Hypervalent iodine reagents became a new hot topic in synthetic organic chemistry in the last decade. Due to electrophilic character, high reactivity, low toxicity, easy preparation and general stability the +3 oxidation state organic iodonium salts are widespread in arylation, alkenylation, alkynylation or alkylation reactions. In this work we improved the preparation of aryl(trifloxyvinyl)iodonium triflate salts1-3 and developed a practical synthesis to obtain aryl(vinyl)iodonium compounds with high efficiency. This one-pot transformation starts easily from acetylenes, commercially available (diacetoxyiodo)benzene (DIB) and trimethylsilyl triflate to prepare wide variety of aryl(trifloxyvinyl)iodonium salts in good yields. Our procedure allowed to synthesize 25 new highly reactive phenyl(trifloxyvinyl) iodonium triflate salts functionalized with alkyl, aralkyl, aryl and heteroaryl groups. Geometry of the C=C double bond in these compounds has been established by NOE-NMR experminets and X-ray crystallography.

Synthesis of highly substituted aryl(trifloxyvinyl)iodonium triflate salts

2019 Spring National Meeting

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