Alkynylphenyliodonium tosylates

A mixture of the appropriate diaryl ditelluride (1 mmol) and sodium borohydride (2.2 mmol) in DMF (10 luL) was stirred under an N2 atmosphere at 50-60°C until the solution was clear. The mixture was allowed to cool to room temperature, an appropriate alkynylphenyliodonium tosylate (2 mmol and DMF (10 mL)) was added and stirring was continued at 70-80°C under N2. The course of the reaction was followed by TLC. When the reaction was completed, the mixture was cooled, diluted with water (15 mL) and the product was extracted with petroleum ether (3x 10 mL). The combined extracts were washed with water, and dried with MgS04. After removal of the solvent, the residue was chromatographed on a column of silica gel using CH2CI2 as eluent to give the acetylenic teUuride. 

Alkynylphenyliodonium tosylates react with trialkyl phosphites in a formal Michaelis-Arbuzov reaction to give dialkyl 1-aIkynylphosphonates (Scheme 1.5). It seems plausible that the first step... 

Zhang, J.-L., and Chen, Z.-C., Hypervalent iodine in synthesis. Part 25. Alkynylphenyliodonium tosylates as alkynylating reagents. Direct conversion of alkynylphenyhodonium tosylates to dialkyl alkynylphosphonates with sodium dialkylphosphonates, Synth. Commun., 28, 175, 1998. 

A second type is the reaction of alkynylphenyliodonium tosylates with benzoate loaded ion exchange resin. Alkynyl benzoates (86) and phenyl iodide were the products which could result from ligand coupling on the intermediate alkynylphenyliodonium benzoates. However, isolation of these intermediates has not been possible. 1 6 (Scheme 5.8) The same reaction with diethyl phospHate led to the corresponding phosphate esters (87). 1 5,197... 

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