Synthesis of alpha,beta-Alkynyl Esters and Unsymmetrical Maleate Esters Catalyzed by Pd/C; An Efficient Phosphine-Free Catalytic System for Oxidative Alkoxycarbonylation of Terminal Alkynes

Pd/C-catalyzed oxidative alkoxycarbonylation of terminal alkynes using alcohols in the presence of tetrabutylammonium iodide under CO/O-2 (5:1 atm) has been investigated. The desired alpha,beta-alkynyl esters and unsymmetrical maleate esters are formed in good to excellent yields under different rea...

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Bibliographic Details
Published inSynlett Vol. 24; no. 8; pp. 981 - 986
Main Authors Gadge, Sandip T., Bhanage, Bhalchandra M.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 16.05.2013
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
heterogeneous catalysis
alkynes
2-ALKYNOATES
alcohols
FACILE SYNTHESIS
CARBON-MONOXIDE
SONOGASHIRA COUPLING REACTIONS
palladium
ARYL
AMINOCARBONYLATION
carbonylation
CYCLIZATION
MOLECULAR-OXYGEN
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Summary:Pd/C-catalyzed oxidative alkoxycarbonylation of terminal alkynes using alcohols in the presence of tetrabutylammonium iodide under CO/O-2 (5:1 atm) has been investigated. The desired alpha,beta-alkynyl esters and unsymmetrical maleate esters are formed in good to excellent yields under different reaction conditions. The present protocol eliminates the use of phosphine ligands and has straightforward catalyst recovery. The catalyst was recycled up to six times without significant loss of catalytic activity.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0032-1316896