Design and Synthesis of Novel 1,10-Phenanthroline Derivatives

doi:10.6023/cjoc201501005

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (8): 1792-1796.DOI: 10.6023/cjoc201501005 Previous Articles Next Articles

NOTE

新型1,10-菲咯啉衍生物的设计与合成

金海明^a, 邹亮^a, 陈南雨^a, 孙圆圆^a, 罗书平^a, Junge Henrik^b, Beller Matthias^b

a 浙江工业大学化学工程学院绿色化学合成技术国家重点实验室培育基地杭州 310014;
b 罗斯托克大学莱布尼茨催化研究所罗斯托克 18059 德国

收稿日期:2015-01-05 修回日期:2015-03-20 发布日期:2015-04-10
通讯作者: 罗书平 E-mail:luoshuping@zjut.edu.cn
基金资助:
国家自然科学基金(Nos. 21361130021, 21376222)资助项目.

Design and Synthesis of Novel 1,10-Phenanthroline Derivatives

Jin Haiming^a, Zou Liang^a, Chen Nanyu^a, Sun Yuanyuan^a, Luo Shuping^a, Henrik Junge^b, Matthias Beller^b

a State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014;
b Leibniz Institute for Catalysis at the University of Rostock LIKAT, Rostock 18059, Germany

Received:2015-01-05 Revised:2015-03-20 Published:2015-04-10
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21361130021, 21376222).

1. Design and Synthesis of Novel 1,10-Phenanthroline Derivatives.PDF(749KB)

Abstract

To access functionalized nitrogen ligands, a series of novel 1,10-phenanthroline derivatives 1a~1d were designed and synthesized. Starting from 1-bromoaryl-3-chloroacetone (2) and o-phenylenediamine (3), 4,7-dibromoaryl-1,10-phenanthroline (4) were obtained in up to 64% yield by using a straightforward one-pot method catalyzed by mixed acids. Next, halogen lithium exchange reactions were performed to give 4. Finally, quenching of the reaction mixture with CO₂gave the desired 2,9-dialkyl-4,7-bis(carboxy-aryl)-1,10-phenanthroline derivatives 1 in up to 59% yield. This work provides a simple and convenient route to synthesize new 2,9-alkylated carboxylic acid-functionalized phenanthrolines.

Key words: 1,10-phenanthroline derivatives, o-phenylenediamine, one pot, carboxylic acid

Cite this article

Jin Haiming, Zou Liang, Chen Nanyu, Sun Yuanyuan, Luo Shuping, Henrik Junge, Matthias Beller. Design and Synthesis of Novel 1,10-Phenanthroline Derivatives[J]. Chin. J. Org. Chem., 2015, 35(8): 1792-1796.

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[1] (a) Dotsenko, I. A.; Curtis, M.; Samoshina, N. M.; Samoshin, V. V. Tetrahedron 2011, 67, 7470. (b) Nam, H.; Jeong, M.; Sohn, O.-J.; Rhee, J. I.; Oh, J.; Kim, Y.; Lee, S. Inorg. Chem. Commun. 2007, 10, 195.
[2] (a) Wang, T.; Chen, F.; Qin, J.; He, Y. M.; Fan, Q. H. Angew. Chem., Int. Ed. 2013, 52, 7172. (b) Jeong, M.; Nam, H.; Sohn, O.-J.; Rhee, J. I.; Kim, H. J.; Cho, C.-W.; Lee, S. Inorg. Chem. Commun. 2008, 11, 97. (c) Van den Bosch, B.; Chen, H. C.; van der Vlugt, J. I.; Brouwer, A. M.; Reek, J. N. ChemSusChem 2013, 6, 790. (d) Colombo, A.; Dragonetti, C.; Magni, M.; Roberto, D.; Demartin, F.; Caramori, S.; Bignozzi, C. A. ACS Appl. Mat. Interfaces 2014, 6, 13945. (e) Wei, J.; Zhang, T.-T.; Jia, J.; Wu, H.-S. Struct. Chem. 2015, 26, 421. (f) Luo, S.-P.; Mejía, E.; Friedrich, A.; Pazidis, A.; Junge, H.; Surkus, A.-E.; Jackstell, R.; Denurra, S.; Gladiali, S.; Lochbrunner, S.; Beller, M. Angew. Chem., Int. Ed. 2013, 52, 419.
[3] (a) Saggadi, H.; Luart, D.; Thiebault, N.; Polaert, I.; Estel, L.; Len, C. RSC Adv. 2014, 4, 21456. (b) Výprachtický, D.; Kaňková, D.; Pokorná, V.; Kmínek, I.; Dzhabarov, V.; Cimrová, V. Aust. J. Chem. 2014, 67, 915.
[4] Cai, L.-L.; Zhao, H.-Y.; Zhang, W.-L.; Dai, L. WO 2010127574, 2010 [Chem. Abstr. 2010, 1405570].
[5] Zhang, H.-M.; Cao, H.-J.; Zhang, Z.-Y.; Peng, J.-J.; Cui, H.-Y.; Zhang, T.-J.; Lei, G.-T. Chin. J. Org. Chem. 2012, 32, 621 (in Chinese). (张红梅, 曹湖军, 张志勇, 彭娟娟, 崔宏宇, 张天静, 雷钢铁, 有机化学, 2012, 32, 621.)
[6] Alonso-Vante, N.; Nierengarten, J.-F.; Sauvage, J.-P. J. Org. Chem. 1994, 4, 113.
[7] Thiruppathi, D.; Karuppasamy, P.; Ganesan, M.; Sivasubramanian, V. K.; Rajendran, T.; Rajagopal, S. Int. J. Chem. Kinet. 2014, 46, 606.
[8] Karnahl, M.; Mejía, E.; Rockstroh, N.; Tschierlei, S.; Luo, S.-P.; Grabow, K.; Kruth, A.; Brüser, V.; Junge, H.; Lochbrunner, S.; Beller, M. ChemCatChem 2014, 6, 82.

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新型1,10-菲咯啉衍生物的设计与合成

Design and Synthesis of Novel 1,10-Phenanthroline Derivatives

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