Progress in Transition-Metal-Catalyzed Oxidative Cross-Coupling of Terminal Alkynes

doi:10.6023/cjoc201307024

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (1): 81-91.DOI: 10.6023/cjoc201307024 Previous Articles Next Articles

Reviews

过渡金属催化端炔的氧化交叉偶联反应研究进展

张聪霞, 李娜娜, 李兴, 常宏宏, 刘强, 魏文珑

太原理工大学化学化工学院生物与制药工程系太原 030024

收稿日期:2013-07-20 修回日期:2013-09-03 发布日期:2013-09-17
通讯作者: 魏文珑 E-mail:weiwenlong@tyut.edu.cn
基金资助:
山西省自然科学基金（Nos. 2012021007-2，2011011010-2）及山西省高等教育机构科技创新（No. 20120006）资助项目.

Progress in Transition-Metal-Catalyzed Oxidative Cross-Coupling of Terminal Alkynes

Zhang Congxia, Li Nana, Li Xing, Chang Honghong, Liu Qiang, Wei Wenlong

College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024

Received:2013-07-20 Revised:2013-09-03 Published:2013-09-17
Supported by:
Project supported by the Natural Science Foundation of Shanxi Province (Nos. 2012021007-2, 2011011010-2), and the Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi Province (No. 20120006).

Alkynyl compounds are one kind of important functional compounds in organic synthesis. Various new alkynyl compounds can be obtained via oxidative cross-coupling reactions of terminal alkynes. Recent oxidative cross-coupling reactions involving terminal alkynes are reviewed. The advances of cross-coupling reactions catalyzed by Pd, Cu, Fe and so on are particularly described.

Key words: transition metal, C—H bond, terminal alkyne, oxidative cross-coupling, progress

Cite this article

Zhang Congxia, Li Nana, Li Xing, Chang Honghong, Liu Qiang, Wei Wenlong. Progress in Transition-Metal-Catalyzed Oxidative Cross-Coupling of Terminal Alkynes[J]. Chin. J. Org. Chem., 2014, 34(1): 81-91.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Ullmann, F. Ber. Dtsch. Chem. Ges. 1903, 36, 2382.

[2] Zhang, B. B.; Zhan, D.; Zhang, X. P.; Xiang, Q. J.; Zeng, Q. L. Acta Chim. Sinica 2012, 70, 1655 (in Chinese).

(张斌彬, 詹丹, 张小平, 向沁洁, 曾庆乐, 化学学报, 2012, 70, 1655.)

[3] Darses, S.; Genet, J. P. Chem. Rev. 2008, 108, 288.

[4] Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.

[5] Alonso, F.; Beletskaya, I. P.; Yus, M. Tetrahedron 2005, 61, 11771.

[6] (a) Li, X.; Yan, X. Y.; Chang, H. H.; Wang, L. C.; Zhang, Y.; Chen, W. W.; Li, Y. W.; Wei, W. L. Org. Biomol. Chem. 2012, 10, 495.

(b) Li, X.; Wang, L. C.; Chang, H. H.; Zhang, C. X.; Wei, W. L. Appl. Catal. A: Gen. 2013, 462～463, 15.

[7] Wen, Y. M.; Jiang, H. F. Acta Chim. Sinica 2012, 70, 1716 (in Chinese).

(温燕梅, 江焕峰, 化学学报, 2012, 70, 1716.)

[8] Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.

[9] Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879.

[10] Jia, C. G.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633.

[11] Li, H.; Li, B. J.; Shi, Z. J. Catal. Sci. Technol. 2011, 1, 191.

[12] (a) Pan, F.; Shi, Z. J. Acta Chim. Sinica 2012, 70, 1679 (in Chinese).

(潘菲, 施章杰, 化学学报, 2012, 70, 1679.;

b) Zhang, D.; Qin, Y. Acta Chim. Sinica 2013, 71, 147 (in Chinese).

(张丹, 秦勇, 化学学报, 2013, 71, 147.)

[13] Li, C. J. Acc. Chem. Res. 2009, 42, 335.

[14] Li, Z. P.; Li, C. J. J. Am. Chem. Soc. 2005, 127, 3672.

[15] Cai, G. X.; Fu, Y.; Li, Y. Z.; Wan, X. B.; Shi, Z. J. J. Am. Chem. Soc. 2007, 129, 7666.

[16] Huber, S. M.; Ertem, M. Z.; Aquilante, F.; Gagliardi, L.; Tolman, W. B.; Cramer, C. J. Chem. Eur. J. 2009, 15, 4886.

[17] Sonogashira, K. J. Organomet. Chem. 2002, 653, 46.

[18] Glaser, C. Ber. Dtsch. Chem. Ges. 1869, 2, 422.

[19] Glaser, C. Ann. Chem. Pharm. 1870, 154, 137.

[20] Kim, S. H.; Yoon, J.; Chang, S. Org. Lett. 2011, 13, 1474.

