Advances in Investigation of Ullmann Reaction Accelerated by Microwave Irradiation

doi:10.6023/cjoc201210023

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (08): 1668-1673.DOI: 10.6023/cjoc201210023 Previous Articles Next Articles

Reviews

微波加速Ullmann反应的研究

肖尚友, 朱俊, 穆小静, 李正华

重庆大学化学化工学院重庆 40030

收稿日期:2012-10-15 修回日期:2013-02-20 发布日期:2013-02-22
通讯作者: 肖尚友 E-mail:xsycqu@yahoo.com.cn
基金资助:
国家自然科学基金(No. 20805060)资助项目.

Advances in Investigation of Ullmann Reaction Accelerated by Microwave Irradiation

Xiao Shangyou, Zhu Jun, Mu Xiaojing, Li Zhenghua

College of Chemistry and Chemical Engineering, Chongqing University, Chongqing 400030

Received:2012-10-15 Revised:2013-02-20 Published:2013-02-22
Supported by:
Project supported by the National Natural Science Foundation of China (No. 20805060).

The Ullmann reaction has been extensively applied in the synthesis of organic intermediates, especially in the formation of carbon-carbon bond, carbon-oxygen bond, carbon-sulfur bond and carbon-nitrogen bond. It has been demonstrated that microwave irradiation can obviously accelerate the Ullmann reaction and improve the yields, so the application of microwave in the Ullmann reaction has caught increasing attention in recent years. The application of microwave in the Ullmann reaction and the progresses in the formation of carbon-carbon bond, carbon-oxygen bond, carbon-sulfur bond and carbon-nitrogen bond are reviewed in this paper.

