A Convenientin SituPreparation of Trimethylsilyl Iodide

The ability of trimethylsilyl iodide (1) to effect a variety of useful synthetic transformations has been amply demonstrated. Thus, in the presence of 1, the following conversions are reported to occur efficiently and under mild conditions: hydrolysis of ethers1, carboxylate2 and phosphonate3 esters, carbamates4, acetals and ketals5; deoxygenation of sulfoxides6; formation of iodomethyl methyl ether from methylal7; formation of iodides from alcohols8; decarboxylation of β-ketoesters and gem-diesters9 and formation and subsequent reactions of aldehyde iodohydrin trimethylsilyl ethers derived from aldehydes.10 Despite the versatility and ready availability of 1 11, routine application in organic synthesis is limited by its marked instability toward hydrolysis. This has prompted several groups to devise suitable