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, 25422546.
(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, 23592365.
(3) Hopkinson, M. N.; Richter, C.; Schedler, M.; Glorius, F. An overview of N-heterocyclic carbenes. Nature 2014, 510, 485496.
(4) Lazreg, F.; Nahra, F.; Cazin, C. S. J. Copper-NHC complexes in catalysis. Coord. Chem. Rev. 2015, 293, 4879.
(5) Nelson, D. J.; Nolan, S. P. Quantifying and understanding the electronic properties of N-heterocyclic carbenes. Chem. Soc. Rev. 2013, 42, 67236753.
(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, 15181525.
(7) Valentine, D. H.; Hillhouse, J. H. Electron-rich phosphines in organic synthesis II. Catalytic applications. Synthesis 2003, 16, 24372460.
(8) Christmann, U.; Vilar, R. Monoligated palladium species as catalysts in cross‐coupling reactions. Angew Chem. Int. Ed. 2005, 44, 366374.
(9) Lee, M. T.; Hu, C. H. Density functional study of N-heterocyclic and diamino carbene complexes: comparison with phosphines. Organometallics 2004, 23, 976983.
(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, c7c9.
(11) Crabtree, R. H. NHC ligands versus cyclopentadienyls and phosphines as spectator ligands in organometallic catalysis. J. Organomet. Chem. 2005, 690 54515457.
(12) Gaillard, S.; Renaud, J. L. When phosphorus and NHC (N-heterocyclic carbene) meet each other. Dalton Trans. 2013, 42, 72557270.
(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, 601614.
(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, 12901309.
(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, 14401449.
(18) Poyatos, M.; Mata, J. A.; Peris, E. Complexes with poly(N-heterocyclic carbene) ligands: structural features and catalytic applications. Chem. Rev. 2009, 109, 36773707.
(19) Diez-Gonzalez, S.; Marion, N.; Nolan, S. P. N-heterocyclic carbenes in late transition metal catalysis. Chem. Rev. 2009, 109, 36123676.
(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, 755764.
(21) Süssner, M.; Plenio, H. π-Face donor properties of N-heterocyclic carbenes. Chem. Commun. 2005, 43, 54175419.
(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 54075413.
(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, 405417.
(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, 1093210937.
(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, 229236.
(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, 51055113.
(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, 325334.
(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, 5971.
(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, 463472.
(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, 617618, 616628.
(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, 57925800.
(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, 1443450.
(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, 887897.
(35) Sheldrick, G. M. SHELXT-integrated space-group and crystal-structure determination. Acta Cryst. 2015, A71, 38.
(36) Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Cryst. 2015, C71, 38.
(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, 339341.
(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, 159916004.
(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, 32453248.
(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, 4356.
(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, 3845.
(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, 699706.
(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, 32673274.
|