Salen-Cu(II) Complex Catalyzed N-Arylation of Imidazoles under Mild Conditions

Yan Liu, Qin Zhang, Xiaowei Ma, Ping Liu, Jianwei Xie, Bin Dai, Zhiyong Liu

School of Chemistry and Chemical Engineering/Key Laboratory for Green Processin.
School of Chemistry and Chemical Engineering/Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, Shihezi University, Shihezi, China.

DOI: 10.4236/ijoc.2013.33023                

Abstract

Three inexpensive and air-/moisture-stable Salen-Cu complexes 1-3 were evaluated to be a novel class of catalysts for the N-arylation of imidazoles with aryl halides. A variety of aryl iodides, bromides underwent the coupling with imida-zoles, promoted by the complex 3, in moderate to excellent yields without the protection by an inert gas.

Keywords

Salen-Cu Complex; N-Arylation; Imidazole; Catalyze

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	C. Jacobs, M. Frotscher, G. Dannhardt and R. W. Hartmann, “1-Imidazolyl(alkyl)-Substituted Diand Tetrahy-droquinolines and Analogues: Syntheses and Evaluation of Dual Inhibitors of Thromboxane A2 Synthase and Aromatase,” Journal of Medicinal Chemistry, Vol. 43, No. 9, 2000, pp. 1841-1851. doi:10.1021/jm991180u
[2]	J. Zhong, “Muscarine, Imidazole, Oxazole and Thiazole Alkaloids,” Natural Product Reports, Vol. 22, No. 2, 2005, pp. 196-229. doi:10.1039/b316104h
[3]	C. Kison and T. Opatz, “Modular Synthesis of Tetrasubstituted Imidazoles and Trisubstituted Oxazoles by Aldimine Cross-Coupling,” Chemistry—A European Journal, Vol. 15, No. 4, 2009, pp. 843-845. doi:10.1002/chem.200802175
[4]	H. Gao and J. M. Shreeve, “Azole-Based Energetic Salts,” Chemical Reviews, Vol. 111, No. 11, 2011, pp. 7377-7436. doi:10.1021/cr200039c
[5]	S. Fujishima, R. Yasui, T. Miki, A. Ojida and I. Hamachi, “Ligand-Directed Acyl Imidazole Chemistry for Labeling of Membrane-Bound Proteins on Live Cells,” Journal of the American Chemical Society, Vol. 134, No. 9, 2012, pp. 3961-3964. doi:10.1021/ja2108855
[6]	D. Enders, O. Niemeier and A. Henseler, “Organocatalysis by N-Heterocyclic Carbenes,” Chemical Reviews, Vol. 107, No. 2, 2007, pp. 5606-5655. doi:10.1021/cr068372z
[7]	L. Benhamou, E. Chardon, G. Lavigne, S. BelleminLaponnaz and V. César, “Synthetic Routes to N-Heterocyclic Carbene Precursors,” Chemical Reviews, Vol. 111, No. 4, 2011, pp. 2705-2733. doi:10.1021/cr100328e
[8]	F. Monnier and M. Taillefer, “Catalytic C-C C-N, and C-O Ullmann-Type Coupling Reactions,” Angewandte Chemie International Edition, Vol. 48, No. 38, 2009, pp. 6954-6971.doi:10.1002/anie.200804497
[9]	D. S. Surry and S. L. Buchwald, “Dialkylbiaryl Phosphines in Pd-Catalyzed Amination: A User’s Guide,” Chemical Science, Vol. 2, No. 1, 2011, pp. 27-50.
[10]	D. Maiti, B. P. Fors, J. L. Henderson, Y. Nakamura and S. L. Buchwald, “Palladium-Catalyzed Coupling of Functionalized Primary and Secondary Amines with Aryl and Heteroaryl Halides: Two Ligands Suffice in Most Cases,” Chemical Science, Vol. 2, No. 1, 2011, pp. 57-68. doi:10.1039/c0sc00330a
[11]	S. L. Buchwald, A. Klapars, J. C. Antilla, G. E. Job, M. Wolter, F. Y. Kwong, G. Nordmann and E. J. Hennessy, “Copper-Catalyzed Formation of Carbon-Heteroatom and Carbon-Carbon Bonds,” US 2001 0286286-WO02/085838.
[12]	A. Klapars, J. C. Antilla, X. Huang and S. L. Buchwald, “A General And Efficient Copper Catalyst for the Amidation of Aryl Halides and the N-Arylation of Nitrogen Heterocycle,” Journal of the American Chemical Society, Vol. 123, No. 31, 2001, pp. 7727-7729. doi:10.1021/ja016226z
