Dimerization Coupling Reaction of Terminal Alkyne Promoted by CuI/DEAD

doi:10.6023/cjoc201406016

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (1): 207-211.DOI: 10.6023/cjoc201406016 Previous Articles Next Articles

Notes

CuI/DEAD促进的端炔的二聚偶联反应

杨振平, 王兵南, 许孝良, 王红, 李小年

浙江工业大学化工学院杭州 310014

收稿日期:2014-06-13 修回日期:2014-09-29 发布日期:2014-10-13
通讯作者: 许孝良, 王红 E-mail:xuxiaoliang@zjut.edu.cn;chem_hong@163.com
基金资助:
浙江省自然科学基金(No. LY12B02017)资助项目.

Dimerization Coupling Reaction of Terminal Alkyne Promoted by CuI/DEAD

Yang Zhenping, Wang Bingnan, Xu Xiaoliang, Wang Hong, Li Xiaonian

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Received:2014-06-13 Revised:2014-09-29 Published:2014-10-13
Supported by:
Project supported by the Zhejiang Provincial Natural Science Foundation of China (No. LY12B02017).

1. Dimerization Coupling Reaction of Terminal Alkyne Promoted by CuI/DEAD.PDF(2656KB)

Abstract

The dimerization coupling reaction of terminal alkynes is an important method for the synthesis of conjugated carbon-carbon triple bond compounds. Catalyzed by CuI and assisted by diethyl azodicarboxylate, a variety of aromatic and aliphatic alkynes could be dimerized to give the Glaser coupling products using a catalytic amount of N-methylimidazole as a base. The effect of copper catalysts and solvents on this reaction was surveyed. It has the advantage of high yields, simple operation, and mild reaction condition.

