Reduction of Aromatic and Aliphatic Esters Using the Reducing Systems MoO2(acac)2 or V(O)(OiPr)3 in Combination with 1,1,3,3-Tetramethyldisiloxane

被引:38
作者
Pehlivan, Leyla [1 ]
Metay, Estelle [1 ]
Laval, Stephane [1 ]
Dayoub, Wissam [1 ]
Delbrayelle, Dominique [2 ]
Mignani, Gerard [3 ]
Lemaire, Marc [1 ]
机构
[1] Univ Lyon 1, Lab Catalyse & Synth Organ, ICBMS, CNRS,UMR 5246, F-69622 Villeurbanne, France
[2] Minakem SAS, F-59310 Beuvry La Foret, France
[3] Rhodia, Lyon Res Ctr, F-69192 St Fons, France
关键词
Synthetic methods; Reduction; Esters; Siloxanes; Molybdenum; Vana-dium; TITANOCENE-CATALYZED REDUCTION; CARBOXYLIC ESTERS; SELECTIVE REDUCTION; CHEMOSELECTIVE REDUCTION; EFFICIENT SYSTEM; ALCOHOLS; HYDROSILYLATION; LACTONES; ACIDS; POLYMETHYLHYDROSILOXANE;
D O I
10.1002/ejoc.201101016
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient reduction of aromatic and aliphatic esters with 1,1,3,3-tetramethyldisiloxane in combination with [MoO2(acac)2] or [V(O)(OiPr)3] is reported. In the former system, the presence of triphenylphosphane oxide allows high conversion and good isolated yield to be reached. For the latter system, no ligand is necessary to obtain the corresponding alcohols with similar results.
引用
收藏
页码:7400 / 7406
页数:7
相关论文
共 57 条
[1]  
Addis, 2011, ANGEW CHEM, V123, P6128
[2]   Selective Reduction of Carboxylic Acid Derivatives by Catalytic Hydrosilylation [J].
Addis, Daniele ;
Das, Shoubhik ;
Junge, Kathrin ;
Beller, Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (27) :6004-6011
[3]  
[Anonymous], 1991, REDUCTIONS ALUMINO B
[4]   TITANOCENE-CATALYZED REDUCTION OF ESTERS USING POLYMETHYLHYDROSILOXANE AS THE STOICHIOMETRIC REDUCTANT [J].
BARR, KJ ;
BERK, SC ;
BUCHWALD, SL .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) :4323-4326
[5]   A CATALYTIC METHOD FOR THE REDUCTION OF ESTERS TO ALCOHOLS [J].
BERK, SC ;
KREUTZER, KA ;
BUCHWALD, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (13) :5093-5095
[6]   AN AIR-STABLE CATALYST SYSTEM FOR THE CONVERSION OF ESTERS TO ALCOHOLS (VOL 57, PG 3751, 1992) [J].
BERK, SC ;
BUCHWALD, SL .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (11) :3221-3221
[7]   A catalytic method for the reduction of secondary and tertiary phosphine oxides [J].
Berthod, Mikael ;
Favre-Reguillon, Alain ;
Mohamad, Jahjah ;
Mignani, Gerard ;
Docherty, Gordon ;
Lemaire, Marc .
SYNLETT, 2007, (10) :1545-1548
[8]  
BOYER J, 1981, SYNTHESIS-STUTTGART, P558
[9]  
BREEDEN SW, 1994, SYNLETT, P833
[10]   SELECTIVE REDUCTIONS .30. EFFECT OF CATION AND SOLVENT ON THE REACTIVITY OF SALINE BOROHYDRIDES FOR REDUCTION OF CARBOXYLIC ESTERS - IMPROVED PROCEDURES FOR THE CONVERSION OF ESTERS TO ALCOHOLS BY METAL BOROHYDRIDES [J].
BROWN, HC ;
NARASIMHAN, S ;
CHOI, YM .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (24) :4702-4708