[13]	M. Taillefer, H.-J. Cristau, P. P. Cellier, J.-F. Spindler and A. Ouali, “Method for Forming a Carbon-Carbon or Carbon-Heteroatom Linkage,” Fr 2001, 16547-WO035 3225.
[14]	A. Klapars, X. Huang and S. L. Buchwald, “A General and Efficient Copper Catalyst for the Amidation of Aryl Halides,” Journal of the American Chemical Society, Vol. 124, No. 25, 2002, pp. 7421-7428. doi:10.1021/ja0260465
[15]	Z. Lu and R. Twieg, “Copper-Catalyzed Aryl Amination in Aqueous Media with 2-Dimethylaminoethanol Ligand,” Tetrahedron Lettersers, Vol. 46, No. 17, 2005, pp. 2997-3001. doi:10.1016/j.tetlet.2005.03.027
[16]	H. Rao, H. Fu, Y. Jiang and Y. Zhao, “Copper-Catalyzed Arylation of Amines Using Diphenyl Pyrrolidine-2-Phosphonate as the New Ligand,” The Journal of Organic Chemistry, Vol. 70, No. 20, 2005, pp. 8107-8109. doi:10.1021/jo051221w
[17]	H. Zhang, Q. Cai and D. Ma, “Amino Acid Promoted CuI-Catalyzed C-N Bond Formation between Aryl Halides and Amines or N-Containing Heterocycles,” The Journal of Organic Chemistry, Vol. 70, No. 13, 2005, pp. 5164-5173. doi:10.1021/jo0504464
[18]	Y. Chen and H. Chen, “1,1,1-Tris(hydroxymethyl)ethane as A New, Efficient, and Versatile Tripod Ligand for Copper-Catalyzed Cross-Coupling Reactions of Aryl Iodides with Amides, Thiols, and Phenols,” Organic Letters, Vol. 8, No. 24, 2006, pp. 5609-5612. doi:10.1021/ol062339h
[19]	M. Yang and F. Liu, “Diamine Ligands in Copper-Catalyzed Reactions, An Ullmann Coupling of Aryl Iodides and Amines Using An Air-Stable Diazaphospholane Ligand,” The Journal of Organic Chemistry, Vol. 72, No. 23, 2007, pp. 8969-8971. doi:10.1021/jo0712291
[20]	P. Suresh and K. Pitchumani, “Per-6-amino-β-cyclodextrin as An Efficient Supramolecular Ligand and Host for Cu(I)-Catalyzed N-Arylation of Imidazole with Aryl Bromides,” The Journal of Organic Chemistry, Vol. 73, No. 22, 2008, pp. 9121-9124. doi:10.1021/jo801811w
[21]	D. Wang and K. Ding, “2-Pyridinyl β-Ketones as New Ligands for Room-Temperature CuI-Catalysed C-N Coupling Reactions,” Chemical Communications, No. 14, 2009, pp. 1891-1893. doi:10.1039/b821212k
[22]	H. Zhao, H. Fu and R. Qiao, “Copper-Catalyzed Direct Amination of Ortho-Functionalized Haloarenes with Sodium Azide as the Amino Source,” The Journal of Organic Chemistry, Vol. 75, No. 10, 2010, pp. 3311-3316. doi:10.1021/jo100345t
[23]	K. G. Thakur, K. S. Srinivas, K. Chiranjeevi and G. Sekar, “D-Glucosamine as An Efficient Ligand for the CopperCatalyzed Selective Synthesis of Anilines from Aryl Halides and NaN3,” Green Chemistry, Vol. 13, No. 9, 2011, pp. 2326-2329. doi:10.1039/c1gc15469a
[24]	D. Wang, F. Zhang, D. Kuang, J. Yu and J. Li, “A Highly Efficient Cu-Catalyst System for N-Arylation of Azoles in Water,” Green Chemistry, Vol. 14, No. 5, 2012, pp. 1268-1271. doi:10.1039/c2gc35077g
[25]	Z. Q. Wu, Z. Q. Jiang, D. Wu, H. F. Xiang and X. G. Zhou, “A Simple and Efficient Catalytic System for Coupling Aryl Halides with Aqueous Ammonia in Water,” European Journal of Organic Chemistry, Vol. 2010, No. 10, 2010, pp. 1854-1857. doi:10.1002/ejoc.201000060
[26]	Z. Q. Wu, L. Zhou, Z. Q. Jiang, D. Wu, Z. K. Li and X. G. Zhou, “Sulfonato-Cu(salen) Complex Catalyzed N-Arylation of Aliphatic Amines with Aryl Halides in Water,” European Journal of Organic Chemistry, Vol. 2010, No. 26, 2010, pp. 4971-4975. doi:10.1002/ejoc.201000840
[27]	Y. Wang, Z. Wu, L. X. Wang, Z. K. Li and X. G.Zhou, “A Simple and Efficient Catalytic System for N-Arylation of Imidazoles in Water,” Chemistry—A European Journal, Vol. 15, No. 36, 2009, pp. 8971-8974. doi:10.1002/chem.200901232
