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Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 845-854

http://dx.doi.org/10.1351/pac200880050845

Reaction of alcohols and silyl ethers in the presence of an indium/silicon-based catalyst system: Deoxygenation and allyl substitution

Akio Baba, Makoto Yasuda, Yoshihiro Nishimoto, Takahiro Saito and Yoshiyuki Onishi

Department of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan

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  • Onishi Yoshiharu, Nishimoto Yoshihiro, Yasuda Makoto, Baba Akio: Indium Chloride Catalyzed Alkylative Rearrangement of Propargylic Acetates Using Alkyl Chlorides, Alcohols, and Acetates: Facile Synthesis of α-Alkyl-α,β-Unsaturated Carbonyl Compounds. Org. Lett. 2014, 16, 1176. <http://dx.doi.org/10.1021/ol500046e>
  • Wakabayashi Ryutaro, Kuroda Kazuyuki: Siloxane-Bond Formation Promoted by Lewis Acids: A Nonhydrolytic Sol-Gel Process and the Piers-Rubinsztajn Reaction. ChemPlusChem 2013, 78, 764. <http://dx.doi.org/10.1002/cplu.201300027>
  • Herrmann Josef M., König Burkhard: Reductive Deoxygenation of Alcohols: Catalytic Methods Beyond Barton-McCombie Deoxygenation. Eur. J. Org. Chem. 2013, 2013, 7017. <http://dx.doi.org/10.1002/ejoc.201300657>
  • Zhu Lizhi, Zhou Congshan, Yang Wei, He Shuzhong, Cheng Gui-Juan, Zhang Xinhao, Lee Chi-Sing: Formal Syntheses of (±)-Platensimycin and (±)-Platencin via a Dual-Mode Lewis Acid Induced Cascade Cyclization Approach. J. Org. Chem. 2013, 78, 7912. <http://dx.doi.org/10.1021/jo401105q>
  • Nishimoto Yoshihiro, Okita Aya, Yasuda Makoto, Baba Akio: Synthesis of a Wide Range of Thioethers by Indium Triiodide Catalyzed Direct Coupling between Alkyl Acetates and Thiosilanes. Z Org Lett 2012, 14, 1846. <http://dx.doi.org/10.1021/ol300450j>
  • Nishimoto Yoshihiro, Okita Aya, Yasuda Makoto, Baba Akio: Indium Tribromide Catalyzed Cross-Claisen Condensation between Carboxylic Acids and Ketene Silyl Acetals Using Alkoxyhydrosilanes. angew chemie 2011, 123, 8782. <http://dx.doi.org/10.1002/ange.201104140>
  • Nishimoto Yoshihiro, Okita Aya, Yasuda Makoto, Baba Akio: Indium Tribromide Catalyzed Cross-Claisen Condensation between Carboxylic Acids and Ketene Silyl Acetals Using Alkoxyhydrosilanes. Angew Chem Int E 2011, 50, 8623. <http://dx.doi.org/10.1002/anie.201104140>
  • Meyer Vera J., Niggemann Meike: Calcium-Catalyzed Direct Coupling of Alcohols with Organosilanes. Eur J Org Chem 2011, 2011, 3671. <http://dx.doi.org/10.1002/ejoc.201100231>
  • Xu Yan-li, Pan Ying-ming, Wu Qiang, Wang Heng-shan, Liu Pei-zhen: Regioselective Synthesis of 1,3,5-Substituted Benzenes via the InCl3/2-Iodophenol-Catalyzed Cyclotrimerization of Alkynes. J Org Chern 2011, 76, 8472. <http://dx.doi.org/10.1021/jo201010d>
  • Tsuchimoto Teruhisa: Development of New Catalytic Reactions Based on Activation of Hydrocarbon Functional Groups by Lewis Acids. J Syn Org Chem Jpn 2011, 69, 889. <http://dx.doi.org/10.5059/yukigoseikyokaishi.69.889>
  • Nishimoto Yoshihiro, Inamoto Yoshihiro, Saito Takahiro, Yasuda Makoto, Baba Akio: Indium Triiodide Catalyzed Direct Hydroallylation of Esters. Eur J Org Chem 2010, 2010, 3382. <http://dx.doi.org/10.1002/ejoc.201000475>
  • Ramesh Namakkal G., Nagaraj Paramathevar: Stereoselective synthesis of 2-C-methylene glycosides and disaccharides via direct allylic substitution of hydroxy group in benzylated glycals. Tetrahed 2010, 66, 599. <http://dx.doi.org/10.1016/j.tet.2009.11.082>
  • Nishimoto Yoshihiro, Onishi Yoshiharu, Yasuda Makoto, Baba Akio: ��-Alkylation of Carbonyl Compounds by Direct Addition of Alcohols to Enol Acetates. Angew Chem 2009, 121, 9295. <http://dx.doi.org/10.1002/ange.200904069>
  • Nishimoto Yoshihiro, Onishi Yoshiharu, Yasuda Makoto, Baba Akio: ��-Alkylation of Carbonyl Compounds by Direct Addition of Alcohols to Enol Acetates. Angew Chem Int Ed 2009, 48, 9131. <http://dx.doi.org/10.1002/anie.200904069>
  • Nagaraj Paramathevar, Ramesh Namakkal G.: Direct Ferrier rearrangement on unactivated glycals catalyzed by indium(III) chloride. Tetrahetron Lett 2009, 50, 3970. <http://dx.doi.org/10.1016/j.tetlet.2009.04.084>
  • Takikawa Hiroshi, Hikita Katsuyoshi, Suzuki Keisuke: Isoxazole-Assisted Direct Substitution of the Hydroxy Group in α-Ketols: Introduction of Angular Substituents in a Polycyclic System. Angew Chem 2008, 120, 10035. <http://dx.doi.org/10.1002/ange.200801577>
  • Takikawa Hiroshi, Hikita Katsuyoshi, Suzuki Keisuke: Isoxazole-Assisted Direct Substitution of the Hydroxy Group in α-Ketols: Introduction of Angular Substituents in a Polycyclic System. Angew Chem Int Ed 2008, 47, 9887. <http://dx.doi.org/10.1002/anie.200801577>
  • Baba Akio, Yasuda Makoto, Nishimoto Yoshihiro, Saito Takahiro, Onishi Yoshiyuki: ChemInform Abstract: Reactions of Alcohols and Silyl Ethers in the Presence of an Indium/Silicon-Based Catalyst System: Deoxygenation and Allyl Substitution. ChemInform 2008, 39. <http://dx.doi.org/10.1002/chin.200843255>