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Synthesis of symmetrical diarylalkyne from palladium-catalyzed decarboxylative couplings of propiolic acid and aryl bromides under water

✍ Scribed by Kyungho Park; Goun Bae; Ahbyeol Park; Yong Kim; Jaehoon Choe; Kwang Ho Song; Sunwoo Lee


Publisher
Elsevier Science
Year
2011
Tongue
French
Weight
775 KB
Volume
52
Category
Article
ISSN
0040-4039

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✦ Synopsis


Symmetric diarylalkynes were obtained from the decarboxylative coupling reactions of aryl bromides and propiolic acid in water solvent condition. In the presence of phase transfer surfactant C 18 H 37 N(CH 3 ) 3 Cl, the catalytic system of both Pd(PPh 3 ) 2 Cl 2 /dppb and Pd(TPPMS) 2 Cl 2 /TPPMS afforded the desired coupled products in good yields.


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The experiments in Table 2 were carried out on a 1.00-mmol scale in 20-mL septum-capped vessels. The products were purified by column chromatography (SiO 2 , hexane/ethyl acetate gradient) after aqueous workup.