Key words: CuI, diethyl azodicarboxylate, terminal alkyne, Glaser reaction

Cite this article

Yang Zhenping, Wang Bingnan, Xu Xiaoliang, Wang Hong, Li Xiaonian. Dimerization Coupling Reaction of Terminal Alkyne Promoted by CuI/DEAD[J]. Chin. J. Org. Chem., 2015, 35(1): 207-211.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Nair, V.; Biju, A. T.; Mathew, S. C.; Babu, B. P. Chem. Asian J. 2008, 3, 810.
[2] Curtius, T.; Heidenreich, K. Ber. Dtsch. Chem. Ges. 1894, 27, 773.
[3] (a) Diels, O. Justus Liebigs Ann. Chem. 1922, 429, 1. (b) Diels, O.; Blom, J. H.; Koll, W. Justus Liebigs Ann. Chem. 1925, 443, 242. (c) Kharasch, M. S.; White, P. C.; Mayo, F. R. J. Org. Chem. 1938, 3, 33. (d) Huisgen, R. In The Adventure Playground of Mechanisms and Novel Reactions: Profiles, Pathways and Dreams, Ed.: Seeman, J. I., American Chemical Society, Washington DC, 1994, p. 62. (e) Brunn, E.; Huisgen, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 513. (f) Alder, K.; Pascher, F.; Schmitz, A. Ber. Dtsch. Chem. Ges. 1943, 76, 27.
[4] Swamy, K. C. K.; Kumar, N. N. B.; Balaraman, E.; Kumar, K. V. P. P. Chem. Rev. 2009, 109, 2551.
[5] (a) Mitsunobu, O.; Yamada, M.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1967, 40, 935. (b) Mitsunobu, O.; Yamada, M. Bull. Chem. Soc. Jpn. 1967, 40, 2380. (c) Mitsunobu, O.; Eguchi, M. Bull. Chem. Soc. Jpn. 1971, 44, 3427.
[6] (a) Liu, C.; Zhu, Q.; Huang, K. W.; Lu, Y. X. Org. Lett. 2011, 13, 2638. (b) Fu, J. Y.; Yang, Q. C.; Wang, Q. L.; Ming, J. N.; Wang, F. Y.; Xu, X. Y.; Wang, L. X. J. Org. Chem. 2011, 76, 4661. (c) List, B. J. Am. Chem. Soc. 2002, 124, 5656.
[7] (a) Galzerano, P.; Pesciaioli, F.; Mazzanti, A.; Bartoli, G.; Melchiorre, P. Angew. Chem., Int. Ed. 2009, 48, 7892. (b) Bertelsen, S.; Marigo, M.; Brandes, S.; Diner, P.; Jørgensen, K. A. J. Am. Chem. Soc. 2006, 128, 12973.
[8] (a) Chang, L.; Kuang, Y. L.; Qin, B.; Zhou, X.; Liu, X. H.; Lin, L. L.; Feng, X. M. Org. Lett. 2010, 12, 2214. (b) Matsubara, R.; Kobayashi, S. Angew. Chem., Int. Ed. 2006, 45, 7933. (c) Poulsen, T. B.; Alemparte, C.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 11614.
[9] (a) Yu, W. Y.; Sit, W. N.; Lai, K. M.; Zhou, Z. Y.; Chan, A. S. C. J. Am. Chem. Soc. 2008, 130, 3304. (b) Brandes, S.; Bella, M.; Kjrsgaard, A.; Jørgensen, K. A. Angew. Chem., Int. Ed. 2006, 45, 1147. (c) Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682.
[10] (a) Hong, D.; Zhu, Y. X.; Lin, X. F.; Wang, Y. G. Tetrahedron 2011, 67, 650. (b) Su, Y. H.; Jiang, Z.; Hong, D.; Lu, P.; Wang, Y. G.; Lin, X. F. Tetrahedron Lett. 2010, 66, 2427. (c) Cui, S. L.; Wang, J.; Wang, Y. G. Org. Lett. 2008, 10, 13. (d) Nair, V.; Mathew, S. C.; Biju, A. T.; Suresh, E. Angew. Chem., Int. Ed. 2007, 46, 2070. (e) Brunn, B. E.; Huisgen, R. Angew. Chem., Int. Ed. 1969, 8, 513.
