A New Palladium Complex Containing the Mixture of Carbene and Phosphine Ligands: Synthesis,Crystal Structure and Spectral FT-IR,NMR and UV-Vis Researches

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In this paper, a new Pd-based complex that contains N-heterocyclic carbene (NHC) and triphenylphosphine (PPh3) ligands was synthesized. The cis-(NHC)PdBr2(PPh3) complex has been prepared by the substitution of 3-chloropyridine ligand in (NHC)PdBr2(3-chloropyridine) complex with triphenylphosphine. This complex has been characterized by using 1H NMR, 31P {1H} NMR, 13C {1H} NMR, FTIR, UV-Vis spectroscopy and elemental analysis techniques. The molecular and crystal structures of the cis-(NHC)PdBr2(PPh3) complex were determined by single-crystal X-ray diffraction method.

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	AydIn
	AktaS

关键词 ： FTIR, N-heterocyclic carbene, NMR, UV-VIS, X-ray diffraction

Abstract：In this paper, a new Pd-based complex that contains N-heterocyclic carbene (NHC) and triphenylphosphine (PPh3) ligands was synthesized. The cis-(NHC)PdBr2(PPh3) complex has been prepared by the substitution of 3-chloropyridine ligand in (NHC)PdBr2(3-chloropyridine) complex with triphenylphosphine. This complex has been characterized by using 1H NMR, 31P {1H} NMR, 13C {1H} NMR, FTIR, UV-Vis spectroscopy and elemental analysis techniques. The molecular and crystal structures of the cis-(NHC)PdBr2(PPh3) complex were determined by single-crystal X-ray diffraction method.

Key words： FTIR N-heterocyclic carbene NMR UV-VIS X-ray diffraction

收稿日期: 2019-01-31 出版日期: 2019-10-12

基金资助:The author thank the ?nönü University Scientific and Technology Center for the FT-IR, 1H NMR, 31P NMR, 13C NMR, elemental analysis and UV-Vis spectroscopy of the complex, and the Dokuz Eylül University for the use of Oxford Rigaku Xcalibur Eos Diffractometer (purchased under University Research Grant No: 2010.KB.FEN.13)

通讯作者: aydinaktash@hotmail.com E-mail: aydinaktash@hotmail.com

引用本文:

AydIn;AktaS. A New Palladium Complex Containing the Mixture of Carbene and Phosphine Ligands: Synthesis,Crystal Structure and Spectral FT-IR,NMR and UV-Vis Researches[J]. 结构化学, 2019, 38(10): 1664-1672.
AydIn;AktaS. A New Palladium Complex Containing the Mixture of Carbene and Phosphine Ligands: Synthesis,Crystal Structure and Spectral FT-IR, #br# NMR and UV-Vis Researches. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2019, 38(10): 1664-1672.

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http://manu30.magtech.com.cn/jghx/CN/ 或 http://manu30.magtech.com.cn/jghx/CN/Y2019/V38/I10/1664

