Acenaphthoimidazole N-Heterocyclic Carbene Palladium ComplexesCatalyzed Cyanation Reactions in Aqueous Accelerated byMicrowave Irradiation

doi:10.6023/cjoc201506029

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (11): 2389-2392.DOI: 10.6023/cjoc201506029 Previous Articles Next Articles

Notes

微波促进苊并咪唑氮杂环卡宾钯化合物催化的水相氰基化反应

蒋晓军^a, 申雅靓^b, 刘泽龙^b, 吕绪良^a, 涂涛^b

a 解放军理工大学野战工程学院南京 210007;
b 复旦大学化学系上海 200433

收稿日期:2015-06-24 修回日期:2015-07-09 发布日期:2015-08-17
通讯作者: 吕绪良, 涂涛 E-mail:xllu1957@126.com;taotu@fudan.edu.cn
基金资助:
教育部博士点基金(No. 20130071110032)、上海市带头学科(No. B108)及复旦大学卓学资助项目.

Acenaphthoimidazole N-Heterocyclic Carbene Palladium ComplexesCatalyzed Cyanation Reactions in Aqueous Accelerated byMicrowave Irradiation

Jiang Xiaojun^a, Shen Yajing^b, Liu Zelong^b, Lü Xuliang^a, Tu Tao^b

a College of Field Engineering, PLA University of Science and Technology, Nanjing 210007;
b Department of Chemistry, Fudan University, Shanghai 200433

Received:2015-06-24 Revised:2015-07-09 Published:2015-08-17
Supported by:
Project supported by the Research Fund of Doctoral Program, Ministry of Education (No. 20130071110032), the Shanghai Leading Academic Discipline Project (B108) and the Department of Chemistry Fudan University.

1. Acenaphthoimidazole N-Heterocyclic Carbene Palladium ComplexesCatalyzed Cyanation Reactions in Aqueous Accelerated byMicrowave Irradiation.PDF(812KB)

Abstract

In the presence of acenaphthoimidazole N-heterocyclic carbene palladium complexes, cyanation of aryl bromides by non-toxic and inexpensive potassium hexacyanoferrate (II) as cyanide source in water has been investigated under microwave conditions. Both electron-donating and electron-withdrawing groups attached to the substrates show unobvious effects on the transformation and produce the corresponding products in good to excellent yields within few minutes, which demonstrate the practicability and environmentally friendliness of the new developed protocol.

Key words: cyanation, N-heterocyclic carbene, microwave assistant, palladium, aqueous phase

Cite this article

Jiang Xiaojun, Shen Yajing, Liu Zelong, Lü Xuliang, Tu Tao. Acenaphthoimidazole N-Heterocyclic Carbene Palladium ComplexesCatalyzed Cyanation Reactions in Aqueous Accelerated byMicrowave Irradiation[J]. Chin. J. Org. Chem., 2015, 35(11): 2389-2392.