[11] (a) Monbaliu, J. C.; Tinant, B.; Peeters, D.; Marchand-Brynaert, J. Tetrahedron Lett. 2010, 51, 1052. (b) Avalos, M.; Babiano, R.; Cintas, P.; Clemente, F. R.; Jimenez, J. L.; Palacios, J. C.; Sanchez, J. B. J. Org. Chem. 1999, 64, 6297. (c) Cohen, B. S. G.; Zand, R.; Steel, C. J. Am. Chem. Soc. 1961, 83, 2895.
[12] (a) Wei, D. H.; Zhu, Y. Y.; Zhang, C.; Sun, D. Z.; Zhang, W. J.; Tang, M. S. J. Mol. Catal. A: Chem. 2011, 334, 108. (b) Huang, X. L.; Chen, X. Y.; Ye, S. J. Org. Chem. 2009, 74, 7585. (c) Berlin, J. M.; Fu, G. C. Angew. Chem., Int. Ed. 2008, 47, 7048.
[13] (a) Cao, H. T.; Gree, R. Tetrahedron Lett. 2009, 50, 1493. (b) Hayashi, M.; Matsuura, Y.; Watanabe, Y. Tetrahedron Lett. 2004, 45, 1409.
[14] Muniz, K.; Iglesias, A. Angew. Chem., Int. Ed. 2007, 46, 6305.
[15] Glaser, C. Ber. Dtsch. Chem. Ges. 1869, 2, 422.
[16] Eglinton, G.; Galbraith, A. R. Chem. Ind. (London) 1956, 737.
[17] Hay, A. S. J. Org. Chem. 1962, 27, 3320.
[18] Rossi, R.; Carpita, A.; Bigelli, C. Tetrahedron Lett. 1985, 26, 523.
[19] Liu, Q.; Burton, D. J. Tetrahedron Lett. 1997, 38, 4371.
[20] Bharathi, P.; Periasamy, M. Organometallics 2000, 19, 5511.
[21] Kraffe, M. E.; hirosawa, C.; Dalal, N.; Ramsey, C.; Stiegman, A. Tetrahedron Lett. 2001, 42, 7733.
[22] Kabalka, G. W.; Wang, L.; Pagni, R. M. Synlett 2001, 108.
[23] Yadav, J. S.; Reddy, B. V. S.; Bhaskar Reddy, K.; Gayathri, U. K.; Prasad, A. R. Tetrahedron Lett. 2003, 44, 6493.
[24] Li, P. H.; Yan, J. C.; Wang, M.; Wang, L. Chin. J. Chem. 2004, 22, 219.
[25] Li, J. H.; Liang, Y.; Zhang, X. D. Tetrahedron 2005, 61, 1903.
[26] (a) Xu, X. L.; Du, P.; Cheng, D. P.; Wang, H.; Li, X. N. Chem. Commun. 2012, 48, 1811. (b) Xu, X. L.; Li, X. N. Org. Lett. 2009, 11, 1027. (c) Xu, X. L.; Li, X. N.; Ma, L.; Ye, N.; Weng. B. J. J. Am. Chem. Soc. 2008, 130, 14048. (d) Xu, X. L.; Cheng, G. H.; Li, X. N. Chin. J. Org. Chem. 2012, 32, 1024 (in Chinese). (许孝良, 程国华, 李小年, 有机化学, 2012, 32, 1024.)
[27] Ouyang, K. B.; Xi, Z. F. Acta Chim. Sinica 2013, 71, 13 (in Chinese). (欧阳昆冰, 席振峰, 化学学报, 2013, 71, 13.)
[28] Merkul, E.; Urselmann, D.; Müller, T. J. J. Eur. J. Org. Chem. 2011, 238.
[29] Yu, S. S.; You, X.; Liu, Y. H. Chem. Eur. J. 2012, 18, 13936.
[30] Jia, X. S.; Yin, K.; Li, C. J.; Li, J.; Bian, H. S. Green Chem. 2011, 8, 2175.
[31] Zhu, Y. G.; Shi, Y. Org. Biomol. Chem. 2013, 11, 7451.
[32] Singh, F. V.; Amaral, M. F. Z. L.; Stefani, H. A. Tetrahedron Lett. 2009, 50, 2636.
[33] Zheng, Q.; Hua, R.; Wan, Y. Appl. Organomet. Chem. 2010, 24, 314.
[34] Wang, A.-Z.; Jiang, H.-F. Chin. J. Org. Chem. 2007, 27, 619 (in Chinese). (王阿忠, 江焕峰, 有机化学, 2007, 27, 619.)
[35] Liu, D.-X., Li, F.-L.; Li, H.-X.; Gao, J.; Lang, J.-P. Tetrahedron 2014, 70, 2416.
[36] Susanto, W.; Chu, C.-Y.; Ang, W. J.; Chou, T.-C.; Lo, L.-C.; Lam, Y. J. Org. Chem. 2012, 77, 2729.
[37] Kurita, T.; Abe, M.; Maegawa, T.; Monguchi, Y.; Sajiki, H. Synlett 2007, 2521.
[38] Perez, J. M.; Cano, R.; Yue, M.; Ramon, D. J. Synthesis 2013, 45, 1373.

