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Communication | Regular issue | Vol 78, No. 11, 2009, pp.2735-2739
Published online, 10th September, 2009
DOI: 10.3987/COM-09-11799
Chemistry of Heteroaryltriphenylphosphonium Iodides: Preparation from Iodoheteroaromatics and Elimination of the Phosphonium Iodide Group Using Basic Solvents

Akihiro Sato, Osamu Sugimoto,* and Ken-ichi Tanji*

*Laboratory of Organic Chemistry, School of Food and Nutritional Sciences, University of Shizuoka, 52-1 Yada, Shizuoka 422-8526, Japan

Abstract

α- and γ-Iodoheteroaromatics were found to react with triphenylphosphine to give heteroaromatictriphenylphosphonium iodides in excellent yields. β-Iodoheteroaromatics, which are less reactive with triphenylphosphine compared to α- or γ-compounds, were converted into the corresponding phosphonium iodides using palladium catalysts. Treatment of heteroaryltriphenylphosphonium iodides resulted in the elimination of the phosphonium iodide group using basic solvents such as aqueous sodium hydroxide or ethanol - triethylamine.