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Pure Appl. Chem., 1994, Vol. 66, No. 7, pp. 1527-1534

Catalytic C-H/olefin coupling

S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, Asayuki Kamatani, M. Sonoda and N. Chatani

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  • McKeown Bradley A., Gonzalez Hector Emanuel, Michaelos Thoe, Gunnoe T. Brent, Cundari Thomas R., Crabtree Robert H., Sabat Michal: Control of Olefin Hydroarylation Catalysis via a Sterically and Electronically Flexible Platinum(II) Catalyst Scaffold. Organometallics 2013, 32, 3903. <>
  • Arockiam Percia Beatrice, Bruneau Christian, Dixneuf Pierre H.: Ruthenium(II)-Catalyzed C–H Bond Activation and Functionalization. Chem. Rev. 2012, 112, 5879. <>
  • Fischmeister Cedric, Doucet Henri: Greener solvents for ruthenium and palladium-catalysed aromatic C–H bond functionalisation. Green Chem 2011, 13, 741. <>
  • Li Wenbo, Arockiam Percia B., Fischmeister Cedric, Bruneau Christian, Dixneuf Pierre H.: C–H bond functionalisation with [RuH(codyl)2]BF4 catalyst precursor. Green Chem 2011, 13, 2315. <>
  • Yang Luo, Correia Camille A., Li Chao-Jun: Rhodium-catalyzed C–H activation and conjugate addition under mild conditions. Biomol Chem 2011, 9, 7176. <>
  • MURAI S., KAKIUCHI F., SEKINE S., TANAKA Y., KAMATANI A., SONODA M., CHATANI N.: ChemInform Abstract: Catalytic C-H/Olefin Coupling. ChemInform 2010, 25, no. <>
  • Kakiuchi Fumitoshi, Kochi Takuya, Mizushima Eiichiro, Murai Shinji: Room-Temperature Regioselective C−H/Olefin Coupling of Aromatic Ketones Using an Activated Ruthenium Catalyst with a Carbonyl Ligand and Structural Elucidation of Key Intermediates. J Am Chem Soc 2010, 132, 17741. <>
  • Ishikawa Atsushi, Nakao Yoshihide, Sato Hirofumi, Sakaki Shigeyoshi: Pd(ii)-promoted direct cross-coupling reaction of arenes via highly regioselective aromatic C–H activation: a theoretical study. Dalton Trans 2010, 39, 3279. <>
  • Arockiam Percia, Poirier Valentin, Fischmeister Cédric, Bruneau Christian, Dixneuf Pierre H.: Diethyl carbonate as a solvent for ruthenium catalysed C–H bond functionalisation. Green Chem 2009, 11, 1871. <>
  • Lee John P., Jimenez-Halla J. Oscar C., Cundari Thomas R., Gunnoe T. Brent: Reactivity of TpRu(L)(NCMe)R (L=CO, PMe3; R=Me, Ph) systems with isonitriles: Experimental and computational studies toward the intra- and intermolecular hydroarylation of isonitriles. J Organomet Chem 2007, 692, 2175. <>
  • Omae Iwao: Three types of reactions with intramolecular five-membered ring compounds in organic synthesis. J Organomet Chem 2007, 692, 2608. <>
  • Bandini Marco, Emer Enrico, Tommasi Simona, Umani-Ronchi Achille: Innovative Catalytic Protocols for the Ring-Closing Friedel–Crafts-Type Alkylation and Alkenylation of Arenes. Eur J Org Chem 2006, 2006, 3527. <>
  • Jazzar Rodolphe F.R., Varrone Maurizio, Burrows Andrew D., Macgregor Stuart A., Mahon Mary F., Whittlesey Michael K.: Synthesis and isomerisation of two metallated N,O-complexes of ruthenium: Models for the Murai reaction. Inorg Chim Ada 2006, 359, 815. <>
  • Baik Chul, Han Won-Sik, Kang Youngjin, Kang Sang Ook, Ko Jaejung: Synthesis and photophysical properties of luminescent platinum(II) complexes with terdentate polypyridine ligands: [Pt(bpqb)X] and [Pt(tbbpqpy)X](PF6) (bpqb-H=1,3-bis(4′-phenyl-2′-quinolinyl) benzene; tbbpqpy=4-tert-butyl-1,3-bis(4′-phenyl-2′-quinolinyl) pyridine; X=Cl, CCC6H5, CCC6H4NMe2, CCC6H4NO2). J Organomet Chem 2006, 691, 5900. <>
  • Imhof W., Göbel A., Schweda L., Dönnecke D., Halbauer K.: The variation of coordination modes of aromatic imines in iron carbonyl complexes: Is there a correlation between bond lengths in organometallic model compounds and the reactivity of the ligands in catalytic C–C bond formation reactions?. J Organomet Chem 2005, 690, 3886. <>
  • Imhof Wolfgang, Göbel Angela, Schweda Linda, Görls Helmar: Synthesis and characterization of chiral iron carbonyl complexes from imine ligands with carbohydrates and amino acids as substituents. J Polyhedron 2005, 24, 3082. <>
  • Omae Iwao: Intramolecular five-membered ring compounds and their applications. Coord Chem Rev - 2004, 248, 995. <>
  • Guari Yannick, Castellanos Aida, Sabo-Etienne Sylviane, Chaudret Bruno: RuH2(H2)2(PCy3)2: a room temperature catalyst for the Murai reaction. J Mol Catal A Chem 2004, 212, 77. <>
