Abstract
An ultrasound irradiation–promoted Heck reaction catalyzed by ligand-free palladium acetate was described. The ultrasound-promoted Heck reaction was carried out under mild and environmentally friendly conditions, resulting in the corresponding products with good to excellent chemical yields (up to 96% yield) and high regioselectivities and stereoselectivities (E/Z > 99:1). Acrylamide and acrylic acid were used for the first time as substrates in the ultrasound-promoted Heck reaction. It was found that the reaction could be finished within 20 min.
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ACKNOWLEDGMENTS
We gratefully acknowledge financial support from the National Natural Science Foundation of China (No. 20772056 to Y.P.). This work was also partially supported by research funds from the Qing-Lan Program of Jiangsu Province, the Kua-Shi-Ji Program of the Education Ministry of China, and the Jiangsu 333 program (for Pan).
Notes
a Iodobenzene (5 mmol), acrylamide (6 mmol), base (7.5 mmol), Pd(OAc)2 (0.05 mmol), surfactant (0.5 mmol), and water (20 mL).
b Determined by 1H NMR. Only E-isomer was detected.
c Isolated yield.
a Aryl iodide (5 mmol), acrylamide (6 mmol), K2CO3 (7.5 mmol), Pd(OAc)2 (0.05 mmol), sodium dodecane-1-sulfonate (0.5 mmol), and water (20 mL) at 90 °C for 20 min.
b Determined by 1H NMR. Only E-isomer was detected.
c Isolated yields.
a Iodobenzene (5 mmol), olefin (6 mmol), K2CO3 (7.5 mmol), Pd(OAc)2 (0.05 mmol), sodium dodecane-1-sulfonate (0.5 mmol), and water (20 mL), at 90 °C for 20 min.
b Determined by 1H NMR. Only E-isomer was found.
c Isolated yields.