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Base directed palladium catalysed Heck arylation of acrolein diethyl acetal in water

Paper ID Volume ID Publish Year Pages File Format Full-Text
40174 45845 2014 9 PDF Available
Title
Base directed palladium catalysed Heck arylation of acrolein diethyl acetal in water
Abstract

•Heck arylation of acrolein diethylacetal to aldehydes or acids in water media.•Selectivity is controlled through the nature of the base.•Cinnamaldehydes are obtained in the presence of sodium acetate.•3-Arylpropionic acids are obtained in the presence of diisopropylamine.•The use of RAME-β-CD as mass transfer additive allowed increasing the reaction rate.

The selective Heck arylation of acrolein diethyl acetal catalysed by [Pd(NH3)4]Cl2 in the presence of RAME-β-CD in water as solvent is described. Depending on the base (i.e. NaOAc or HN(i-Pr)2) good to high selectivity's towards, respectively, the cinnamaldehydes 2 or the 3-arylpropionic esters 1 were achieved. The results support that depending on the base different palladium intermediate complexes are formed. Using NaOAc, {[ArPdX(H2O)2]} complex is preferentially generated giving the cinnamaldehyde 2. On the other hand, in the presence of HN(i-Pr)2, a L-type ligand, [ArPdX(HN(i-Pr)2(H2O)] or [ArPdX(HN(i-Pr)2(HN(i-Pr)2)] will be generated leading to the formation of the 3-arylpropionic ester 1. For the last, coordinated amine participates very probably to the formation of the esters through intramolecular syn β-H elimination.

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Keywords
Heck arylation; Water; Cyclodextrins; Palladium catalysts; Acrolein; Cinnamaldehyde; 3-Arylpropionic esters
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Base directed palladium catalysed Heck arylation of acrolein diethyl acetal in water
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Publisher
Database: Elsevier - ScienceDirect
Journal: Applied Catalysis A: General - Volume 469, 17 January 2014, Pages 250–258
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
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Price was $35.95
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