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Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 861-871

http://dx.doi.org/10.1351/pac200880050861

Ruthenium catalysts for selective nucleophilic allylic substitution

Christian Bruneau, Jean-Luc Renaud and Bernard Demerseman

UMR 6226, CNRS-Université de Rennes 1: Sciences Chimiques de Rennes, Catalyse et Organométalliques, Campus de Beaulieu-35042 Rennes Cedex, France

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  • Siddappa Ravi Kumara Guralamatta, Chang Chih-Wei, Chein Rong-Jie: From precursor to catalyst: the involvement of [Ru(η5-Cp∗)Cl2]2 in highly branch selective allylic etherification of cinnamyl chlorides. Tetrahedron Letters 2014, 55, 1031. <http://dx.doi.org/10.1016/j.tetlet.2013.12.074>
  • Kawatsura Motoi, Uchida Kenta, Terasaki Shou, Tsuji Hiroaki, Minakawa Maki, Itoh Toshiyuki: Ruthenium-Catalyzed Regio- and Enantioselective Allylic Amination of Racemic 1-Arylallyl Esters. Org. Lett. 2014, 16, 1470. <http://dx.doi.org/10.1021/ol5002768>
  • Zhang Xiao, Liu Wen-Bo, Wu Qing-Feng, You Shu-Li: Ruthenium-Catalyzed Intramolecular Allylic Dearomatization Reaction of Indole Derivatives. Org. Lett. 2013, 15, 3746. <http://dx.doi.org/10.1021/ol4016578>
  • Zhang Xiao, Yang Ze-Peng, Liu Chuan, You Shu-Li: Ru-catalyzed intermolecular dearomatization reaction of indoles with allylic alcohols. Chem. Sci. 2013, 4, 3239. <http://dx.doi.org/10.1039/c3sc51313k>
  • He Hu, Ye Ke-Yin, Wu Qing-Feng, Dai Li-Xin, You Shu-Li: Iridium-Catalyzed Asymmetric Allylic Etherification and Ring-Closing Metathesis Reaction for Enantioselective Synthesis of Chromene and 2,5-Dihydrobenzo[b]oxepine Derivatives. Synth Catal 2012, 354, 1084. <http://dx.doi.org/10.1002/adsc.201100809>
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  • Benedetto Elena, Keita Massaba, Tredwell Matthew, Hollingworth Charlotte, Brown John M., Gouverneur Véronique: Platinum-Catalyzed Substitution of Allylic Fluorides. Organomettalics 2012, 31, 1408. <http://dx.doi.org/10.1021/om201029m>
  • Garcı́a-Álvarez Rocío, Suárez Francisco J., Dı́ez Josefina, Crochet Pascale, Cadierno Victorio, Antiñolo Antonio, Fernández-Galán Rafael, Carrillo-Hermosilla Fernando: Ruthenium(II) Arene Complexes with Asymmetrical Guanidinate Ligands: Synthesis, Characterization, and Application in the Base-Free Catalytic Isomerization of Allylic Alcohols. Organometallics 2012, 31, 8301. <http://dx.doi.org/10.1021/om3009124>
  • Ahammed Sabir, Saha Amit, Ranu Brindaban C.: Ruthenium catalysed one-pot synthesis of S-allyl and cinnamyl dithiocarbamates using allyl and cinnamyl acetates in water. RSC Adv. 2012, 2, 6329. <http://dx.doi.org/10.1039/c2ra20856c>
  • Barile Fabio, Bassetti Mauro, D'Annibale Andrea, Gerometta Renzo, Palazzi Michele: Cross-Metathesis Reactions of Homoallyl Methyl Malonates with Sterically Hindered Allylic Esters. Eur J Org 2011, 2011, 6519. <http://dx.doi.org/10.1002/ejoc.201100916>
  • Zhang Ping, Le Hai, Kyne Robert E., Morken James P.: Enantioselective Construction of All-Carbon Quaternary Centers by Branch-Selective Pd-Catalyzed Allyl–Allyl Cross-Coupling. J Am Chem Soc 2011, 133, 9716. <http://dx.doi.org/10.1021/ja2039248>
  • Ye Ke-Yin, He Hu, Liu Wen-Bo, Dai Li-Xin, Helmchen Günter, You Shu-Li: Iridium-Catalyzed Allylic Vinylation and Asymmetric Allylic Amination Reactions with o-Aminostyrenes. S J Am Chem Soc 2011, 133, 19006. <http://dx.doi.org/10.1021/ja2092954>
  • Štambaský Jan, Kapras Vojtěch, Štefko Martin, Kysilka Ondřej, Hocek Michal, Malkov Andrei V., Kočovský Pavel: A Modular Approach to Aryl-C-ribonucleosides via the Allylic Substitution and Ring-Closing Metathesis Sequence. A Stereocontrolled Synthesis of All Four α-/β- and d-/l-C-Nucleoside Stereoisomers. J Org Chern 2011, 76, 7781. <http://dx.doi.org/10.1021/jo201110z>
  • Brancatelli Giovanna, Drommi Dario, Feminò Giusy, Saporita Maria, Bottari Giovanni, Faraone Felice: Basicity and bulkiness effects of 1,8-diaminonaphthalene, 8-aminoquinoline and their alkylated derivatives on the different efficiencies of η5-C5H5 and η5-C5Me5 ruthenium precatalysts in allylic etherification reactions. New J Chem 2010, 34, 2853. <http://dx.doi.org/10.1039/c0nj00338g>
  • Saporita Maria, Bottari Giovanni, Bruno Giuseppe, Drommi Dario, Faraone Felice: Regio- and enantioselectivity in the alkylation and etherification reactions of cinnamyl allylic derivatives catalyzed by [(η5-C5R5)Ru(N–N*)(NCCH3)]PF6 (R=H, Me) complexes containing N–N* bulky chiral ligands of different rigidity and flexibility. Journal of Molecular Catalysis A 2009, 309, 159. <http://dx.doi.org/10.1016/j.molcata.2009.05.011>
  • Bruneau Christian, Renaud Jean-Luc, Demerseman Bernard: ChemInform Abstract: Ruthenium Catalysts for Selective Nucleophilic Allylic Substitution. ChemInform 2008, 39. <http://dx.doi.org/10.1002/chin.200843253>
  • Linder David, Buron Frédéric, Constant Samuel, Lacour Jérôme: Enantioselective CpRu-Catalyzed Carroll Rearrangement - Ligand and Metal Source Importance. Eur J Org Chem 2008, 2008, 5778. <http://dx.doi.org/10.1002/ejoc.200800854>
  • Bouziane Asmae, Carboni Bertrand, Bruneau Christian, Carreaux François, Renaud Jean-Luc: Pentamethylcyclopentadienyl ruthenium: an efficient catalyst for the redox isomerization of functionalized allylic alcohols into carbonyl compounds. Tetrahedron 2008, 64, 11745. <http://dx.doi.org/10.1016/j.tet.2008.09.095>