Key words: Ullmann reaction, microwave, synthesis, review

Cite this article

Xiao Shangyou, Zhu Jun, Mu Xiaojing, Li Zhenghua. Advances in Investigation of Ullmann Reaction Accelerated by Microwave Irradiation[J]. Chin. J. Org. Chem., 2013, 33(08): 1668-1673.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
[2] Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
[3] Suresh, S.; Gulotty, R. J.; Bales, S. E.; Inbasekaran, M. N.; Chartier, M. A.; Cummins, C.; Smith, D. W. Adv. Polym. Sci. 2003. 18, 5111.
[4] Qi, C. Z.; Sun, X. D.; Lu, C. Y.; Yang, J. Z.; Wu, H. J.; Zhang, X. M. J. Organomet. Chem. 2009, 18, 2912.
[5] Hanoun, J. P.; Galy, J. P.; Tenaglia, A. Synth. Commun. 1995, 25, 2443.
[6] Palomo, C.; Oiarbide, M.; López, R.; Gómez-Bengoa, E. Chem. Commun. 1998, 2091.
[7] Gedye, R.; Smith, F.; Westaway, K.; Ali, L.; Baldisera, L.; Laberge, L.; Rouseu, J. Tetrahedron Lett. 1986, 27, 279.
[8] Gabriel, C.; Gabriel, S.; Grant, E. H.; Halstead, B. S. J.; Mingos, D. M. P. Chem. Soc. Rev. 1998, 27, 213.
[9] Mingos, D. M. P.; Baghurst, D. R.; Tilden, L. Chem. Soc. Rev. 1991, 20, 1.
[10] Razzaq, T.; Kremsner, J. M.; Kappe, C. O. J. Org. Chem. 2008, 73, 6321.
[11] Baghurst, D. R.; Mingos, D. M. P.; J. Chem. Soc., Chem. Commun. 1992, 674.
[12] Roy. I.; Gupta. M. V. Tetrahedron 2003, 59, 5431.
[13] Hashim, J.; Glasnov, T. N.; Kremsner, J. M.; Kappe, C. O. J. Org. Chem. 2006, 71, 1707.
[14] Hashim, J.; Kappe, C. O. Adv. Synth. Catal. 2007, 349, 2353.
[15] Hajipour, A. R.; Karami, K.; Tavakoli, G.; Pirisedigh, A. J. Organomet. Chem. 2011, 696, 819.
[16] Arvela, R. K.; Leadbeater, N. E.; Torenius, H. M.; Tye, H. Org. Biomol. Chem. 2003, 1, 1119.
[17] Mehmood, A.; Devine, W. G.; Leadbeater, N. E. Top. Catal. 2010, 53, 1073.
[18] Appukkuttan, P.; Dehaen, W.; Van der Eycken, E. Eur. J. Org. Chem. 2003, 4713.
[19] Leadbeater, N. E.; Marco, M.; Tominack, B. J. Org. Lett. 2003, 5, 3919.
[20] Shook, B. C.; Chakravarty, D.; Jackson, P. F. Tetrahedron Lett. 2009, 50, 1013.
[21] He, H.; Wu, Y. J. Tetrahedron Lett. 2003, 44, 3445.
[22] D’Angelo, N. D.; Peterson, J. J.; Booker, S. K.; Fellows, I.; Dominguez, C.; Hungate, R.; Reider, P. J.; Kim, T. S. Tetrahedron Lett. 2006, 47, 5045.
[23] Zhu, X.-H.; Chen, G.; Ma, Y.; Song, H.-C; Xu, Z.-L.; Wan, Y.-Q. Chin. J. Org. Chem. 2007, 27, 546 (in Chinese).
(朱新海, 陈功, 马彦, 宋化灿, 许遵乐, 万一千, 有机化学, 2007, 27, 546.)
[24] Lan, Z.-L.; Lv, Y.; Xie, Y.-Y.; Liu, Z.; Xie, L.-Q. Chin. J. Appl. Chem. 2002, 19, 346 (in Chinese).
(兰支利, 吕研, 谢永耀, 刘准, 谢庆兰, 应用化学, 2002, 19, 346.)
[25] Benaskar, F.; Engels, V.; Patil, N.; Rebrov, E. V.; Meuldijk, J.; Hessel, V.; Hulshof, L. A.; Jefferson, D. A.; Schouten, J. C.; Wheatley, A. E. H. Tetrahedron Lett. 2010, 51, 248.
[26] Engels, V.; Benaskar, F.; Patil, N.; Rebrov, E. V.; Hessel, V.; Hulshof, L. A.; Jefferson, D. A.; Vekemans, J. A. J. M.; Karwal, S.; Schouten, J. C. Org. Process Res. Dev. 2010, 14, 644.
[27] Pellon, R. F.; Martin, A.; Mesa, M.; Docampo, M. L.; Gomez, V. J. Chem. Res. 2006, 527.
[28] Wu, Y. J.; He, H. Synlett 2003, 1789.
[29] Bagley, M. C.; Dix, M. C.; Fusillo, V. Tetrahedron Lett. 2009, 50, 3661.
[30] Bagley, M. C.; Davis, T.; Dix, M. C.; Fusillo, V.; Pigeaux, M.; Rokicki, M. J.; Kipling, D. J. Org. Chem. 2009, 74, 8336.
[31] Mugnaini, C.; Manetti, F.; Este, J. A.; Clotet-Codina, I.; Maga, G.; Cancio, R.; Botta, M.; Corelli, F. Bioorg. Med. Chem. Lett. 2006, 16, 3541.
[32] Vera-Luque, P.; Alajarín, R.; Alvarez-Builla, J.; Vaquero, J. J. Org. Lett. 2006, 8, 415.
[33] Liu, Y.-Y.; Tao, L.; Feng, G.-R. Chin. J. Org. Chem. 2008, 28, 1278 (in Chinese).
(刘影英, 陶兰, 冯国仁, 有机化学, 2008, 28, 1278.)
[34] Colacino, E.; Villebrun, L.; Martinez, J.; Lamaty, F. Tetrahedron 2010, 66, 3730.
[35] Pabba, C.; Wang, H. J.; Mulligan, S. R.; Chen, Z. J.; Stark, T. M.; Gregg, B. T. Tetrahedron Lett. 2005, 46, 7553.
[36] Bueno, M. A.; Silva, L.; Corrêa, A. G. J. Braz. Chem. Soc. 2008, 19, 1264.
[37] Meng, F.; Wang, C.; Xie, J.; Zhu, X.; Wan, Y. Appl. Organomet. Chem. 2011, 25, 341.
[38] Wu, Y. J.; He, H.; L. Heureux, A. Tetrahedron Lett. 2003, 44, 4217.
[39] Röttger, S.; Sjöberg, P. J. R.; Larhed, M. J. Comb. Chem. 2007, 9, 204.
[40] Lange, J. H. M.; Hofmeyer, L. J. F.; Hout, F. A. S.; Osnabrug, S. J. M.; Verveer, P. C.; Kruse, C. G.; Feenstra, R. W. Tetrahedron Lett. 2002, 43, 1101.
[41] Chen, S.; Huang, H.; Liu, X.; Shen, J.; Jiang, H.; Liu, H. J. Comb. Chem. 2008, 10, 358.
[42] Baqi, Y.; Müller, C. E. Org. Lett. 2007, 9, 1271.
[43] Pagnotta, M.; Pooley, C.; Gurland, B.; Choi, M. J. Phys. Org. Chem. 1993, 6, 407.

微波加速Ullmann反应的研究

Advances in Investigation of Ullmann Reaction Accelerated by Microwave Irradiation

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[2]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[3]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[4]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[5]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[6]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[7]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[8]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[9]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[10]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[11]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[12]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[13]	Ruixia Cao, Yuping Jia. Synthesis and Biological Activity of Novel Pyrrolo[2,3-d]pyrimidine Derivatives Containing Coumarin [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3304-3311.
[14]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.
[15]	Ran Zhou, Chunmei Yuan, Tao Zhang, Piao Mao, Yi Liu, Kaini Meng, Hui Xin, Wei Xue. Design, Synthesis and Bioactivity of Chalcone Derivative Containing Quinazolinone [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3196-3209.