Synthesis of 3-Substituted Tetrahydrofuran and 4-Substituted Tetrahydropyran Derivatives by Cyclization of Dicarboxylic Acids with InBr3/TMDS

被引：29
作者：
Pehlivan, Leyla [1 ]
Metay, Estelle [1 ]
Delbrayelle, Dominique [2 ]
Mignani, Gerard [3 ]
Lemaire, Marc [1 ]
机构：
[1] Univ Lyon 1, CNRS, UMR 5246, Lab Catalyse & Synth Organ,ICBMS, F-69622 Villeurbanne, France
[2] Minakem SAS, F-59310 Beuvry La Foret, France
[3] Rhodia, Lyon Res Ctr, F-69192 St Fons, France
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 25期
关键词：
Cyclization; Indium; Oxygen heterocycles; Carboxylic acids; Reduction; RADICAL CYCLIZATION; CYCLIC ETHERS; REDUCTION; SYSTEM;
D O I：
10.1002/ejoc.201200727
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient reduction followed by cyclization of diacid compounds with the InBr3/TMDS system is reported. This system allows the formation of five- and six-membered ring ethers substituted in the 3- or 4-position.
引用
收藏
页码：4689 / 4693
页数：5
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  • [21] A New Solvent-Free Reaction for the Preparation of Alkoxysilane from Cyclic Ethers, Alcohols, or Carbonyl Compounds
    Pehlivan, Leyla
    Metay, Estelle
    Boyron, Olivier
    Demonchaux, Patrice
    Mignani, Gerard
    Lemaire, Marc
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (24) : 4687 - 4692
  • [22] Alternative method for the reduction of aromatic nitro to amine using TMDS-iron catalyst system
    Pehlivan, Leyla
    Metay, Estelle
    Laval, Stephane
    Dayoub, Wissam
    Demonchaux, Patrice
    Mignani, Gerard
    Lemaire, Marc
    [J]. TETRAHEDRON, 2011, 67 (10) : 1971 - 1976
  • [23] Iron-catalyzed selective reduction of nitro compounds to amines
    Pehlivan, Leyla
    Metay, Estelle
    Laval, Stephane
    Dayoub, Wissam
    Demonchaux, Patrice
    Mignani, Gerard
    Lemaire, Marc
    [J]. TETRAHEDRON LETTERS, 2010, 51 (15) : 1939 - 1941
  • [24] A straightforward synthesis of unsymmetrical secondary phosphine boranes
    Petit, Christelle
    Favre-Reguillon, Alain
    Mignani, Gerard
    Lemaire, Marc
    [J]. GREEN CHEMISTRY, 2010, 12 (02) : 326 - 330
  • [25] Mechanistic Insight into the Reduction of Tertiary Phosphine Oxides by Ti(OiPr)4/TMDS
    Petit, Christelle
    Favre-Reguillon, Alain
    Albela, Belen
    Bonneviot, Laurent
    Mignani, Gerard
    Lemaire, Marc
    [J]. ORGANOMETALLICS, 2009, 28 (22) : 6379 - 6382
  • [26] A simple one-pot entry to cyclic ethers of varied ring sizes from diols via phosphonium ion induced iodination and base catalyzed Williamson etherification
    Roy, Biswajit Gopal
    Roy, Ashim
    Achari, Basudeb
    Mandal, Sukhendu B.
    [J]. TETRAHEDRON LETTERS, 2006, 47 (44) : 7783 - 7787
  • [27] Direct Reduction of Esters to Ethers with an Indium(III) Bromide/Triethylsilane Catalytic System
    Sakai, Norio
    Moriya, Toshimitsu
    Fujii, Kohji
    Konakahara, Takeo
    [J]. SYNTHESIS-STUTTGART, 2008, 21 (21): : 3533 - 3536
  • [28] Indium-Catalyzed Reductive Esterification of a Carboxylic Acid: Sequential Preparation of an Ester and Symmetrical Ether
    Sakai, Norio
    Usui, Yuta
    Ikeda, Reiko
    Konakahara, Takeo
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (18) : 3397 - 3401
  • [29] InBr3-Catalyzed Deoxygenation of Carboxylic Acids with a Hydrosilane: Reductive Conversion of Aliphatic or Aromatic Carboxylic Acids to Primary Alcohols or Diphenylmethanes
    Sakai, Norio
    Kawana, Keita
    Ikeda, Reiko
    Nakaike, Yumi
    Konakahara, Takeo
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (17) : 3178 - 3183
  • [30] Formation of cyclic ethers via the palladium-catalyzed cycloaddition of activated olefins with allylic carbonates having a hydroxy group at the terminus of the carbon chain
    Sekido, M
    Aoyagi, K
    Nakamura, H
    Kabuto, C
    Yamamoto, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (21) : 7142 - 7147
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