Ligand assisted copper-catalyzed Ullmann cross coupling reaction of bromaminic acid with amines

doi:10.1016/j.cjche.2016.01.010

›› 2016, Vol. 24 ›› Issue (8): 1000-1006.DOI: 10.1016/j.cjche.2016.01.010

• Catalysis, Kinetics and Reaction Engineering • Previous Articles Next Articles

Ligand assisted copper-catalyzed Ullmann cross coupling reaction of bromaminic acid with amines

Beibei Shao, Hongying Du, Xinyu Hao, Rongwen Lu, Yi Luo, Shufen Zhang

State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China

Received:2015-12-03 Revised:2016-01-05 Online:2016-09-21 Published:2016-08-28
Supported by:
Supported by the National Natural Science Foundation of China (21176038, 21576044, 21536002), the Science Fund for Creative Research Groups of the National Natural Science Foundation of China (21421005) and the Dalian University of Technology Innovation Team (DUT2013TB07).

Ligand assisted copper-catalyzed Ullmann cross coupling reaction of bromaminic acid with amines

Beibei Shao, Hongying Du, Xinyu Hao, Rongwen Lu, Yi Luo, Shufen Zhang

State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China

通讯作者: Rongwen Lu
基金资助:
Supported by the National Natural Science Foundation of China (21176038, 21576044, 21536002), the Science Fund for Creative Research Groups of the National Natural Science Foundation of China (21421005) and the Dalian University of Technology Innovation Team (DUT2013TB07).

Abstract

Abstract: Three types of ligands have been developed for copper-catalyzed Ullmann cross coupling reaction of bromaminic acid with amines in aqueous solution. Ligands with large steric hindrance and strong electron-donating capacity were beneficial to the reaction. UV-Vis and CV analyses demonstrated that these ligands had strong coordination with copper(I), implying the effect of ligand coordination ability on the stability and catalytic activity of catalytic system.

Key words: Bromaminic acid, Ullmann cross coupling reaction, Ligand, Copper catalysis

摘要： Three types of ligands have been developed for copper-catalyzed Ullmann cross coupling reaction of bromaminic acid with amines in aqueous solution. Ligands with large steric hindrance and strong electron-donating capacity were beneficial to the reaction. UV-Vis and CV analyses demonstrated that these ligands had strong coordination with copper(I), implying the effect of ligand coordination ability on the stability and catalytic activity of catalytic system.

关键词: Bromaminic acid, Ullmann cross coupling reaction, Ligand, Copper catalysis

Beibei Shao, Hongying Du, Xinyu Hao, Rongwen Lu, Yi Luo, Shufen Zhang. Ligand assisted copper-catalyzed Ullmann cross coupling reaction of bromaminic acid with amines[J]. , 2016, 24(8): 1000-1006.