REFERENCES
(1) Alcarazo, M.; Stork, T.; Anoop, A.; Thiel, W.; Fürstner, A. Steering the surprisingly modular π‐acceptor properties of N‐heterocyclic carbenes: implications for gold catalysis. Angew Chem. Int. Ed. 2010, 49, 25422546.
(2) Buscemi, G.; Basato, M.; Biffis, A.; Gennaro, A.; Isse, A. A.; Natile, M. M.; Tubaro, C. Electronic properties of chelating dicarbene palladium complexes: a combined electrochemical, NMR and XPS investigation. J. Organomet. Chem. 2010, 695, 23592365.
(3) Hopkinson, M. N.; Richter, C.; Schedler, M.; Glorius, F. An overview of N-heterocyclic carbenes. Nature 2014, 510, 485496.
(4) Lazreg, F.; Nahra, F.; Cazin, C. S. J. Copper-NHC complexes in catalysis. Coord. Chem. Rev. 2015, 293, 4879.
(5) Nelson, D. J.; Nolan, S. P. Quantifying and understanding the electronic properties of N-heterocyclic carbenes. Chem. Soc. Rev. 2013, 42, 67236753.
(6) Liu, N.; Luo, F.; Wu, H.; Liu, Y.; Zhang, C. One‐step ıonic‐liquid‐assisted electrochemical synthesis of ıonic‐liquid‐functionalized graphene sheets directly from graphite. Adv. Funct. Mater. 2008, 18, 15181525.
(7) Valentine, D. H.; Hillhouse, J. H. Electron-rich phosphines in organic synthesis II. Catalytic applications. Synthesis 2003, 16, 24372460.
(8) Christmann, U.; Vilar, R. Monoligated palladium species as catalysts in cross‐coupling reactions. Angew Chem. Int. Ed. 2005, 44, 366374.
(9) Lee, M. T.; Hu, C. H. Density functional study of N-heterocyclic and diamino carbene complexes: comparison with phosphines. Organometallics 2004, 23, 976983.
(10) Herrmann, W. A.; Öfele, K.; Elison, M.; Kühn, F. E.; Roesky, P. W. Nucleophilic cyclocarbenes as ligands in metal halides and metal oxides. J. Organomet. Chem. 1994, 480, c7c9.
(11) Crabtree, R. H. NHC ligands versus cyclopentadienyls and phosphines as spectator ligands in organometallic catalysis. J. Organomet. Chem. 2005, 690 54515457.
(12) Gaillard, S.; Renaud, J. L. When phosphorus and NHC (N-heterocyclic carbene) meet each other. Dalton Trans. 2013, 42, 72557270.
(13) Bestgen, S.; Gamer, M. T.; Lebedkin, S.; Kappes, M. M.; Roesky, P. W. Di‐ and trinuclear gold complexes of diphenylphosphinoethyl‐functionalised ımidazolium salts and their N‐heterocyclic carbenes: synthesis and photophysical properties. Chem.-Eur. J. 2015, 21, 601614.
(14) Guo, C.; Janssen-Müller, D.; Fleige, M.; Lerchen, A. G.; Daniliuc, C.; Glorius, F. Mechanistic studies on a cooperative nhc organocatalysis/palladium catalysis system: uncovering significant lessons for mixed chiral Pd(NHC)(PR3) catalyst design. J. Am. Chem. Soc. 2017, 139, 4443−4451.
(15) Jin, H.; Kluth, P.; Hahn, F. E. Synthesis of complexes with protic NH, NR-NHC ligands by oxidative addition of N-alkyl-2-iodoimidazoles to [M(PPh3)4] (M = Pd, Pt) complexes. Eur. J. Inorg. Chem. 2017, 2774–2781.
(16) Herrmann, W. A. A new concept in organometallic catalysis. Angew Chem. Int. Ed. 2002, 41, 12901309.
(17) Marion, N.; Nolan, S. P.; Marion, N.; Nolan, S. P. Well-defined N-heterocyclic carbenes-palladium(II) precatalysts for cross-coupling reactions. Acc Chem. Res. 2008, 41, 14401449.
(18) Poyatos, M.; Mata, J. A.; Peris, E. Complexes with poly(N-heterocyclic carbene) ligands: structural features and catalytic applications. Chem. Rev. 2009, 109, 36773707.
(19) Diez-Gonzalez, S.; Marion, N.; Nolan, S. P. N-heterocyclic carbenes in late transition metal catalysis. Chem. Rev. 2009, 109, 36123676.
(20) Hu, X.; Castro-Rodriguez, I.; Olsen, K.; Meyer, K. Group 11 metal complexes of n-heterocyclic carbene ligands: nature of the metal carbene bond. Organometallics 2004, 23, 755764.
(21) Süssner, M.; Plenio, H. π-Face donor properties of N-heterocyclic carbenes. Chem. Commun. 2005, 43, 54175419.
(22) Cavallo, L.; Correa, A.; Costabile, C.; Jacobsen, H. Steric and electronic effects in the bonding of N-heterocyclic ligands to transition metals. J Organomet. Chem. 2005, 690 54075413.
(23) Liao, C. Y.; Chan, K. T.; Tu, C. Y.; Chang, Y. W.; Hu, C. H.; Lee, H. M. Robust and electron‐rich cis‐palladium(II) complexes with phosphine and carbene ligands as catalytic precursors in suzuki coupling reactions. Chem. Eur. J. 2009, 15, 405417.
(24) Aktaş, A.; Barut Celepci, D.; Gök, Y.; Aygün, M. 2-Hydroxyethyl-substituted (NHC)Pd(II)PPh3 complexes: synthesis, characterization, crystal structure and ıts application on sonogashira cross-coupling reactions in aqueous media. Chem. Select. 2018, 3, 1093210937.