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[1] Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D. Pharmaceutical Substances: Syntheses, Patents, Applications, 4th ed., Georg Thieme, Stuttgart, 2001.
[2] (a) Larock, R. C. Comprehensive Organic Transformations, VCH, New York, 1989, p. 819.(b) Grundmann, C. In Houben-Weyl: Methoden der Organischen Chemie, 4th ed., Ed.: Falbe, J., Georg Thieme Verlag, Stuttgart, 1985, Vol. E5, p. 1313.(c) Hagedorn, F.; Gelbke, H.-P. In Ullmanns Encyklopadie der Technischen Chemie, 4th ed., Eds.: Bartholomé, E.; Biekert, E.; Hellmann, H.; Ley, H.; Weigert, W. M.; Weise, E., Verlag Chemie, Weinheim, 1979, Vol. 17, p. 333.(d) Ferri, C. Reaktionen der Organischen Chemie, Georg Thieme Verlag, Stuttgart, 1978, p. 571.(e) Kurtz, P. In Houben Weyl: Methoden Der Organischen Chemie, 4th ed., Ed.: Muller, E., Georg Thieme Verlag, Stuttgart, 1952, Vol. 8, p. 265.
[3] Takagi, K.; Okamoto, T.; Sakakibara, Y.; Oka, S. Chem. Lett. 1973, 471.
[4] (a) Sekiya, A.; Ishikawa, N. Chem. Lett. 1975, 277.(b) Takagi, K.; Okamoto, T.; Sakakibara, Y.; Ohno, A.; Oka, S.; Hayama, N. Bull. Chem. Soc. Jpn. 1975, 48, 3298.(c) Akita, Y.; Shimazaki, M.; Ohta, A. Synthesis. 1981, 974.(d) Prochazka, M.; Siroky, M. Collect. Czech. Chem. Commun. 1983, 48, 1765.(e) Sato, N.; Suzuki, M. J. Heterocycl. Chem. 1987, 24, 1371.(f) Tanji, K.; Higashino, T. Heterocycles 1990, 30, 435.(g) Takagi, K.; Sasaki, K.; Sakakibara, Y. Bull. Chem. Soc. Jpn. 1991, 64, 1118
[5] Dalton, J. R.; Regen, S. L. J. Org. Chem. 1979, 44, 4443.
[6] Chatani, N.; Hanafusa, T. J. Org. Chem. 1986, 51, 4714.
[7] Nair, V.; Purdy, D. F.; Sells, T. B. J. Chem. Soc., Chem. Commun. 1989, 878.
[8] (a) Tschaen, D. M.; Desmond, R.; King, A. O.; Fortin, M. C.; Pipik, B.; King, S.; Verhoeven, T. R. Synth. Commun. 1994, 24, 887.(b) Gundersen, L. L. Acta Chem. Scand. 1996, 50, 58.
[9] (a) Schareina, T.; Zapf, A.; Beller, M. Chem. Commun. 2004, 1388.(b) Merz, V.; Weith, W. Chem. Ber. 1877, 10, 746.
[10] Gedye, R.; Smith, F.; Westaway, K.; Ali, H.; Baldisera, L.; Laberge, L.; Rousell, J. Tetrahedron Lett. 1986, 27, 279.
[11] (a) Li, L.; Pan, Z.; Duan, X.; Liang, Y. Synlett. 2006, 2094.(b) Velmathi, S.; Leadbeate, N. Tetrahedron Lett. 2008, 49, 4693.(c) Chen, G.; Weng, J.; Zheng, Z.; Zhu, X.; Cai, Y.; Cai, J.; Wan, Y. Eur. J. Org. Chem. 2008, 22, 3524.(d) Ren, Y. L.; Wang, W.; Zhao, S.; Tian, X.; Wang, J.; Yin, W.; Cheng, L. Tetrahedron Lett. 2009, 50, 4595.(e) Fang, K.; Wen, W.; Chen, L.; Peng, L. Chin. J. Org. Chem. 2013, 33, 2559 (in Chinese).(柯方, 吴雯, 林晨, 李鹏, 有机化学,2013, 33, 2559.)
[12] Matthew, N.; Hopkinson, C. R.; Michael, S.; Glorius, F. Nat. Chem. 2014, 510, 485.
[13] (a) Tu, T.; Feng, X.; Wang, Z.; Liu, X. Dalton Trans. 2010, 39, 10598.(b) Tu, T.; Mao, H.; Herbert, C.; Xu, M.; Dötzb, K. H. Chem. Commun. 2010, 46, 7796.(c) Tu, T.; Fang, W.; Jiang, J. Chem. Commun. 2011, 47, 12358.(d) Tu, T.; Sun, Z.; Fang, W.; Xu, M.; Zhou, Y. Org. Lett. 2012, 14, 4250.(e) Fang, W.; Deng, Q.; Xu, M.; Tu, T. Org. Lett. 2013, 15, 3678.(f) Jiang, J.; Zhu, H.; Shen, Y.; Tu, T. Org. Chem. Front. 2014, 1, 1172.
[14] Alagiri, K.; Prabhu, K. R. Tetrahedron 2011, 67, 8544.
[15] Zhou, W.; Wang, K.; Wang, J. Adv. Synth. Catal. 2009, 351, 1378.
[16] Grossman, O.; Gelman, D. Org. Lett. 2006, 8, 1189.
[17] Mino, T.; Koizumi, T.; Shibuya, M.; Hirai, K.; Sakamoto, M.; Fujita, T. Heterocycles 2011, 83, 163.
[18] Karthikeyan, J.; Parthasarathy, K.; Cheng, C. Chem. Commun. 2011, 47, 10461.
Qin, W.; Yasuike, S.; Kakusawa, N.; Kurita, J. J. Organomet. Chem. 2008, 693, 2949.

微波促进苊并咪唑氮杂环卡宾钯化合物催化的水相氰基化反应

Acenaphthoimidazole N-Heterocyclic Carbene Palladium ComplexesCatalyzed Cyanation Reactions in Aqueous Accelerated byMicrowave Irradiation

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