Practical synthesis of aryl-2-methyl-3-butyn-2-ols from aryl bromides via conventional and decarboxylative copper-free Sonogashira coupling reactions

A Caporale, S Tartaggia, A Castellin…

Index: Caporale, Andrea; Tartaggia, Stefano; Castellin, Andrea; De Lucchi, Ottorino Beilstein Journal of Organic Chemistry, 2014 , vol. 10, p. 384 - 393

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Citation Number: 12

Abstract

Abstract Two efficient protocols for the palladium-catalyzed synthesis of aryl-2-methyl-3- butyn-2-ols from aryl bromides in the absence of copper were developed. A simple catalytic system consisting of Pd (OAc) 2 and P (p-tol) 3 using DBU as the base and THF as the solvent was found to be highly effective for the coupling reaction of 2-methyl-3-butyn-2-ol (4) with a wide range of aryl bromides in good to excellent yields. Analogously, the synthesis ...