(25) Aktaş, A.; Erdemir, F.; Barut Celepci, D.; Gök, Y.; Aygün, M. Mixed phosphine/n‑heterocyclic carbene-palladium complexes: synthesis, characterization, crystal structure and application in the Sonogashira reaction in aqueous media. Transit. Metal Chem. 2019, 44, 229236.
(26) Boubakri, L.; Yaşar, S.; Dorcet, V.; Roisnel, T.; Bruneau, C.; Hamdi, N.; Özdemir, İ. Synthesis and catalytic applications of palladium N-heterocyclic carbene complexes as efficient pre-catalysts for Suzuki-Miyaura and Sonogashira coupling reactions. New J. Chem. 2017, 41, 51055113.
(27) Dehimat, Z. I.; Yaşar, S.; Tebbani, D.; Özdemir, İ. Sonogashira cross-coupling reaction catalyzed by N-heterocyclic carbene-Pd(II)-PPh3 complexes under copper free and aerobic conditions. Inorg. Chim. Acta 2018, 469, 325334.
(28) Touj, N.; Yaşar, S.; Özdemir, N.; Hamdi, N.; Özdemir, İ. Sonogashira cross-coupling reaction catalysed by mixed NHC-Pd-PPh3 complexes under copper free conditions. J. Organomet. Chem. 2018, 860, 5971.
(29) Chan, K. T.; Tsai, Y. H.; Lin, W. S.; Wu, J. R.; Chen, S. J.; Liao, F. X.; Hu, C. H.; Lee, H. M. Palladium complexes with carbene and phosphine ligands: synthesis, structural characterization, and direct arylation reactions between aryl halides and alkynes. Organometallics 2010, 29, 463472.
(30) Herrmann, W. A.; Böhm, V. P. W.; Gstöttmayr, C. W. K.; Grosche, M.; Reisinger, C. P.; Weskamp, T. Synthesis, structure and catalytic application of palladium(II) complexes bearing N-heterocyclic carbenes and phosphines. J. Organomet. Chem. 2001, 617618, 616628.
(31) Zhang, J.; Xu, J.; Xu, Y.; Sun, H.; Shen, Q.; Zhang, Y. Mixed NHC/phosphine Ni(II) complexes: synthesis and their applications as versatile catalysts for selective cross-couplings of armgx with aryl chlorides, fluorides, and methyl ethers. Organometallics 2015, 34, 57925800.
(32) Diebolt, O.; Jurčík, V.; Correa da Costa, R.; Braunstein, P.; Cavallo, L.; Nolan, S. P.; Slawin, A. M. Z.; Cazin, C. S. J. Mixed phosphite/N-heterocyclic carbene complexes: synthesis, characterization and catalytic studies. Organometallics 2010, 29, 1443450.
(33) CrysAlisPro Software System, Version 1.171.38.43, Rigaku Corporation, Oxford, UK 2015.
(34) Clark, R. C.; Reid. J. S. The analytical calculation of absorption in multifaceted crystals. Acta Cryst. 1995, A51, 887897.
(35) Sheldrick, G. M. SHELXT-integrated space-group and crystal-structure determination. Acta Cryst. 2015, A71, 38.
(36) Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Cryst. 2015, C71, 38.
(37) Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. 2009, 42, 339341.
(38) Kılıç, A.; Tas, E.; Gumgum, B.; Yılmaz, İ. Synthesis, spectroscopic and electrochemical investigations of two vic-dioximes and their mononuclear Ni(II), Cu(II) and Co(II) metal complexes containing morpholine group. Chin. J. Chem. 2006, 24, 159916004.
(39) Sacconi, L.; Ciampolini, M.; Maffio, F.; Cavasino, F. P. Studies in coordination chemistry. IX.1 investigation of the stereochemistry of some complex compounds of cobalt(II) with N-substituted salicylaldimines. J. Am. Chem. Soc. 1962, 84, 32453248.
(40) Kılıç, A.; Tas, E.; Yılmaz, İ. Synthesis, spectroscopic and redox properties of the mononuclear NiII, NiII(BPh2)2 containing (B-C) bond and trinuclear CuII-NiII-CuII type-metal complexes of N,N΄-(4-amino-1-benzyl piperidine)-glyoxime. J. Chem. Sci. 2009, 121, 4356.
(41) Devkule, S. S.; More, M. S.; Chavan, S. S. Synthesis, characterization, luminescence and catalytic properties of copper(I) complexes with N-(2-pyridylmethylene)-1,5-dimethyl-2-pyrazole-3-(2H)-one and triphenylphosphine as ligands. Inorg. Chim. Acta 2017, 455, 183–189.
(42) Mrad, M. L.; Feddaoui, I.; Abdelbaky, M. S. M.; García-Granda, S.; Ben Nasr, C. Synthesis, crystal structure, vibrational and optical properties of a new Pb(II) complex (2-hydroxyethyl)piperazine-1,4-diium tetrachloroplombate(II) C6H16N2OPbCl4. Inorg. Chim. Acta 2018, 476, 3845.
(43) Baltog, I.; Baibarac, M.; Lefrant, S. Quantum well effect in bulk PbI2 crystals revealed by the anisotropy of photoluminescence and Raman spectra. J. Phys. Condens. Matter. 2009, 21, 25507–25512.
(44) Yen, S. K.; Koh, L. L.; Huynh, H. V.; Hor, T. S. A. Pd(II) complexes with mixed benzothiazolin-2-ylidene and phosphine ligands and their catalytic activities toward C–C coupling reactions. Dalton Trans. 2008, 5, 699706.
(45) Huynh, H. V.; Han, Y.; Ho, J. H. H.; Tan, G. K. Palladium(II) complexes of a sterically bulky, benzannulated N-heterocyclic carbene with unusual intramolecular C−H···π and Ccarbene···Br interactions and their catalytic activities. Organometallics 2006, 25, 32673274.