Cu-Ag Bimetallic Nanoparticles Catalyzed Addition of Terminal Alkynes to Aldehydes

doi:10.6023/cjoc201512018

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (5): 1034-1043.DOI: 10.6023/cjoc201512018 Previous Articles Next Articles

ARTICLE

铜-银双金属纳米颗粒催化的醛-端炔加成反应研究

王超, 邓楠, 王玲玲, 许定健, 姚小泉

南京航空航天大学材料科学与技术学院南京 210016

收稿日期:2015-12-13 修回日期:2016-01-15 发布日期:2016-02-01
通讯作者: 姚小泉 E-mail:yaoxq@nuaa.edu.cn
基金资助:
国家自然科学基金(No.21172107)、江苏高校优势学科建设工程资助项目.

Cu-Ag Bimetallic Nanoparticles Catalyzed Addition of Terminal Alkynes to Aldehydes

Wang Chao, Deng Nan, Wang Lingling, Xu Dingjian, Yao Xiaoquan

Department of Applied Chemistry, Nanjing University of Aeronautics and Astronautics, Nanjing 210016

Received:2015-12-13 Revised:2016-01-15 Published:2016-02-01
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21172107), and the Priority Academic Program Development of Jiangsu Higher Education Institutions.

1. Cu-Ag Bimetallic Nanoparticles Catalyzed Addition of Terminal Alkynes to Aldehydes.PDF(6519KB)

Abstract

A copper-silver nanoparticles-catalyzed addition of terminal alkynes to aldehydes was developed for the synthesis of propargyl alcohols. With the promotion of bipyridine ligand, the bimetallic catalyst showed highly efficient to the reaction under neat condition, and good to excellent yields were achieved for various propargylic alcohols. In this catalytic reaction, a remarkable bimetallic synergistic effect was observed, in which Ag NPs worked as the co-catalyst and improved the catalytic activity of Cu NPs significantly. The nanoparticle catalyst could be recovered and reused effectively, and no obvious reduction on catalytic activity was observed after four recycles. Furthermore, a gram-scale reaction was also carried out successfully.

Key words: Cu-Ag bimetallic nanoparticles, co-catalysis, the addition of terminal alkynes to aldehydes, propargylic alcohols, synergistic effect

