Synthesis of Arylacetylenes by the Sodium Hydride Catalyzed Cleavage of 4-Aryl-2-methyl-3-butyn-2-ols

SJ Havens, PM Hergenrother

Index: Havens, Stephen J.; Hergenrother, Paul M. Journal of Organic Chemistry, 1985 , vol. 50, # 10 p. 1763 - 1765

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Citation Number: 102

Abstract

Ethynyltrimethylsilane provides an excellent vehicle for the introduction of an acetylene group to an aromatic nucleus. Reaction of aryl halides (bromide or iodide) with ethynyltrimethylsilane in a secondary or tertiary amine solvent containing a small amount of palladium catalyst has given quantitative yields of (trimethy1silyl) ethynylaryls. 1* 2npb The trimethylsilyl protecting group is easily removed by treatment with dilute potassium ...