Abstract:
There are relatively few basic type reactions that generate a new
carbon-carbon bond, although this is one of the most critical operations in
the synthesis of organic molecules. Vinylic derivatives are versatile
compounds in the synthetic chemistry and hence a method for their synthesis
has been explored. In view of the extensive natural occurrence and
biological importance of unsaturated ester a general method for the synthesis
of substituted acrylate through palladium-catalyzed reaction using arylhalide
and alkyl acrylate is reported.
R=CH3
R=CzHs
R=n-C4H9
CH=CHCOOR
X=H
X=p-CH30
X=p-CH3
X = o-NHCOCH3
X=p-Cl
X=p-NOz
X=p-COOH
X 18-28
(PPh3h PdCIz, DMF •
CHz=CH-COOR
Et3N, rt, 30 hrs 8-14
I
X
The coupling reaction was carried out by stirring a mixture of aryliodide
8-14 and alkylacrylate 15-17 in presence of bis (triphenylphosphene)
palladium (II) chloride as a catalyst and triethylamine as a base in
dimethylformamide (DMF) at room temperature. The condensed product
was purified by column chromatography to afford unsaturated ester 18-28.
The ester was subjected to hydrolysis to yield unsaturated carboxylic acid
29-31. The synthesized compounds were characterized based on analytical
data obtained from IR, UV, IHNMR 13CNMR and melting points.
