Synthesis, Structural Characterization and Catalytic Activity of Copper(I) Complexes with Triphenylphosphine and Pyridine Derivatives

摘要
图/表
参考文献
相关文章 (15)

全文: PDF (480 KB) HTML (1 KB)
输出: BibTeX | EndNote (RIS)

摘要

Two new Cu(I) complexes [CuCl(3-PyOH)(PPh3)2] (1) and [Cu2(μ-Cl)2(4- Stpy)(Ph3P)3] (2) (PyOH = hydroxypyridine; stpy = styrylpyridine) with triphenylphosphine and pyridine derivatives have been synthesized and characterized by elemental analysis and X-ray single-crystal diffraction. Compound 1 crystallizes in monoclinic, space group P21/c with a = 9.8945(7), b = 37.266(2), c = 10.9461(7) Å, β = 116.0750(10)°, V = 3625.3(4) Å3, Z = 4, Dc = 1.350 Mg/cm-3, μ = 0.801 mm-1, F(000) = 1528, the final R = 0.0320 and wR = 0.0729 for 18568 observed reflections (I > 2(I)), R(all data) = 0.0413, wR(all data) = 0.0769, completeness to theta of 25.01 is 99.9% and GOF = 1.037. Compound 2 crystallizes in monoclinic, space group P21/c with a = 11.290(3), b = 20.388(5), c = 24.092(6) Å, β = 102.028(4)°, V = 5424(2) Å3, Z = 4, Dc = 1.428 Mg/cm-3, μ = 1.016 mm-1, F(000) = 2408, the final R = 0.0568 and wR = 0.1486 for 27644 observed reflections (I > 2(I)), R(all data) = 0.0716, wR(all data) = 0.1592, completeness to theta of 25.01 is 99.9% and GOF = 1.056. Two new Cu(I) complexes have been utilized as catalysts for N-arylation of imidazole and both showed good catalytic activity.

	服务

	把本文推荐给朋友
	加入我的书架
	加入引用管理器
	E-mail Alert
	RSS
	作者相关文章
	刘桂艳
	徐颖
	刘成鑫

关键词 ： copper(I) complex, triphenylphosphine, pyridine derivatives, N-arylation, imidazole

Abstract：Two new Cu(I) complexes [CuCl(3-PyOH)(PPh3)2] (1) and [Cu2(μ-Cl)2(4- Stpy)(Ph3P)3] (2) (PyOH = hydroxypyridine; stpy = styrylpyridine) with triphenylphosphine and pyridine derivatives have been synthesized and characterized by elemental analysis and X-ray single-crystal diffraction. Compound 1 crystallizes in monoclinic, space group P21/c with a = 9.8945(7), b = 37.266(2), c = 10.9461(7) Å, β = 116.0750(10)°, V = 3625.3(4) Å3, Z = 4, Dc = 1.350 Mg/cm-3, μ = 0.801 mm-1, F(000) = 1528, the final R = 0.0320 and wR = 0.0729 for 18568 observed reflections (I > 2(I)), R(all data) = 0.0413, wR(all data) = 0.0769, completeness to theta of 25.01 is 99.9% and GOF = 1.037. Compound 2 crystallizes in monoclinic, space group P21/c with a = 11.290(3), b = 20.388(5), c = 24.092(6) Å, β = 102.028(4)°, V = 5424(2) Å3, Z = 4, Dc = 1.428 Mg/cm-3, μ = 1.016 mm-1, F(000) = 2408, the final R = 0.0568 and wR = 0.1486 for 27644 observed reflections (I > 2(I)), R(all data) = 0.0716, wR(all data) = 0.1592, completeness to theta of 25.01 is 99.9% and GOF = 1.056. Two new Cu(I) complexes have been utilized as catalysts for N-arylation of imidazole and both showed good catalytic activity.

Key words： copper(I) complex triphenylphosphine pyridine derivatives N-arylation imidazole

收稿日期: 2015-09-11 出版日期: 2016-05-12

基金资助:

Supported by the National Natural Science Foundation of China (NSFC 21102102)

通讯作者: guiyanliu2013@163.com E-mail: guiyanliu2013@163.com

引用本文:

刘桂艳;徐颖;刘成鑫. Synthesis, Structural Characterization and Catalytic Activity of Copper(I) Complexes with Triphenylphosphine and Pyridine Derivatives[J]. 结构化学, 2016, 35(5): 740-746.
LIU Gui-Yan;XU Ying;LIU Cheng-Xin . Synthesis, Structural Characterization and Catalytic Activity of Copper(I) Complexes with Triphenylphosphine and Pyridine Derivatives. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2016, 35(5): 740-746.