[28]	Y. L. Jiao, N. N. Yan, J. W. Xie, X. W. Ma, P. Liu and B. Dai, “A Simple and Efficient Copper(II) Complex as a Catalyst for N-Arylation of Imidazoles,” Chinese Journal of Chemistry, Vol. 31, No. 2, 2013, pp. 267-270. doi:10.1002/cjoc.201201121
[29]	P. Liu, X.-J. Feng and R. He, “Salen and Half-Salen Palladium(Ii) Complexes: Synthesis, Characteriztion and Catalytic Activity toward Suzuki—Miyaura Reaction,” Tetrahedron, Vol. 66, No. 3, 2010, pp. 631-636. doi:10.1016/j.tet.2009.11.072
[30]	N. I. Giricheva, G. V. Girichev, N. P. Kuzmina, Y. S. Medvedeva, A. Y. Rogachev, “Structure of the Cu(Salen) Molecule, CuO2N2C16H14, According to Gas-Phase Electron Diffraction Data and Quantum Chemical Calculations,” Journal of Structural Chemistry, Vol. 50, No. 1, 2009, pp. 52-59. doi:10.1007/s10947-009-0007-1
[31]	Y. N. Belokon, R. G. Davies, J. A. Fuentes and M. North, “The Influence of Imine Structure, Catalyst Structure and Reaction Conditions on the Enantioselectivity of the Alkylation of Alanine Methyl Ester Imines Catalyzed by Cu(ch-salen),” Tetrahedron Letters, Vol. 42, No. 45, 2001, pp. 8093-8096. doi:10.1016/S0040-4039(01)01718-X
[32]	Y. L. Wen, W. Huang, B. Wang, J. C. Fan, Z. H. Gao and L. H. Yin, “Synthesis of Salicylaldehyde Schiff Base Modified Cu Nanocrystals by Thermal Treatment in Liquid Paraffin,” Applied Surface Science, Vol. 258, No. 2, 2011, pp. 946-949. doi:10.1016/j.apsusc.2011.09.033
[33]	Y. N. Belokon, M. North, T. D. Churkina, N. S. Ikonnikova and V. I. Maleev, “Chiral Salen-Metal Complexes as Novel Catalysts for the Asymmetric Synthesis of A-Amino Acids under Phase Transfer Catalysis Conditions,” Tetrahedron, Vol. 57, No. 13, 2001, pp. 2491-2498. doi:10.1016/S0040-4020(01)00072-2
[34]	S. Sabarinathan, G. Vasuki, P. S. Rao, “Chiral Cu(II) Salen Complexes Catalyzed Aerobic Oxidative Biaryl Coupling Probing the Reaction by EPR,” Chemistry—A European Journal, Vol. 1, No. 4, 2010, pp. 360-367. doi:10.5155/eurjchem.1.4.360-367.221
[35]	M. G. B. Drew, J. F. Godsell, S. Roy, G. Mukhopadhyay and D. Maity, “Synthesis and Characterization of Cu(II) Complexes of Tetradentate and Tridentate Symmetrical Schiff Base Ligands Involving O-Phenelenediamine, Salicylaldehyde and Diacetylmonoxime,” Transition Metal Chemistry, Vol. 35, No. 2, 2010, pp. 197-204. doi:10.1007/s11243-009-9314-9
[36]	M. M. Abd-Elzaher, “Synthesis and Spectroscopic Characterization of Some Tetadentate Schiff Bases and Their Nickel, Copper and Zinc Complexes,” Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, Vol. 30, No. 9, 2000, pp. 1805-1816.
[37]	M. Salavati-Niasari, M. Shakouri-Arani and F. Davar, “Flexible Ligand Synthesis, Characterization and Catalytic Oxidation of Cyclohexane with Host (Nanocavity of zeoLite-Y)/Guest (Mn(II), Co(II), Ni(II) and Cu(II) Complexes of Tetrahydro-salophen) Nanocomposite Materials,” Microporous Mesoporous Mater, Vol. 116, No. 1-3, 2008, pp. 77-85. doi:10.1016/j.micromeso.2008.03.015
[38]	M. Taillefer, N. Xia and A. Ouali, “Efficient Iron/Copper Co-Catalyzed Arylation of Nitrogen Nucleophiles,” Angewandte Chemie International Edition, Vol. 46, No. 6, 2007, pp. 934-936.doi:10.1002/anie.200603173
[39]	H.-C. Ma and X.-Z. Jiang, “N-Hydroxyimides as Efficient Ligands for the Copper-Catalyzed N-Arylation of Pyrrole, Imidazole, and Indole,” The Journal of Organic Chemistry, Vol. 72, No. 23, 2007, pp. 8943-8946. doi:10.1021/jo7015983
[40]	J. P. Collman, M. Zhong, L. Zeng and S. Costanzo, “The [Cu(OH).TMEDA]2Cl2-Catalyzed Coupling of Arylboronic Acids with Imidazoles in Water,” The Journal of Organic Chemistry, Vol. 66, No. 4, 2001, pp. 1528-1531. doi:10.1021/jo0016780