CuI/DEAD促进的端炔的二聚偶联反应

Dimerization Coupling Reaction of Terminal Alkyne Promoted by CuI/DEAD

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Fei Chen, Sheng Tao, Ning Liu, Bin Dai. CNN-Type Binuclear Cu(I) Complexes Catalyzed Direct Carboxylation via the Fixation of CO₂ at Room Temperature [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2471-2480.
[2]	Liwen Ma, Xiaoye Wei, Zilin Zhao, Ang Zhao, Xiangwen Deng, Bingnan Huo, Gang Ma, Chunfang Zhang. Theoretical Study on the Catalytic Mechanism of Copper with Various Valence for the Terminal Alkyne Coupling Reaction [J]. Chinese Journal of Organic Chemistry, 2022, 42(6): 1811-1819.
[3]	Yinyin Wang, Xiaowan Lin, Piao Zhang, Meihua Shen, Huadong Xu, Defeng Xu. Design and Synthesis of Pyridine and 1,3,5-Triazine PNP Pincer Ligands and Their Application in Cobalt Catalyzed Semihydrogenation of Terminal Alkynes [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3312-3320.
[4]	Jingru Liang, Bingying Wang, Chengyin Huang, Xiaojun Ye, Yanmei Wen. Synthesis of Symmetrical (E,E)-1,4-Diaryl-1,3-butadienes by One-Pot Method [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2116-2120.
[5]	Peng Zhou, Shangwei Feng, Huihua Qiu, Jiantao Zhang. Sodiump-Toluenesulfinate/KI-Mediated Aerobic Oxidative Iodination of Terminal Alkynes for Synthesis of 1-Iodoalkynes and 1,3-Diynes [J]. Chinese Journal of Organic Chemistry, 2021, 41(1): 394-399.
[6]	Yao Ming, Zhang Jingjing, Yang Sen, Xiong Hangxing. γ-Aluminum Oxide-Mediated Iodination of Terminal Alkynes [J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2153-2158.
[7]	Hu Zhifang, Peng Lifen, Qiu Renhua, Orita Akihiro. Recent Progress of Protecting Groups for Terminal Alkynes [J]. Chinese Journal of Organic Chemistry, 2020, 40(10): 3112-3119.
[8]	Xie Zongbo, Li Hongxia, Liu Liansheng, Lan Jin, Hu Zhiyu, Le Zhanggao. Synthesis of Quinazolinone Derivatives Catalyzed by Alkaline Protease [J]. Chin. J. Org. Chem., 2019, 39(9): 2632-2638.
[9]	Liu Ruiting, Li Zhen, Wang Shengke, Zhou Xigeng. Pd(OAc)₂/CuI-Catalyzed Tandem Reaction for Synthesis of Polysubstituted 3-Chalcogenylindoles [J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3215-3222.
[10]	Wang, Yaqi, Yin, Qiang, Guo, Dun, Han, Limin, Sun, Qi, Hong, Hailong, Suo, Quanling, Suo. Quanling. Carbonyl Cobalt-Catalyzed Cyclotrimerization of Terminal Alkynes in Supercritical Carbon Dioxide [J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2898-2905.
[11]	Ma Nan, Zeng Xianghua. Cu₂O-Catalyzed Green Oxidative Terminal Alkynes Homocoupling without Bases [J]. Chin. J. Org. Chem., 2018, 38(6): 1556-1561.
[12]	Qi Haitang, Song Guanglin, Quan Zhengjun, Wang Xicun. CuSO₄·5H₂O/NaAsc-Catalyzed Sonogashira Coupling Reaction of Aryl Iodides and Terminal Alkynes [J]. Chin. J. Org. Chem., 2017, 37(7): 1855-1859.
[13]	Zhang Qingyang, Wang Xiaojian, Xiao Qiong, Yin Dali. One Pot Solvent-Free Synthesis of Benzodiazepinones Catalyzed by CuI [J]. Chin. J. Org. Chem., 2017, 37(4): 954-958.
[14]	Guan Zhipeng, Shi Yao, Shi Wei, Chen Hao. Synthesis of Terminal Alkynes/Diynes through Deprotection of Acetone Protected Alkynes under Mild Conditions [J]. Chin. J. Org. Chem., 2017, 37(2): 418-422.
[15]	Wang Chao, Deng Nan, Wang Lingling, Xu Dingjian, Yao Xiaoquan. Cu-Ag Bimetallic Nanoparticles Catalyzed Addition of Terminal Alkynes to Aldehydes [J]. Chin. J. Org. Chem., 2016, 36(5): 1034-1043.