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Pure Appl. Chem., 2001, Vol. 73, No. 2, pp. 319-324

http://dx.doi.org/10.1351/pac200173020319

New developments in transition metal-catalyzed synthetic reactions via C-H bond activation

Yuzo Fujiwara* and Chengguo Jia

Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Hakozaki, Fukuoka 812-8581, JAPAN.

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  • Girard Simon A., Knauber Thomas, Li Chao-Jun: Dehydrierende Kreuzkupplungen von C sp 3-H-Bindungen: vielseitige Verfahren zur Bildung von C-C-Bindungen. Angew. Chem. 2014, 126, 76. <http://dx.doi.org/10.1002/ange.201304268>
  • Girard Simon A., Knauber Thomas, Li Chao-Jun: The Cross-Dehydrogenative Coupling of C sp 3H Bonds: A Versatile Strategy for CC Bond Formations. Angew. Chem. Int. Ed. 2014, 53, 74. <http://dx.doi.org/10.1002/anie.201304268>
  • Ryu Ilhyong, Tani Akihiro, Fukuyama Takahide, Ravelli Davide, Montanaro Sara, Fagnoni Maurizio: Efficient C–H/C–N and C–H/C–CO–N Conversion via Decatungstate-Photoinduced Alkylation of Diisopropyl Azodicarboxylate. Org. Lett. 2013, 15, 2554. <http://dx.doi.org/10.1021/ol401061v>
  • Wen Zhen-Kang, Xu Yun-He, Loh Teck-Peng: Palladium(ii)-catalyzed cross-coupling of simple alkenes with acrylates: a direct approach to 1,3-dienes through C–H activation. Chem. Sci. 2013, 4, 4520. <http://dx.doi.org/10.1039/c3sc52275j>
  • Chai Zhuo, Rainey Trevor J.: Pd(II)/Brønsted Acid Catalyzed Enantioselective Allylic C–H Activation for the Synthesis of Spirocyclic Rings. S J Am Chem Soc 2012, 134, 3615. <http://dx.doi.org/10.1021/ja2102407>
  • Li Zejiang, Zhang Yuexia, Liu Zhong-Quan: Pd-Catalyzed Olefination of Perfluoroarenes with Allyl Esters. Org Lett 2012, 14, 74. <http://dx.doi.org/10.1021/ol202859b>
  • Zhang Yuexia, Li Zejiang, Liu Zhong-Quan: Pd-Catalyzed Olefination of Furans and Thiophenes with Allyl Esters. Org Lett 2012, 14, 226. <http://dx.doi.org/10.1021/ol203013p>
  • Zhang Yuexia, Cui Zili, Li Zejiang, Liu Zhong-Quan: Pd(II)-Catalyzed Dehydrogenative Olefination of Vinylic C–H Bonds with Allylic Esters: General and Selective Access to Linear 1,3-Butadienes. Z Org Lett 2012, 14, 1838. <http://dx.doi.org/10.1021/ol300442w>
  • Ryu Ilhyong, Tani Akihiro, Fukuyama Takahide, Ravelli Davide, Fagnoni Maurizio, Albini Angelo: Atom-Economical Synthesis of Unsymmetrical Ketones through Photocatalyzed CH Activation of Alkanes and Coupling with CO and Electrophilic Alkenes. Angew Chem 2011, 123, 1909. <http://dx.doi.org/10.1002/ange.201004854>
  • Liu Yu, Li Dan, Park Cheol-Min: Stereoselective Synthesis of Highly Substituted Enamides by an Oxidative Heck Reaction. angew chemie 2011, 123, 7471. <http://dx.doi.org/10.1002/ange.201101550>
  • Ryu Ilhyong, Tani Akihiro, Fukuyama Takahide, Ravelli Davide, Fagnoni Maurizio, Albini Angelo: Atom-Economical Synthesis of Unsymmetrical Ketones through Photocatalyzed CH Activation of Alkanes and Coupling with CO and Electrophilic Alkenes. Angew Chem Int Ed 2011, 50, 1869. <http://dx.doi.org/10.1002/anie.201004854>
