A Convenient in Situ Preparation of Trimethylsilyl Iodide

Abstract

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