Tetrahedron

Palladium-catalyzed reactions of aryl iodides with trimethylsilylacetylenes and disubstituted alkynes: the synthesis of diarylacetylenes and triarylethylenes

MJ Wu, LM Wei, CF Lin, SP Leou, LL Wei

Index: Wu, Ming-Jung; Wei, Li-Mei; Lin, Chi-Fong; Leou, Shiow-Piaw; Wei, Li-Lan Tetrahedron, 2001 , vol. 57, # 37 p. 7839 - 7844

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Citation Number: 51

Abstract

Treatment of 2.5 equiv. of aryl iodide with trimethylsilylacetylene in the presence of 3equiv. of sodium methoxide and 5mol% of Pd (PPh3) 4 under refluxing methanol for 6h gave diarylacetylene in good chemical yields. When the catalyst was replaced by Pd (dba) 2 and 5equiv. of aryl iodide were added under the same reaction conditions, triarylethylenes were obtained in 70–85% yields. Only the sterically hindered o-methoxyiodobenzene and 2- ...