, C.; Desmurs, J.-R. TetrahedronLett. 2002, 43, 7083.  
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