, MANUSCRIPT
, 5-di-tert-butylbenzyl)-3-(2,4,6-trimethylbenzyl)benzimidazole-2-ylidene](pyridine)palladium(II), (2e) Yield: 0.26 g, 74%; mp: 259-260 o C. 1 H NMR, pp.1-21
, 30 (s, 9H, NCH2C6H2(CH3)3-2,4,6)13 (s, 2H, NCH2C6H3(C(CH3)3)2-3,5), pp.15-17
, CH3)3-2,4,6, NCH2C6H3(C(CH3)3)2-3,5 and NC5H5) 13 C NMR (100 MHz, CDCl3): 21.0 and 21, NCH2C6H2(CH3)3-2, pp.31-36
, NCH2C6H3(C(CH3)3)-3,5)) IR (cm -1 ) v(CN): 1410; Anal
, 6-tetramethylbenzyl)benzimidazole-2-ylidene](pyridine)palladium(II), (2f) Yield: 0.29 g, 77%, o C. 1 H NMR (400 MHz, CDCl3): 1.21 (s, 18H, NCH2C6H3(C(CH3)3), pp.267-2682
, ), 2.20 and 2.21 (s, 12H, NCH2C6H(CH3)4-2,3, pp.1416-1418
, NCH2C6H3(C(CH3)3)2-3,5 and NC5H5) 13 C NMR (100 MHz, CDCl3): 15.6 and 19, m, 13H, NC6H4N, NCH2C6H(CH3)4-2,3NCH2C6H(CH3)4-2,3, pp.5-7
, )3)-3,5)), Pd-Ccarbene). IR (cm -1 ) v(CN): 1416; Anal. Calcd. for C38H47Br2N3Pd: C, pp.56-77
, 5.83; N, 5.17. Found: C, 56.24; H, 5
, 3-(4-tert-butylbenzyl)benzimidazole-2-ylidene](pyridine)palladium(II), (2g) Yield: 0.32 g, 87%; mp: 264-265 o C. 1 H NMR (400 MHz), CDCl3): 1.23 (s, 27H, NCH2C6H3(C(CH3)3)2-3, pp.2-6
, )3)2-3, NCH2C6H4(C(CH3)3-4) and NC5H5). 13 C NMR, pp.98-129
, C(CH3)3)2-3,5), pp.31-36
, C(CH3)3)2-3,5) 13 C NMR (75 MHz, CDCl3): 111(C(CH3)3-4) and NC5H5) IR (cm -1 ) v(CN): 1414; Anal, 7 (NC6H4N, NCH2C6H3(C(CH3)3)2-3, pp.2-6
, Yield: 0.23 g, 67%; Yield: 0.21 g, 72%; mp: 206-207 o C. 1 H NMR (400 MHz, CDCl3): 1.22 (s, 36H, NCH2C6H3(C(CH3)3)2-3,5), 17 (s, 4H, NCH2C6H3(C(CH3)3), pp.3-13
, 3 (NCH2C6H3(C(CH3)3)2-3,5) (Pd-Ccarbene) IR (cm -1 ) v(CN): 1411; Anal, NC6H4N, NCH2C6H3(C(CH3)3)2-3,5 and NC5H5
, N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Synthetic Tools N-Heterocyclic Carbenes in Transition Metal Catalysis and Organocatalysis, RSC, vol.32, 2010.
N-Heterocyclic Carbenes in Transition Metal Catalysis, Topics in Organometallic Chemistry, 2007. ,
DOI : 10.1007/978-3-540-36930-1
, N-Heterocyclic Carbenes: Effective Tools for Organometallic Synthesis, 2014.