[21] Liang, B.; Dai, M. J.; Chen, J. H.; Yang, Z. J. Org. Chem. 2005, 70, 391.

[22] Li, J. H.; Liang, Y.; Xie, Y. X. J. Org. Chem. 2005, 70, 4393.

[23] Hadi, V.; Yoo, K. S.; Jeong, M.; Jung, K. W. Tetrahedron Lett. 2009, 50, 2370.

[24] Chen, M.; Zheng, X. L.; Li, W. Q.; He, J.; Lei, A. W. J. Am. Chem. Soc. 2010, 132, 4101.

[25] Luh, T. Y.; Leung, M. K.; Wong, K. T. Chem. Rev. 2000, 100, 3187.

[26] Facoetti, D.; Abbiati, G.; d'Avolio, L.; Ackermann, L.; Rossi, E. Synlett 2009, 2273.

[27] Yue, D. W.; Larock, R. C. Org. Lett. 2004, 6, 1037.

[28] Zhang, H. M.; Larock, R. C. J. Org. Chem. 2002, 67, 7048.

[29] Gu, Y. H.; Wang, X. M. Tetrahedron Lett. 2009, 50, 763.

[30] Besselièvre, F.; Piguel, S. Angew. Chem., Int. Ed. 2009, 48, 9553.

[31] Brand, J. P.; Charpentier, J.; Waser, J. Angew. Chem., Int. Ed. 2009, 48, 9346.

[32] Yang, L.; Zhao, L.; Li, C. J. Chem. Commun. 2010, 46, 4184.

[33] Zou, G.; Zhu, J. R.; Tang, J. Tetrahedron Lett. 2003, 44, 8709.

[34] Yang, F.; Wu, Y. J. Eur. J. Org. Chem. 2007, 3476.

[35] Ye, Z. S.; Liu, M. C.; Lin, B. D.; Wu, H. Y.; Ding, J. C.; Cheng, J. Tetrahedron Lett. 2009, 50, 530.

[36] Wu, C. R.; Li, P.; Fang, Y. S.; Zhao, J. J.; Xue, W. C.; Li, Y.; Larock, R. C.; Shi, F. Tetrahedron Lett. 2011, 52, 3797.

[37] Jie, X. M.; Shang, Y. P.; Hu, P.; Su, W. P. Angew. Chem., Int. Ed. 2013, 52, 3535.

[38] Zhou, L.; Ye, F.; Ma, J. C.; Zhang, Y.; Wang, J. B. Angew. Chem., Int. Ed. 2011, 50, 3510.

[39] Hamada, T.; Ye, X.; Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 833.

[40] Wang, L.; Huang, H.; Priebbenow, D. L.; Pan, F. F.; Bolm, C. Angew. Chem., Int. Ed. 2013, 52, 3478.

[41] Wei, Y.; Zhao, H. Q.; Kan, J.; Su, W. P.; Hong, M. C. J. Am. Chem. Soc. 2010, 132, 2522.

[42] Matsuyama, N.; Kitahara, M.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett. 2010, 12, 2358.

[43] Iorga, B.; Eymery, F.; Carmichael, D.; Savignac, P. Eur. J. Org. Chem. 2000, 3103.

[44] Lera, M.; Hayes, C. J. Org. Lett. 2000, 2, 3873.

[45] Gao, Y. X.; Wang, G.; Chen, L.; Xu, P. X.; Zhao, Y. F.; Zhou,Y. B.; Han, L. B. J. Am. Chem. Soc. 2009, 131, 7956.

[46] Kitahara, M.; Hirano, K.; Tsurugi, H.; Satoh, T.; Miura, M. Chem. Eur. J. 2010, 16, 1772.

[47] Chu, L. L.; Qing, F. L. J. Am. Chem. Soc. 2010, 132, 7262.

[48] Li, Z. P.; Li, C. J. J. Am. Chem. Soc. 2004, 126, 11810.

[49] Zhao, L.; Li, C. J. Angew. Chem., Int. Ed. 2008, 47, 7075.

[50] Bi, H. P.; Zhao, L.; Liang, Y. M.; Li, C. J. Angew. Chem., Int. Ed. 2009, 48, 792.

[51] Niu, M. Y.; Yin, Z. M.; Fu, H.; Jiang, Y. Y.; Zhao, Y. F. J. Org. Chem. 2008, 73, 3961.

[52] Pan, C. D.; Luo, F.; Wang, W. H.; Ye, Z. S.; Cheng, J. Tetrahedron Lett. 2009, 50, 5044.

[53] Jiang, X. L.; Chu, L. L.; Qing, F. L. Org. Lett. 2012, 14, 2870.

[54] Xu, X. L.; Li, X. N. Org. Lett. 2009, 11, 1027.

[55] Xu, Z. W.; Yu, X. Q.; Feng, X. J.; Bao, M. J. Org. Chem. 2011, 76, 6901.

[56] Stavropoulos, P.; Çelenligil-Çetin, R.; Tapper, A. E. Acc. Chem. Res. 2001, 34, 745.