Cite this article

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.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Chng, L. L.; Erathodiyi, N.; Ying, J. Y. Acc. Chem. Res. 2013, 46, 1825.
[2] For recent reviews, see: (a) Gao, G.; Moore, D.; Xie, R. G.; Pu, L. Org. Lett. 2002, 4, 4143.
(b) Pu, L.; Yu, H. B. Chem. Rev. 2001, 101, 757.
(c) Frantz, D. E.; Fässler, R.; Tomooka, C. S.; Carreira, E. M. Acc. Chem. Res. 2000, 33, 373.
(d) Srihari, P.; Singh, V. K.; Bhunia, D. C.; Yadav, J. S. Tertrahedron Lett. 2008, 49, 7132.
(e) Zheng, B.; Li, Z. Y.; Liu, F. P.; Wu, Y. H.; Shen, J.-J.; Bian, Q. H.; Hou, S. C.; Wang. M. Molecules 2013, 18, 15422.
[3] He, Q. W.; Ma. S. M. Chin. J. Org. Chem. 2002, 22, 375.
[4] (a) Usanov, D. L.; Yamamoto, H. J. Am. Chem. Soc. 2011, 133, 1286.
(b) Li, X. S.; Lu, G.; Kwok, W. H. J. Am. Chem. Soc. 2002, 124, 12636.
(c) Xu, M. H.; Pu, L. Org. Lett. 2002, 4, 4555.
(d) Moore, D.; Pu, L. Org. Lett. 2002, 4, 1855.
(e) Li, Z. B.; Pu, L. Org. Lett. 2004, 6, 1065.
(f) Xu, Z. Q.; Hen, C.; Xu, J. K.; Miao, M. B.; Yan, W. J.; Wang, R. Org. Lett. 2004, 6, 1193.
(g) Liu, L.; Wang, R.; Chen, C.; Xu, Z. Q.; Zhou, Y. F.; Ni, M.; Kang, Y. F.; Cai, H. Q.; Gong, M. Z. J. Org. Chem. 2004, 4095.
[5] Some reviews and examples, see: (a) Trost, B. M.; Krische, M. J. J. Am. Chem. Soc. 1999, 121, 6131.
(b) Tzalis, D.; Knochel, P. Angew. Chem., In. Ed. 1999, 38, 1463.
(c) Friedrich, K. In the Chemistry of Triple-boned Functional Groups, Supplement C, Eds.: Patai, S.; Rappoport, Z., John Wiley & Sons: New York, 1983, Chapter 28.
(d) Brandsma, L.; Verkruijsse, H. D. Synthesis of Acetylenes, Allenes and Cumulenes, Elsevier, Amsterdam, 1981.
(e) Liu, J.; An, Y.; Wang, Y. H.; Jiang, H. Y.; Zhang, Y. X.; Chen, Z. L. Chem. Eur. J. 2008, 14, 9131.
[6] (a) Frantz, D. E.; Fässler, R.; Tomooka, C. S.; Carreira, E. M. J. Am. Chem. Soc. 2000, 8, 1806.
(b) Boyall, D.; Frantz, D. E.; Carreira, E. M. Org. Lett. 2002, 4, 2605.
(c) Anand, N. K.; Carreira, E. M. J. Am. Chem. Soc. 2001, 123, 9687.
(d) Li, M.; Zhu, X. Z.; Yuan, K.; Cao, B. X.; Hou, X. L. Tetrahedron: Asymmentry. 2004, 15, 219.
(e) Xu, Z. Q.; Chen, C.; Xu, J. K.; Miao, M. B.; Yan, W. J.; Wang, R. Org. Lett. 2004, 6, 1193.
[7] (a) Takita, R.; Fukuta, Y.; Tsuji, R.; Ohshima, T.; Shibasaki, M. Org. Lett. 2005, 7, 1363.
(b) Takita, R.; Fukuta, Y.; Tsuji, R.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 13760.
[8] Wei, C. M.; Li, C. J. Green Chem. 2002, 4, 39.
[9] Dhondi, P. K.; Chisholm, J. D. Org. Lett. 2006, 8, 67.
[10] Ito, J.; Asai, R.; Nishiyama, H. Org. Lett. 2010, 12, 3860.
[11] (a) Asano, Y.; Ito, H.; Hara, K.; Aswamur, M. Organometallics 2008, 27, 5984.
(b) Asano, Y.; Hara, K.; Ito, H.; Aswamur, M. Org. Lett., 2007, 9, 3901.
[12] (a) Yao, X. Q.; Li, C. J. Org. Lett. 2005, 7, 4395.
(b) Yu, M.; Skouta, R.; Zhou, L.; Jiang, H.; Yao, X.; Li, C. J. J. Org. Chem. 2009, 74, 3378.
[13] Yao, X. Q.; Li, C. J. Org. Lett. 2006, 8, 1953.