N-Heterocyclic Carbenes in Late Transition Metal Catalysis, Chemical Reviews, vol.109, issue.8, pp.3612-3676, 2009. ,
DOI : 10.1021/cr900074m
Organocatalysis by N-Heterocyclic Carbenes, Chemical Reviews, vol.107, issue.12, pp.5606-5655, 2007. ,
DOI : 10.1021/cr068372z
N-Heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: a perfect union, Chemical Society Reviews, vol.14, issue.618, pp.5151-5169, 2011. ,
DOI : 10.1002/chem.200701621
An overview of N-heterocyclic carbenes, Nature, vol.5, issue.7506, pp.485-496, 2014. ,
DOI : 10.1038/nchem.1710
N-Heterocyclic Carbenes: A New Concept in Organometallic Catalysis, Angewandte Chemie International Edition, vol.40, issue.618, pp.1290-1309, 2002. ,
DOI : 10.1002/1521-3773(20011217)40:24<4544::AID-ANIE4544>3.0.CO;2-N
Recent homogeneous catalytic applications of chelate and pincer N-heterocyclic carbenes, Coordination Chemistry Reviews, vol.248, issue.21-24, pp.2239-2246, 2004. ,
DOI : 10.1016/j.ccr.2004.04.014
Electronic Nature of N-Heterocyclic Carbene Ligands:??? Effect on the Suzuki Reaction, Organic Letters, vol.7, issue.10, pp.1991-1994, 2005. ,
DOI : 10.1021/ol050471w
-Heterocyclic Carbenes as Effective Catalysts in Olefin Metathesis, Organometallics, vol.36, issue.11, pp.2153-2166, 2017. ,
DOI : 10.1021/acs.organomet.7b00211
NHC ligands versus cyclopentadienyls and phosphines as spectator ligands in organometallic catalysis, Journal of Organometallic Chemistry, vol.690, issue.24-25, pp.5451-5457, 2005. ,
DOI : 10.1016/j.jorganchem.2005.07.099
N-heterocyclic carbene transition metal complexes for catalysis in aqueous media, Chemical Society Reviews, vol.13, issue.21, pp.7032-7060, 2012. ,
DOI : 10.1039/c0gc00807a
N-Heterocyclic carbene metal complexes in medicinal chemistry, Dalton Trans., vol.38, issue.10, pp.3269-3284, 2013. ,
DOI : 10.3109/03639045.2011.589853
Metal N-heterocyclic carbene complexes as potential antitumor metallodrugs, Chem. Soc. Rev., vol.6, issue.2, pp.755-773, 2013. ,
DOI : 10.1002/cmdc.201100308
, Inorg. Chem, vol.23, pp.414-427, 2005.
, Eur. J. Med. Chem, pp.90-82, 2015.
N -heterocyclic carbenes (NHC) with 1,2,4-oxadiazole-substituents related to natural products: Synthesis, structure and potential antitumor activity of some corresponding gold(I) and silver(I) complexes, European Journal of Medicinal Chemistry, vol.101, pp.431-441, 2015. ,
DOI : 10.1016/j.ejmech.2015.06.053
Novel benzimidazol-2-ylidene carbene precursors and their silver(I) complexes: Potential antimicrobial agents, Bioorganic & Medicinal Chemistry, vol.24, issue.16, pp.3649-3656, 2016. ,
DOI : 10.1016/j.bmc.2016.06.004
, N-Heterocyclic Carbenes in Synthesis, 2006.
(N-Heterocyclic Carbene)-Palladate Complexes in Anionic Mizoroki???Heck Coupling Cycles: A Combined Experimental and Computational Study, Organometallics, vol.34, issue.11, pp.2463-2470, 2015. ,
DOI : 10.1021/om5012038
Reactions of the 21st Century: Two Decades of Innovative Catalyst Design for Palladium-Catalyzed Cross-Couplings, Organometallics, vol.34, issue.23, pp.5497-5508, 2015. ,
DOI : 10.1021/acs.organomet.5b00567
, Chem. Commun, vol.27, pp.3190-3192, 2008.
A new stereospecific cross-coupling by the palladium-catalyzed reaction of 1-alkenylboranes with 1-alkenyl or 1-alkynyl halides, Tetrahedron Letters, vol.20, issue.36, pp.3437-3440, 1979. ,
DOI : 10.1016/S0040-4039(01)95429-2
, Org. Chem. J. Org. Chem, vol.64, pp.3804-3805, 1999.
