Phosphine-Free Palladium-Catalyzed Decarboxylative Coupling of Alkynylcarboxylic Acids
mixture was washed with brine and water, and then extract-
ed with dichloromethane. The solvent was removed under
reduced pressure. And, mixture was then purified by silica
gel column chromatography using ethyl acetate/hexane as
eluent to give the desired product 2 as a yellow oil; yield:
1.144 g (3.68 mmol, 92%).
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Complex 3: A single-necked 25-mL round-bottom flask
was charged with the ligand
LiOH·H2O (0.084 g, 2.0 mmol) and 10 mL tetradydrofuran.
Pd(OAc)2 (0.202 g, 0.9 mmol) was added to the stirred solu-
2 (0.311 g, 1.0 mmol),
ACHTUNGTRENNUNG
tion at room temperature. After stirring the solution for
24 h at room temperature, a yellow-coloured solution was
obtained. The solvent was removed under reduced pressure
and the residue was washed with water and then with dieth-
yl ether. The resulting solid was dried under high vacuum to
obtain the pure complex 3; yield: 0.321 g (0.774 mmol,
86%).
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General Procedure for Decarboxylative Coupling
The reaction vessel was charged with aryl or heteroaryl
halide (0.5 mmol), alkynylcarboxylic acid (0.45 mmol),
Cs2CO3 (1 mmol), and the catalyst 3 (0.5 mol%) in N,N-di-
methylformamide (2 mL). The reaction mixture was heated
at 1408C in air and the progress of the reaction was moni-
tored by TLC. At the end of the reaction, the reaction mix-
ture was diluted with water (20 mL) and then extracted with
EtOAc (2ꢄ20 mL). The combined organic layers were
washed with brine (10 mL) and then dried over anhydrous
Na2SO4. After removal of the solvent, the crude product
was purified by flash chromatography over silica gel using
ethyl acetate/hexane as an eluent to afford the pure cou-
pling product.
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Acknowledgements
P.V.R. thanks CSIR, New Delhi for the award of Junior Re-
search Fellowship, P.S. thanks RMIT-IICT Joint Research
Centre for financial support.
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