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Pure Appl. Chem., 2006, Vol. 78, No. 2, pp. 351-361

http://dx.doi.org/10.1351/pac200678020351

Palladium-catalyzed ring-forming reactions: Methods and applications

Mark Lautens, Dino Alberico, Cyril Bressy, Yuan-Qing Fang, Brian Mariampillai and Thorsten Wilhelm

Davenport Laboratories, Chemistry Department, University of Toronto, Toronto, Ontario M5S 3H6, Canada

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  • Prakash Praveen, Jijy Eliyan, Preethanuj Preethalayam, Pihko Petri M., Sarath Chand Sarngadharan, Radhakrishnan Kokkuvayil V.: Palladium-Catalyzed Skeletal Rearrangement of Spirotricyclic Olefins: A Facile One-Pot Strategy for the Synthesis of a Novel Motif with Cyclopentene Fused to Benzofuran and Pyrazolidine. Chem. Eur. J. 2013, 19, 10473. <http://dx.doi.org/10.1002/chem.201301475>
  • Yamada Takumasa, Yoshimura Fumihiko, Tanino Keiji: Synthesis of 2-cyano-1,4-cycloheptadiene derivatives via divinylcyclopropane rearrangement and alkylation of novel cycloheptadienyl anion species. Tetrahedron Letters 2013, 54, 522. <http://dx.doi.org/10.1016/j.tetlet.2012.11.070>
  • Yadav Ashok K., Verbeeck Stefan, Hostyn Steven, Franck Philippe, Sergeyev Sergey, Maes Bert U. W.: “Base Effect” in the Auto-Tandem Palladium-Catalyzed Synthesis of Amino-Substituted 1-Methyl-1H-α-carbolines. Org. Lett. 2013, 15, 1060. <http://dx.doi.org/10.1021/ol400064r>
  • Cheng Ming, Yan Jianwei, Hu Feng, Chen Hong, Hu Youhong: Palladium-catalyzed cascade reactions of 3-iodochromones with aryl iodides and norbornadiene leading to annulated xanthones. Chem. Sci. 2013, 4, 526. <http://dx.doi.org/10.1039/c2sc21335d>
  • Xie Hujun, Zhang Hong, Lin Zhenyang: DFT studies on the mechanisms of palladium-catalyzed intramolecular arylation of a silyl C(sp3)–H bond. New J. Chem. 2013, 37, 2856. <http://dx.doi.org/10.1039/c3nj00531c>
  • Jafarpour Farnaz, Jalalimanesh Nafiseh: Palladium/norbornene catalysis: a versatile aryl C–H hydroxyalkylation, alkyl cinnamate formation. Tetrahedron 2012, 68, 10286. <http://dx.doi.org/10.1016/j.tet.2012.10.013>
  • Cox Jason R., Kang Hyun A, Igarashi Takeshi, Swager Timothy M.: Norbornadiene End-Capping of Cross-Coupling Polymerizations: A Facile Route to Triblock Polymers. ACS Macro Lett 2012, 1, 334. <http://dx.doi.org/10.1021/mz200205k>
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  • Chernyak Dmitri, Chernyak Natalia, Gevorgyan Vladimir: Efficient and General Synthesis of 3-Aminoindolines and 3-Aminoindoles via Copper-Catalyzed Three-Component Coupling Reaction. Adv Synth Catal 2010, 352, 961. <http://dx.doi.org/10.1002/adsc.201000015>
  • Ca' Nicola Della, Motti Elena, Mega Antonio, Catellani Marta: One-Pot Palladium-Catalyzed Synthesis of Selectively Substituted Phenanthridines by Sequential Aryl-Aryl and Heck Couplings, Aza-Michael and Retro-Mannich Reactions. Adv Synth Catal 2010, 352, 1451. <http://dx.doi.org/10.1002/adsc.201000114>
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  • Ackermann Lutz, Vicente Rubén, Kapdi Anant R.: Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by CH Bond Cleavage. Angew Chem Int Ed 2009, 48, 9792. <http://dx.doi.org/10.1002/anie.200902996>
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  • Bellina Fabio, Rossi Renzo: Recent advances in the synthesis of (hetero)aryl-substituted heteroarenes via transition metal-catalysed direct (hetero)arylation of heteroarene C–H bonds with aryl halides or pseudohalides, diaryliodonium salts, and potassium aryltrifluoroborates. Tetrahedron 2009, 65, 10269. <http://dx.doi.org/10.1016/j.tet.2009.10.015>
  • Ca' Nicola Della, Sassi Giovanni, Catellani Marta: A Direct Palladium-Catalyzed Route to Selectively Substituted Carbazoles through Sequential CC and CN Bond Formation: Synthesis of Carbazomycin A. Adv Synth Catal 2008, 350, 2179. <http://dx.doi.org/10.1002/adsc.200800421>
  • Cariou Kevin, Ronan Baptiste, Mignani Serge, Fensterbank Louis, Malacria Max: From PtCl2- and Acid-Catalyzed to Uncatalyzed Cycloisomerization of 2-Propargyl Anilines: Access to Functionalized Indoles. Angew Chem 2007, 119, 1913. <http://dx.doi.org/10.1002/ange.200604026>
  • Cariou Kevin, Ronan Baptiste, Mignani Serge, Fensterbank Louis, Malacria Max: From PtCl2- and Acid-Catalyzed to Uncatalyzed Cycloisomerization of 2-Propargyl Anilines: Access to Functionalized Indoles. Angew Chem Int Ed 2007, 46, 1881. <http://dx.doi.org/10.1002/anie.200604026>
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  • Koranne Priti S., Tsujihara Tetsuya, Arai Midori A., Bajracharya Gan B., Suzuki Takeyuki, Onitsuka Kiyotaka, Sasai Hiroaki: Design and synthesis of chiral hybrid spiro (isoxazole–isoxazoline) ligands. Tet Asymm 2007, 18, 919. <http://dx.doi.org/10.1016/j.tetasy.2007.04.010>
  • Lautens Mark, Alberico Dino, Bressy Cyril, Fang Yuan-Qing, Mariampillai Brian, Wilhelm Thorsten: Palladium-Catalyzed Ring-Forming Reactions: Methods and Applications. ChemInform 2006, 37. <http://dx.doi.org/10.1002/chin.200631255>