Cross-Coupling of Organic Halides with Alkenes: The Heck Reaction, Metal-catalyzed cross-coupling reactions, 2004. ,
DOI : 10.1002/9783527619535.ch5
, Negishi, Bull. Chem. Soc. Jpn. Org. Lett, vol.80, issue.7, pp.233-257, 2005.
Efficient Cross-Coupling Reactions of Aryl Chlorides and Bromides with Phenyl- or Vinyltrimethoxysilane Mediated by a Palladium/Imidazolium Chloride System, Organic Letters, vol.2, issue.14, pp.2053-2055, 2000. ,
DOI : 10.1021/ol005956t
Chelating N-heterocyclic carbene ligands in palladium-catalyzed heck-type reactions, Journal of Organometallic Chemistry, vol.557, issue.1, pp.93-96, 1998. ,
DOI : 10.1016/S0022-328X(97)00736-5
General and Efficient Catalytic Amination of Aryl Chlorides Using a Palladium/Bulky Nucleophilic Carbene System, Organic Letters, vol.1, issue.8, pp.1307-1309, 1999. ,
DOI : 10.1021/ol990987d
, Org. Lett. Chem. Commun, vol.66, issue.2, pp.7729-7737, 2000.
, Modern arylation methods, 2009.
Direct Arylation of Arene C???H Bonds by Cooperative Action of NHCarbene???Ruthenium(II) Catalyst and Carbonate via Proton Abstraction Mechanism, Journal of the American Chemical Society, vol.130, issue.4, pp.1156-1157, 2008. ,
DOI : 10.1021/ja710276x
, Chem. J. Coord. Chem. Pure Appl. Chem, vol.13, issue.62, pp.1942-1949, 2008.
An Overview of the Clinical Safety Profile of Atorvastatin (Lipitor), a New HMG-CoA Reductase Inhibitor, Archives of Internal Medicine, vol.158, issue.6, pp.577-584, 1998. ,
DOI : 10.1001/archinte.158.6.577
Norbinaltorphimine: Antagonist profile at ?? opioid receptors, European Journal of Pharmacology, vol.144, issue.3, pp.405-408, 1987. ,
DOI : 10.1016/0014-2999(87)90397-9
,
,
Molecular and Pharmacological Properties of a Potent and Selective Novel Nonsteroidal Progesterone Receptor Agonist Tanaproget, Journal of Biological Chemistry, vol.75, issue.31, pp.28468-28475, 2005. ,
DOI : 10.3109/00498258109045302
, Reviews in the Neurosciences, vol.19, pp.245-316, 2008.
, J. Org. Chem. Adv. Synth. Catal. ChemCatChem Angew. Chem. Int. Ed, vol.76, issue.356 2, pp.471-483, 2010.
, Heterocycles, pp.31-1951, 1990.
1173-1193; d), Aldrichimica Acta Chem. Soc. Rev. Synlett Tetrahedron Chem. Commun. J. Am. Chem. Soc. Angew. Chem. Int. Ed. Green Chem, vol.36, issue.13, pp.200-205, 2007. ,
-Heterocyclic carbene???palladium catalysts for the direct arylation of pyrrole derivatives with aryl chlorides, Beilstein Journal of Organic Chemistry, vol.9, pp.303-312, 2013. ,
DOI : 10.3762/bjoc.9.35
, Appl. Organomet. Chem, 2017.
, Chem. Eur. J, pp.12-4743, 2006.
, J. Appl. Cryst, pp.32-115, 1999.
, C71 (2015) 3-8. ACCEPTED MANUSCRIPT
, Table 1 Bond lengths Bond angles Pd1-C6 1.952(7) C6-Pd1-N1 177, ) Pd1-N1 2.087(6) C6-Pd1-Br1 89.1(2) Pd1-Br1 2.426(1) C6-Pd1-Br2) N1-Pd1-Br2 90, pp.1-1364