シリルテルリドを用いるラジカルカップリング反応

概要

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Silyltellurides react with carbonyl compounds and imines to generate α-silyloxy and α-silylaminoradicals, respectively. The radicals thus generated react with isonitriles and alkynes in a tellurium-group transfer manner to give the corresponding α-silyloxyimidoyltellurides, α-silyloxyvinyltellurides, and α-silylaminoimidoyltellurides, respectively. The coupling reaction proceeds under mild thermal and neutral conditions with the use of nearly an equivalent of each substrate. While the α-silyloxy and α-silylaminoradicals are deactivated by the tellurium-group transfer reaction to give α-silyloxytellrides and α-silylaminotellrides, respectively, they reversibly regenerate the same radical species under the reaction conditions. Therefore, all the starting substrates are eventually converted to the products. The carbon-tellurium bond in the products can be used for further synthetic transformations under radical and ionic conditions. Therefore, the coupling reaction and subsequent transformation provides a new synthetic method for combinatorial synthesis of synthetically important organic building blocks, such as α-alkoxy carbonyl compounds, α-amino acids, and allyl alcohols. Therefore, silyltellurides-mediated reaction opens a new possibility for the radical-mediated carbon-carbon bond formation involving carbon-hetero multiple bonds.
社団法人有機合成化学協会の論文
2003-08-01