  • Wohnrath K, Garcia J.R, Nart F.C, Batista A.A, Oliveira O.N: Electrochemical characterization of Langmuir–Blodgett films from the ruthenium complex mer-[RuCl3(dppb)(4-Mepy)]. This Solid Films 2002, 402, 272. <>
  • Cho Chan Sik, Kim Bok Tae, Lee Myung Jin, Kim Tae-Jeong, Shim Sang Chul: Ruthenium-Catalyzed Regioselectiveα-Alkylation of Ketones: The First Alkyl-Group Transfer from Trialkylamines to theα-C Atom of Ketones. Angew Chem 2001, 113, 984. <<984::AID-ANGE984>3.0.CO;2-P>
  • Echavarren Antonio M., Martín-Matute Belén, Mateo Cristina, Cárdenas Diego J.: Intramolecular C−H Activation by Alkylpalladium(II) Complexes: Insights into the Mechanism of the Palladium-Catalyzed Arylation Reaction. Chem Eur J 2001, 7, 2341. <<2341::AID-CHEM23410>3.0.CO;2-S>
  • Cho Chan Sik, Kim Bok Tae, Lee Myung Jin, Kim Tae-Jeong, Shim Sang Chul: Ruthenium-Catalyzed Regioselectiveα-Alkylation of Ketones: The First Alkyl-Group Transfer from Trialkylamines to theα-C Atom of Ketones. Angew Chem Int Ed 2001, 40, 958. <<958::AID-ANIE958>3.0.CO;2-4>
  • Du Hongguang, Liu Qun, Shi Shujian, Zhang Shiwei: Catalytic addition of ferrocenyl ketones to olefins with the aid of Ru(H)2(CO)(PPh3)3. J Organomet Chem 2001, 627, 127. <>
  • Berger Daniel, Göbel Angela, Imhof Wolfgang: Regioselective CC bond formation between ethylene and α-naphthylcarbaldimines catalyzed by Ru3(Co)12: NMR spectroscopic investigations on the proceeding of the reaction. Journal of Molecular Catalysis A 2001, 165, 37. <>
  • Oi Shuichi, Fukita Susumu, Hirata Naoki, Watanuki Noboru, Miyano Sotaro, Inoue Yoshio: Ruthenium Complex-Catalyzed Direct Ortho Arylation and Alkenylation of 2-Arylpyridines with Organic Halides. Org Lett 2001, 3, 2579. <>
  • Lei Ming, Feng Wenlin, Du Hongguang, Xu Zhenfeng: Theoretical investigation on regioselectivity of aromatic ketones in the addition with olefin catalyzed by RuH2(CO)(PPh3)3 . SCI CHINA SER B 2000, 43, 412. <>
  • Guari Yannick, Sabo-Etienne Sylviane, Chaudret Bruno: Catalytic Formation of Carbon–Carbon Bonds by Activation of Carbon–Hydrogen Bonds. Eur J Inorg Chem 1999, 1999, 1047. <<1047::AID-EJIC1047>3.0.CO;2-B>
  • Dyker Gerald: Übergangsmetall-katalysierte Kupplungsreaktionen unter C-H-Aktivierung. Angew Chem 1999, 111, 1808. <<1808::AID-ANGE1808>3.0.CO;2-V>
  • Herrmann Wolfgang A, Böhm Volker P.W, Reisinger Claus-Peter: Application of palladacycles in Heck type reactions. J Organomet Chem 1999, 576, 23. <>
  • Kakiuchi Fumitoshi, Sonoda Motohiro, Tsujimoto Takuya, Chatani Naoto, Murai Shinji: The Ruthenium-Catalyzed Addition of C-H Bonds in Aromatic Nitriles to Olefins. Chem Lett 1999, 1083. <>
  • Catalytic C-H Bond Activation-Asymmetric Olefin Coupling Reaction:The First Example of Asymmetric Fujiwara-Moritani Reaction Catalyzed by Chiral Palladium(II) Complexes. Chem Lett 1999, 55. <>
  • Harris Paul W.R., Woodgate Paul D.: Ruthenium-catalysed ortho alkylation of hydroxyacetophenones; the functionalisation of ring C aromatic diterpenoids. J Organomet Chem 1997, 530, 211. <>
  • Sonoda Motohiro, Kakiuchi Fumitoshi, Chatani Naoto, Murai Shinji: Ruthenium-Catalyzed Addition of Carbon-Hydrogen Bonds in Aromatic Ketones to Olefins. The Effect of Various Substituents at the Aromatic Ring. Bull Chem Soc Jpn 1997, 70, 3117. <>
  • Wang Guohong, Guo Hongjie, Weber William P.: Ruthenium-catalyzed regioselective step-growth copolymerization of 3′,4′-methylenedioxyacetophenone and α,ω-dienes. J Organomet Chem 1996, 521, 351. <>
  • Sonoda Motohiro, Kakiuchi Fumitoshi, Kamatani Asayuki, Chatani Naoto, Murai Shinji: Ruthenium-Catalyzed Addition of Aromatic Esters at the ortho C-H Bonds to Olefins. Chem Lett 1996, 109. <>
  • Sonoda Motohiro, Kakiuchi Fumitoshi, Chatani Naoto, Murai Shinji: Directing effect of functional groups in ruthenium-catalyzed addition of substituted acetophonones to an olefin. J Organomet Chem 1995, 504, 151. <>
  • Kakiuchi Fumitoshi, Sekine Shinya, Tanaka Yasuo, Kamatani Asayuki, Sonoda Motohiro, Chatani Naoto, Murai Shinji: Catalytic Addition of Aromatic Carbon-Hydrogen Bonds to Olefins with the Aid of Ruthenium Complexes. Bull Chem Soc Jpn 1995, 68, 62. <>
  • Kakiuchi Fumitoshi, Tanaka Yasuo, Sato Taisuke, Chatani Naoto, Murai Shinji: Catalytic Addition of Olefinic C-H Bonds to Olefins. Chem Lett 1995, 679. <>