A Single-Step Synthesis of Enynes: Pd-Catalyzed Arylalkynylation of Aryl Iodides, Internal Alkynes, and Alkynylsilanes

…, R Komatsu, N Uchida, R Ikeda, T Konakahara

Index: Sakai, Norio; Komatsu, Ryosuke; Uchida, Naoki; Ikeda, Reiko; Konakahara, Takeo Organic Letters, 2010 , vol. 12, # 6 p. 1300 - 1303

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Citation Number: 31

Abstract

First, when the reaction of 4-iodotoluene, diphenylacetylene (3 equiv), and 1-phenyl-2-trimethylsilylacetylene (1.5 equiv) was conducted in dimethylacetamide (DMA) at 100 °C in the presence of 2 mol % of Pd(OAc) 2 and 3 equiv of K 2 CO 3 as a model reaction, the 1,1,2-trisubstituted enyne derivative 1 was obtained in 42% yield along with the Sonogashira product 2 in 16% yield (run 1 in Table 1).(17) The geometric structure of 1 was determined from NOE and H−H COSY ...