[14] For selected reviews, see: (a) Yasukawa, T.; Miyamura, H.; Kobayashi, S. Chem. Soc. Rev. 2014, 43, 1450.
(b) Shaikhutdinov, S.; Freund, H.-J. Acc. Chem. Res. 2013, 46, 1673.
(c) Hervés, P.; Pérez Lorenzo, M.; Liz-Marzán, L. M.; Dzubiella, J.; Lu, Y.; Ballauff, M. Chem. Soc. Rev. 2012, 41, 5577.
(d) Dhakshinamoorthy, A.; Garcia, H. Chem. Soc. Rev. 2012, 41, 5262.
(e) Shiju, N. R.; Guliants, V. V. Appl. Catal. A: Gen. 2009, 356, 1.
(f) Somorjai, G. A.; Park, J. Y. Angew. Chem., Int. Ed. 2008, 47, 9212.
(g) Gu, Y.; Li, G. Adv. Synth. Catal. 2009, 351, 817.
[15] Yu, M.; Han, C. Y.; Wang, Y.; Zhu, L.; Yao, X. Chin. J. Org. Chem. 2013, 33, 492 (in Chinese).
(喻敏, 韩成燕, 王勇, 朱荔, 姚小泉, 有机化学, 2013, 33, 492.)
[16] (a) Yu, M.; Lin, M.; Han, C.; Li, Z.; Li, C. J.; Yao, X. Q. Tetrahedron Lett. 2010, 51, 6722.
(b) Han, C.; Yu, M.; Sun, W.; Yao, X. Q. Synlett 2011, 2363.
(c) Yu, M.; Wang, Y.; Sun, W.; Yao, X. Q. Adv. Synth. Catal. 2012, 354, 71.
(d) Sun, W.; Wang, Y.; Wu, X.; Yao, X. Q. Green Chem. 2013, 15, 2356.
(e) Xu, S.; Zeng, S.; Wang, Y.; Yu, M.; Zhu, L.; Yao, X. Q. Chin. J. Org. Chem. 2015, 35, 827 (in Chinese).
(徐森, 曾书伟, 王勇, 喻敏, 朱荔, 姚小泉, 有机化学, 2015, 35, 827.) (f) Lv, W.; Tian, J.; Deng, N.; Wang, Y.; Zhu, X.; Yao, X. Tetrahedron Lett. 2015, 56, 1312.
(g) Wang, Y.; Wu. C. L.; Nie, S. J.; Xu, D. J.; Yao, X. Q. Tetrahedron. Lett. 2015, 56, 6827.
[17] For selected reviews, see: (a) Sun, Z.; He, J. M.; Qu, M. N.; Li, K. S. Chin. J. Org. Chem. 2015, 35, 1250 (in Chinese).
(孙哲, 何金梅, 屈孟男, 李侃社, 有机化学, 2015, 35, 1250.) (b) Allen, A. E.; MacMillan, D. W. C. Chem. Sci. 2012, 3, 633.
(c) Zhou, J. Chem. Asian J. 2010, 5, 422.
(d) Su, Y. J.; Jia, W.; Jiao, N. Synthesis. 2011, 1678.
(e) Zhang, Y. L.; Yan, W. W.; Sun, Z. M.; Li, X. C.; Gao, J. P. RSCAdv. 2014, 4, 38040.
(f) Mohammad, R. N.; Yasamin, B.; Maryam, A. RSC. Adv. 2014, 4, 35844.
[18] (a) Wei, C. M.; Li, C. J. J. Am. Chem. Soc. 2002, 124, 5638.
(b) Wei, C. M.; Mague, J. T.; Li, C. J. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5749.
[19] (a) Zhang, G.; Yi, H.; Zhang, G.; Deng, Y.; Bai, R.; Zhang, H.; Miller, J. T.; Kropf, A. J.; Bunel, E. E.; Lei, A. J. Am. Chem. Soc. 2014, 136, 924.
(b) Qi, X.; Li, Y.; Zhang, G.; Li, Y.; Lei, A.; Liu,; Lan, Y. Dalton Trans. 2015, 44, 11165.
(c) Yuan, J.; Wang, J.; Zhang, G.; Liu, C.; Qi, X.; Lan, Y.; Miller, J. T.; Kropf, J.; Bunel, E. E.; Lei, A. Chem. Commun. 2015, 51, 576.
(d) Tang, S.; Liu, Y.; Lei, A. Angew. Chem., Int. Ed. 2015, 54, 15850.
[20] Singh, M.; Sinha, I.; Singh, A. K.; Mandal, R. K. Colloid Surf., A 2005, 384, 668.
[21] Valodkar, M.; Modi, S.; Pal, A.; Thakore, S. Mater. Res. Bull. 2011, 46, 384.
[22] Tan, K. S.; Cheong, K. Y.; J. Nanopart. Res. 2013, 15, 1537.
[23] Li, Y. S.; Lu, Y. C.; Chou, K. S.; Liu, F. J. Mater. Res. Bull. 2010, 45, 1837.
[24] Grouchko, M.; Kamyshny, A.; Magdassi, S. J. Mater. Chem, 2009, 19, 3057.
[25] Butovsky, E.; Perelshtein, I.; Gedanken, A. J. Mater. Chem, 2012, 22, 15025.
[26] Kwok, H. N.; Penner, R. M. J. Electroanal. Chem. 2002, 522, 86.