  • Liu Yu, Li Dan, Park Cheol-Min: Stereoselective Synthesis of Highly Substituted Enamides by an Oxidative Heck Reaction. Angewandte Chemie-Int Ed 2011, 50, 7333. <http://dx.doi.org/10.1002/anie.201101550>
  • Théveau Laure, Verrier Cécile, Lassalas Pierrik, Martin Thibaut, Dupas Georges, Querolle Olivier, Van Hijfte Luc, Marsais Francis, Hoarau Christophe: Mechanism Selection for Regiocontrol in Base-Assisted, Palladium-Catalysed Direct CH Coupling with Halides: First Approach for Oxazole- and Thiazole-4-Carboxylates. Chemistry A European Journal 2011, 17, 14450. <http://dx.doi.org/10.1002/chem.201101615>
  • Piotrowicz Michał, Zakrzewski Janusz, Makal Anna, Bąk Joanna, Malińska Maura, Woźniak Krzysztof: Aerobic Fujiwara–Moritani alkenylation and dienylation of ferrocene. j organometall chem 2011, 696, 3499. <http://dx.doi.org/10.1016/j.jorganchem.2011.07.029>
  • Roiban Gheorghe-Doru, Serrano Elena, Soler Tatiana, Aullón Gabriel, Grosu Ion, Cativiela Carlos, Martínez Manuel, Urriolabeitia Esteban P.: Regioselective Orthopalladation of (Z)-2-Aryl-4-Arylidene-5(4H)-Oxazolones: Scope, Kinetico-Mechanistic, and Density Functional Theory Studies of the C–H Bond Activation. Inorg. Chem. 2011, 50, 8132. <http://dx.doi.org/10.1021/ic200564d>
  • Cho Seung Hwan, Kim Ji Young, Kwak Jaesung, Chang Sukbok: Recent advances in the transition metal-catalyzed twofold oxidative C–H bond activation strategy for C–C and C–N bond formation. Chem Soc Rev 2011, 40, 5068. <http://dx.doi.org/10.1039/c1cs15082k>
  • Hsiao Chien-Chi, Lin Yi-Kuan, Liu Chia-Ju, Wu Tsun-Cheng, Wu Yao-Ting: Synthesis of Methylene-Bridge Polyarenes through Palladium-Catalyzed Activation of Benzylic Carbon-Hydrogen Bond. Adv Synth Catal 2010, 352, 3267. <http://dx.doi.org/10.1002/adsc.201000651>
  • Fujiwara Yuzo, Jia Chengguo: ChemInform Abstract: New Developments in Transition Metal Catalyzed Synthetic Reactions via C-H Bond Activation. ChemInform 2010, 32, no. <http://dx.doi.org/10.1002/chin.200142279>
  • Anastas Paul, Eghbali Nicolas: Green Chemistry: Principles and Practice. Chem Soc Rev 2010, 39, 301. <http://dx.doi.org/10.1039/b918763b>
  • Wu Junliang, Cui Xiuling, Chen Lianmei, Jiang Guojie, Wu Yangjie: Palladium-Catalyzed Alkenylation of Quinoline-N-oxides via C−H Activation under External-Oxidant-Free Conditions. J Am Chem Soc 2009, 131, 13888. <http://dx.doi.org/10.1021/ja902762a>
  • Verrier Cécile, Hoarau Christophe, Marsais Francis: Direct palladium-catalyzed alkenylation, benzylation and alkylation of ethyl oxazole-4-carboxylate with alkenyl-, benzyl- and alkyl halides. Org Biomol Chem 2009, 7, 647. <http://dx.doi.org/10.1039/b816374j>
  • Roiban Doru, Serrano Elena, Soler Tatiana, Grosu Ion, Cativiela Carlos, Urriolabeitia Esteban P.: Unexpected [2 + 2] C–C bond coupling due to photocycloaddition on orthopalladated (Z)-2-aryl-4-arylidene-5(4H)-oxazolones. Chem Commun 2009, 4681. <http://dx.doi.org/10.1039/b907647f>
  • Graham Todd W., Ong Christopher, Wei Pingrong, Stephan Douglas W.: Reactions of the titanium-carbide species CpTi(μ2-Me)(μ2-NPi-Pr3)(μ4-C)(AlMe2)3. J Organomet Chem 2007, 692, 4481. <http://dx.doi.org/10.1016/j.jorganchem.2007.03.011>