Improved Solubility of Hypervalent Iodine-Benzyne Precursors: Synthesis and Reaction of (Phenyl)[2-(trimethylsilyl)phenyl]iodonium Salts Bearing Long Alkyl Chains

Abstract

Synthesis of new long-chained hypervalent iodine-benzyne precursors, (4-dodecylphenyl)[2-(trimethylsilyl)phenyl]iodonium triflate and the tetradecyl derivative, is described. The benzyne precursors dissolve even in organic solvents of low polarity such as diethyl ether, THF, cyclopentyl methyl ether, benzene, and toluene. The trapping reactions with furan and tetraphenylcyclopentadienone in the above solvent give the benzyne adducts in high yields without any loss of high reactivity of hypervalent iodine-benzyne precursors.

Key words

hypervalent iodine - benzyne - cycloaddition - high solubility - less polar solvent

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