铜-银双金属纳米颗粒催化的醛-端炔加成反应研究

Cu-Ag Bimetallic Nanoparticles Catalyzed Addition of Terminal Alkynes to Aldehydes

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 12

Recommended Articles

Metrics

Comments

[1]	Yingjie Liu, Gangqing Shi, Ge Chou, Xin Zhang, Dongxue Song, Ning Chen, Miao Yu, Ying Xu. Progress of α-Position Functionalization of Ethers under Photo/Electrocatalysis [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2664-2681.
[2]	Min Hua, Yangxing Sun, Xueqing Zhang, Hui Yao, Nianyu Huang. Convenient Cobalt-Catalyzed Stereoselective Synthesis of β-D-Thioglucosides [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2140-2154.
[3]	Li Cheng, Wenrong Wang, Yuqian Sun, Tuanjie Li, Chenxia Yu, Changsheng Yao. N-Heterocyclic Carbene (NHC)/Ag(I) Co-catalyzed Synthesis of 2-Oxo-2-arylethyl Aryl Formates [J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1607-1613.
[4]	Xu Wenzhi, Li Xue, Han Mengnan, Zhou Tingting, Yang Yutao, Li Wei. A Fluorescent Probe for Hydrazine Based on Synergistic Effect and Its Utilization in Cell Imaging [J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 181-185.
[5]	He Zhenxiu, Zhou Yongyun, Sun Weiqing, Fan Ruifeng, Shen Guol, Fan Baomin. Asymmetric Ring Opening Reaction of Oxabenzonorbornadienes with Phenols Promoted by Rhodium/Zinc Complexes [J]. Chin. J. Org. Chem., 2019, 39(3): 754-760.
[6]	Zhang Xiaoxiang, Lü Chang, Li Ping, Fu Bo, Yao Weiwei. Progress of the Research on the Lewis/Brønsted Acid-Catalyzed Nucleophilic Substitution of Propargyl Alcohols [J]. Chin. J. Org. Chem., 2016, 36(6): 1287-1298.
[7]	Yang Zonglian, Liao Peiqiu, Li Xingqi, Bi Xihe. Pentynenones Formation through Copper Catalyzed Coupling- Isomerization Reaction between Alkynyl Bromides and Propargylic Alcohols [J]. Chin. J. Org. Chem., 2015, 35(3): 610-617.
[8]	Xu Wenshuai, Zhao Shoujing, Luo Xiaopei, Song Jinna, Liu Jianquan, Bi Xihe, Liao Peiqiu. Silver-Catalyzed Cross-Coupling Reaction of Propargylic Alcohols and Arylisocyanides: An Atom-Economic Synthesis of N-Aryl-2,3-allenamides [J]. Chin. J. Org. Chem., 2015, 35(10): 2095-2101.
[9]	ZHANG Li-Li,LIU An-Hua*,ZENG Xing-Rong. Synthesis of Caged Bicyclic Phosphorous-Functionalized Silsesquioxane [J]. Chin. J. Org. Chem., 2007, 27(03): 424-427.
[10]	Liao Dezhong;He Jieyu. A study on catalytic performance of a new solid acid SO^2^-~4-MoO3- TiO2 in preparation of n-butyl propanoate [J]. Chin. J. Org. Chem., 2001, 21(12): 1153-1156.
[11]	Liu Zhongli. Microenvironmental effects and synergistic effects of bio- antioxidants [J]. Chin. J. Org. Chem., 2001, 21(11): 884-889.
[12]	YANG BINGHUI;JIANG JIQING. Recent development in the synthesis of C-glycosides [J]. Chin. J. Org. Chem., 1998, 18(4): 303-310.