链接本文:

http://manu30.magtech.com.cn/jghx/CN/ 或 http://manu30.magtech.com.cn/jghx/CN/Y2016/V35/I5/740

REFERENCES
(1) Vohra, A. G.; Jannat, T. Cis and trans complexes of copper-I. Pak. J. Sci. Ind. Res. 1973, 16, 164–167.
(2) Sultana, N.; Arayne, M. S.; Irshad, A. K. Copper(I) complexes with triphenylphospbine and pyrazine. Ind. J. Chem. 1981, 20, 409–410.
(3) Sultana, N.; Arayne, M. S.; Mian, A. Copper(I) complexes with triphenylphosphine and quinoline. Kar. Univ. J. Sci.1988, 16, 39–48.
(4) Sultana, N.; Arayne, M. S.; Tabassum, H. Synthesis and characterization of copper(I) complexes of triphenylphospbine and 2-methylpyridine. Ind. J. Chem. 1994, 33A, 63–65.
(5) Sultana, N.; Arayne, M. S.; Mian, A. Copper(I) complexes of triphenylphosphine and dimethylaniline. Oriental. J. Chem. 1994, 10, 31–34.
(6) Sultana, N.; Arayne, M. S.; Tabassum, H. Copper(I) complexes of triphenylphosphine and aminophyridine. Rev. Roum. De Chimie. 1995, 40, 517–522.
(7) Sultana, N.; Arayne, M. S.; Tabassum, H. Synthesis and characterization of copper(I) complexes of triphenylphosphine and methylpyridine. Pak. J. Sci. Ind. Res. 1997, 40, 55–58.
(8) Yamamoto, T.; Ehara, Y.; Kubota, M.; Yamamoto, A. Preparation of copper(I)-phosphine complexes having Cu-N bonds and their reactions with organic halides. Bull. Chem. Soc. Jpn. 1980, 53, 1299–1302.
(9) Lobana, T. S.; Bhatia, P. K. Chemistry of mercaptopyridines and related ligands: part 1 synthesis and spectroscopic studies of complexes of copper(I) with 2(1H)-pyridinethione-S and tertiaryphosphines. Indian. J. Chem. Sect. A 1990, 29, 1225–1227.
(10) Mutrofin, S.; Chan, E. J.; Healy, P. C.; Marinelli, A.; Ngoune, J.; Pettinari, C.; Pettinari, R.; Somers, N.; Skelton, B. W.; White, A. H. Structural forms in complexes of 2,9-dimethyl-1,10-phenanthroline with simple salts of copper(I) and other univalent closed shell' species. Inorg. Chim. Acta 2008, 361, 2365–2374.
(11) He, L. H.; Chen, J. L.; Zhang, F.; Cao, X. F.; Tan, X. Z.; Chen, X. X.; Rong, G.; Luo, P.; Wen, H. R. Synthesis, characterization, and luminescence properties of mononuclear copper(I) halide complexes of 2-(2-benzimidazolyl)-6-methylpyridine. Inorg. Chem. Commun. 2012, 21, 125–128.
(12) Chen, J. L.; Cao, X. F.; Wang, J. Y.; He, L. H.; Liu, Z. Y.; Wen, H. R.; Chen, Z. N. Synthesis, characterization, and photophysical properties of heteroleptic copper(I) complexes with functionalized 3-(2΄-pyridyl)-1,2,4-triazole chelating ligands. Inorg. Chem. 2013, 52, 9727–9740.
(13) Engelhardt, L. M.; Healy, P. C.; Kildea, J. D.; White, A. H. Synthesis and structural characterization of binuclear μ,μ΄-dichloro-, dibromo- and diiodobis[(pyridine)(triphenylphosphine)copper(I)] complexes, and their pyridine-4-carbonitrile analogs. Aust. J. Chem. 1989, 42, 913–922.
(14) Bowmaker, G. A.; Hanna, J. V.; King, S. P.; Marchetti, F.; Pettinari, C.; Pizzabiocca, A.; Skelton, B. W.; Sobolev, A. N.; Tăbăcaru A.; White, A. H. Complexes of copper(I) thiocyanate with monodentate phosphine and pyridine Ligands and the P(N)-donor diphenyl(2-pyridyl) phosphine. Eur. J Inorg. Chem. 2014, 2014, 6104–6116.
(15) Meijboom, R.; Bowen, R. J.; Berners, P.; Susan, J. Coordination complexes of silver(I) with tertiary phosphine and related ligands. Coord. Chem. Rev. 2009, 253, 325–342.