References

[1] K. Kunz, U. Scholz, D. Ganzer, Renaissance of Ullmann and Goldberg reactions-Progress in copper catalyzed C-N-, C-O- and C-S-coupling, Synlett 2428(2003).
[2] J.R.H. Ross, Ullmann's encyclopedia of industrial chemistry, fifth edition, volume A1, Appl. Catal. 21(1986) 213.
[3] F. Monnier, M. Taillefer, Catalytic C-C, C-N, and C-O Ullmann-type coupling reactions, Angew. Chem. Int. Ed. 48(2009) 6954.
[4] Z. Vrba, Mechanism of the Ullmann condensation, Collect. Czechoslov. Chem. Commun. 46(1981) 92.
[5] I.P. Beletskaya, A.V. Cheprakov, The complementary competitors:Palladium and copper in C-N cross-coupling reactions, Organometallics 31(2012) 7753.
[6] P.F. Larsson, A. Correa, M. Carril, P.-O. Norrby, C. Bolm, Copper-catalyzed crosscouplings with part-per-million catalyst loadings, Angew. Chem. 121(2009) 5801.
[7] A. Shafir, P.A. Lichtor, S.L. Buchwald, N-versus O-arylation of aminoalcohols:Orthogonal selectivity in copper-based catalysts, J. Am. Chem. Soc. 129(2007) 3490.
[8] L. Liang, Z. Li, X. Zhou, Pyridine N-oxides as ligands in Cu-catalyzed N-arylation of imidazoles in water, Org. Lett. 11(2009) 3294.
[9] H.J. Xu, F.Y. Zheng, Y.F. Liang, Z.Y. Cai, Y.S. Feng, D.Q. Che, Ligand-free CuCl-catalyzed C-N bond formation in aqueous media, Tetrahedron Lett. 51(2010) 669.
[10] J. Jiao, X.R. Zhang, N.H. Chang, J. Wang, J.F. Wei, X.Y. Shi, Z.G. Chen, A facile and practical copper powder-catalyzed, organic solvent- and ligand-free Ullmann amination of aryl halides, J. Org. Chem. 76(2011) 1180.
[11] T.D. Tuong, M. Hida, A novel catalyst system for the Ullmann condensation in aqueous solution. Reaction of a halogenoanthraquinone with aniline, Chem. Lett. 363(1973).
[12] Y. Baqi, C.E. Muller, Rapid and efficient microwave-assisted copper(0)-catalyzed Ullmann coupling reaction:General access to anilinoanthraquinone derivatives, Org. Lett. 9(2007) 1271.
[13] H. Rao, Y. Jin, H. Fu, Y. Jiang, Y. Zhao, A versatile and efficient ligand for coppercatalyzed formation of C-N, C-O, and P-C bonds:Pyrrolidine-2-phosphonic acid phenyl monoester, Chem. Eur. J. 12(2006) 3636.
[14] R. Menif, A.E. Martell, P.J. Squattrito, A. Clearfield, New hexaaza macrocyclic binucleating ligands. Oxygen insertion with a dicopper(I) Schiff base macrocyclic complex, Inorg. Chem. 29(1990) 4723.
[15] A. Vijayaraj, R. Prabu, R. Suresh, C. Sivaraj, N. Raaman, V. Narayanan, New acyclic Schiff-base copper(Ⅱ) complexes and their electrochemical, catalytic, and antimicrobial studies, J. Coord. Chem. 64(2011) 637.
[16] H. Naeimi, M. Moradian, Encapsulation of copper(I)-Schiff base complex in NaY nanoporosity:An efficient and reusable catalyst in the synthesis of propargylamines via A3-coupling (aldehyde-amine-alkyne) reactions, Appl. Catal. A Gen. 467(2013) 400.
[17] F. Rafat, K.S. Siddiqi, Synthesis and physicochemical properties of Schiff base Macrocyclic ligands and their transition metal chelates, J. Korean Chem. Soc. 55(2011) 912.
[18] F. Rafat, K.S. Siddiqi, Synthesis and physicochemical properties of Schiff base macrocyclic ligands and their transition metal chelates, J. Korean Chem. Soc. 55(2011) 912.
[19] G. De Santis, L. Fabbrizzi, M. Licchelli, C. Mangano, P. Pallavicini, The copper(I) complex of a metallocyclam-functionalized phenanthroline:A poorly stable species that is very resistant to oxidation, Inorg. Chem. 32(1993) 3385.
[20] O. Carugo, C.B. Castellani, Five-co-ordinated copper(Ⅱ) complexes:A new look at the isomerization from trigonal-bipyramidal to square-pyramidal geometry in bis(bipyridyl)-(monodentate ligand)copper(Ⅱ) and related complexes, J. Chem. Soc. Dalton Trans. 2895(1990).
[21] K. Yang, Y. Qiu, Z. Li, Z. Wang, S. Jiang, Ligands for copper-catalyzed C-N bond forming reactions with 1 mol% CuBr as catalyst, J. Org. Chem. 76(2011) 3151.
[22] J.W. Tye, Z. Weng, A.M. Johns, C.D. Incarvito, J.F. Hartwig, Copper complexes of anionic nitrogen ligands in the amidation and imidation of aryl halides, J. Am. Chem. Soc. 130(2008) 9971.
[23] S. Itoh, Y. Hashimoto, S. Fukuzumi, Reaction of Cu(I) complexes bearing a phenol group in the ligand with O2, Appl. Catal. A Gen. 194-195(2000) 453.
[24] M. Boiocchi, L. Fabbrizzi, Double-stranded dimetallic helicates:Assemblingdisassembling driven by the Cu(I)/Cu(Ⅱ) redox change and the principle of homochiral recognition, Chem. Soc. Rev. 43(2014) 1835.

Ligand assisted copper-catalyzed Ullmann cross coupling reaction of bromaminic acid with amines

Ligand assisted copper-catalyzed Ullmann cross coupling reaction of bromaminic acid with amines

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 6

Recommended Articles

Metrics

Comments

[1]	Yi Shen, Xinshuang Chu, Qinghong Shi. Unraveling structure and performance of protein a ligands at liquid–solid interfaces: A multi-techniques analysis [J]. Chinese Journal of Chemical Engineering, 2023, 54(2): 232-239.
[2]	Qinghong Shi, Yan Sun. Protein A-based ligands for affinity chromatography of antibodies [J]. Chinese Journal of Chemical Engineering, 2021, 29(2): 194-203.
[3]	Jia Ju, Feixue Liang, Xiaoxin Zhang, Ran Sun, Xiaoguang Pan, Xiaoyun Guan, Guanning Cui, Xuan He, Mengyan Li. Advancement in separation materials for blood purification therapy [J]. Chinese Journal of Chemical Engineering, 2019, 27(6): 1383-1390.
[4]	Xiaolong Xu, Haihua He, Jia Zhao, Bailin Wang, Shanchuan Gu, Xiaonian Li. The ligand coordination approach for improving the stability of low-mercury catalyst in the hydrochlorination of acetylene [J]. , 2017, 25(9): 1217-1221.
[5]	Ping Wen, Kewen Tang, Jicheng Zhou, Panliang Zhang. Simulation and analysis of multi-stage centrifugal fractional extraction process of 4-nitrobenzene glycine enantiomers [J]. Chin.J.Chem.Eng., 2015, 23(11): 1774-1781.
[6]	ZHU Yuju, ZHOU Jianhai, HU Jun, LIU Honglai, HU Ying. Computer Simulation of Adsorption and Separation of CO₂/CH₄ in Modified COF-102 [J]. Chin.J.Chem.Eng., 2011, 19(5): 709-716.