[57] Walling, C. Acc. Chem. Res. 1998, 31, 155.

[58] Volla, C. M. R.; Vogel, P. Org. Lett. 2009, 11, 1701.

[59] (a) Horner, L.; Junkermann, H. Ann. Chem. Justus Liebig 1955, 591, 53.

(b) Horner, L.; Kirmse, W. Ann. Chem. Justus Liebig 1955, 597, 48.

[60] Meng, X.; Li, C. B.; Han, B. C.; Wang, T. S.; Chen, B. H. Tetrahedron 2010, 66, 4029.

[61] You, X. L.; Xu, L.; Hu, T. Lett. Org. Chem. 2012, 9, 300.

[62] Yin, W. Y.; He, C.; Chen, M.; Zhang, H.; Lei, A. W. Org. Lett. 2009, 11, 709.

[63] He, C.; Hao, J.; Xu, H.; Mo, Y. P.; Liu, H. Y.; Han, J. J.; Lei, A. W. Chem. Commun. 2012, 48, 11073.

[64] He, C.; Guo, S.; Ke, J.; Hao, J.; Xu, H.; Chen, H. Y.; Lei, A. W. J. Am. Chem. Soc. 2012, 134, 5766.

[65] de Haro, T.; Nevado, C. J. Am. Chem. Soc. 2010, 132, 1512.

过渡金属催化端炔的氧化交叉偶联反应研究进展

Progress in Transition-Metal-Catalyzed Oxidative Cross-Coupling of Terminal Alkynes

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Jie Liu, Feng Han, Shuangyan Li, Tianyu Chen, Jianhui Chen, Qing Xu. Transition Metal-Free Selective Aerobic Olefination of Methyl N-Heteroarenes with Alcohols [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 573-583.
[2]	Xiaoying Jia, Jiaxia Pu, Lirong Han, Qinghan Li. Research Progress in the Synthesis of Benzo[d]pentamembered Heterocyclic Thioethers Containing Two Heteroatoms [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 18-40.
[3]	Hongqiong Zhao, Miao Yu, Dongxue Song, Qi Jia, Yingjie Liu, Yubin Ji, Ying Xu. Progress on Decarboxylation and Hydroxylation of Carboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 70-84.
[4]	Xiaoyang Gao, Ruirui Zhai, Xun Chen, Shuojin Wang. Recent Progress in C—H Bond Activation Reaction with Vinylene Carbonate [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3119-3134.
[5]	Wenfang Wang. Recent Progress in Transition-Metal-Catalyzed Asymmetric C—H Borylation [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3146-3166.
[6]	Jiaxia Pu, Xiaoying Jia, Lirong Han, Qinghan Li. Research Progress of Visible Light Promoted C—N Bond Fracture to Construct C—C Bond [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2591-2613.
[7]	Sifan Dong, Haolong Li, Yuan Qin, Shiming Fan, Shouxin Liu. Research Progress of Amino Acids as Transient Directing Groups in C—H Bond Activation Reactions [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2351-2367.
[8]	Zhongrong Xu, Jieping Wan, Yunyun Liu. Transition Metal-Free C—H Thiocyanation and Selenocyanation Based on Thermochemical, Photocatalytic and Electrochemical Process [J]. Chinese Journal of Organic Chemistry, 2023, 43(7): 2425-2446.
[9]	Yangyang Chu, Zhaobin Han, Kuiling Ding. Progresses in the Application of Kinetic Resolution in Transition Metal Catalyzed Asymmetric (Transfer) Hydrogenation [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1934-1951.
[10]	Guangli Xu, Jing Xu, Haidong Xu, Xiang Cui, Xingzhong Shu. Research Progress of Transition Metal Catalyzed Synthesis of 1,3- Conjugated Diene Compounds from Alkenes and Alkynes [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1899-1933.
[11]	Xiaojing Hu, Feixiang Guo, Runqing Zhu, Bingqi Zhou, Tao Zhang, Lizhen Fang. Synthesis of p-Alkoxy Phenol and Its Application after Dearomatization [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2239-2244.
[12]	Jiao Qin, Jie Chen, Yan Su. Synthesis of 2,2,6,6-Tetramethylpiperidin-1-yl-2-(2-cyanophenyl)-acetate by Transition Metal-Free Radical Cleavage Reaction from α-Bromoindanone [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2171-2177.
[13]	Ke Jing, Panke Zhang, Senmiao Xu. Application of 1,4-Azaborines in Organic and Transition Metal Catalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1742-1750.
[14]	Kanghui Duan, Junlong Tang, Wanqing Wu. Recent Advances in the Synthesis of Fused Heterocyclic Compounds and Their Antitumor Activities [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 826-854.
[15]	Hairui Jia, Zaozao Qiu. Recent Advances in Transition Metal-Catalyzed B—H Bond Activation for Synthesis of o-Carborane Derivatives with B—Heteroatom Bond [J]. Chinese Journal of Organic Chemistry, 2023, 43(3): 1045-1068.