(16) Singh, N. K.; Singh, M.; Tripathi, P.; Srivastava, A. K.; Butcher, R. J. Synthesis of a new N,N΄-ethane-1,2-bis(4-methoxyphenyl)carbothioamide ligand and its Cu(I) and Ag(I) complexes. Polyhedron 2008, 27, 375–382.
(17) Jin, Q. H.; Chen, L. M.; Yang, L.; Li, P. Z. The synthesis, structure and luminescence of two 1D pyrazine-connected Cu(I)-dppm polymers. Inorg. Chim. Acta 2009, 362, 1743–1748.
(18) Effendy.; Marchetti, F.; Pettinari, C.; Pettinari, R.; Skelton, B. W.; White, A. H. Synthesis and structural characterization of adducts of silver(I) oxyanion salts, AgX (X = ClO4, NO3), with Ph2E(CH2)xEPh2 (‘dpex’; E = P, As; x = 1～4) and oligodentate aromatic N-bases derivative of 2,2΄-bipyridyl, ‘L’, AgX:dpex:L (2:1:2). Inorg. Chim. Acta 2007, 360, 1388–1413.
(19) Nicola, C. D.; Effendy.; Fazaroh, F.; Pettinari, C.; Skelton, B. W.; Somers, N.; White, A. H. Structural characterization of 1:1 adducts of silver(I) (pseudo-) halides (AgX, X = NCO, Cl, Br, I) with Ph2E(CH2)EPh2 (E = P, As) (‘dp(p/a)m’) and 4:3 adducts of copper(I) halide (CuX, X = Cl, Br, I), containing trinuclear cations, of the form [X2Ag3(dppm)3]X and [X2Cu3(dppm)3](CuX2) and the novel neutral [(OCN)3Ag3(dpam)3]. Inorg. Chim. Acta 2005, 358, 720–734.
(20) Bowmaker, G. A.; Effendy.; Hanna, J. V.; Healy, P. C.; Skelton, B. W.; White, A. H. Crystal structures and spectroscopic studies of the mononuclear complex [AgBr(PPh3)2] and binuclear [Ag2X2(PPh3)4]•2CHCl3 (X = Cl or Br). J. Chem. Soc., Dalton Trans. 1993, 9, 1387–1397.
(21) Jin, Q. H.; Hu, K. Y.; Song, L. L.; Wang, R.; Zhang, C. L.; Zuo, X.; Lu, X. M. Synthesis and structural characterization of five copper(I) and silver(I) complexes with 2-aminopyridine (2-APy), [Cu(μ-Cl)(2-Apy)(PPh3)]2, [Ag(μ-X)(2-Apy)(PPh3)]2 (X = Cl, Br), [Ag(μ-ONO2)(2-Apy)(EPh3)]2 (E = P, As). Polyhedron 2010, 29, 441–445.
(22) Zhan, M. J.; Liu, X. H.; Zhang, Q. S.; Wang, B. X.; Cheng, Y. X.; Lu, C. Z. Synthesis, crystal structure and photophysical properties of Cu(I) complexes containing 2,5-bis(pyridyl)-1,3,4-oxadiazole. Chin. J. Struct. Chem. 2012, 31, 1145–1151.
(23) Ley, S. V.; Thomas, A. W. Modern synthetic methods for copper-mediated C(aryl)-O,C(aryl)-N, and C(aryl)-S bond formation. Angew. Chem. Int. Ed. 2003, 42, 5400–5449.
(24) Altman, R. A.; Kaval, E. D.; Buchwald, S. L. Copper-catalyzed N-arylation of imidazoles and benzimidazoles. J. Org. Chem. 2007, 72, 6190–6199.
(25) Verma, A. K.; Singh, J.; Sankar, V. K.; Chaudhary, R.; Chandra, R. Benzotriazole: an excellent ligand for Cu-catalyzed N-arylation of imidazoles with aryl and heteroaryl halides. Tetra. Lett. 2007, 49, 4207–4210.
(26) Priyarega, S.; Tamizh, M. M.; Babu, S. G.; Karvembu, R.; Natarajan, K. Copper(II) complexes with ONS donor ligand and triphenylphosphine: synthesis, characterization and catalytic applications. Indian J. Chem. 2012, 51A, 453–457.
(27) Zink, D. M.; Volz, D.; Baumann, T.; Mydlak, M.; Fluegge, H.; Friedrichs, J.; Nieger, M.; Brase, S. Heteroleptic, dinuclear copper(I) complexes for application in organic light-emitting diodes. Chem. Mat. 2013, 25, 4471–4486.
(28) Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. OLEX2: a complete structure solution, refinement and analysisprogram. J. Appl. Cryst. 2009, 2, 339–341.
(29) Sheldrick, G. M. SHELXL-97, Program for X-ray Crystal Structure Solution. University of Göttingen, Germany 1997.