Journal of the American Chemical Society 2004-10-20

Radical deoxygenation of hydroxyl groups via phosphites.

Liming Zhang, Masato Koreeda

Index: J. Am. Chem. Soc. 126(41) , 13190-1, (2004)

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Abstract

A highly efficient, two-step sequence method for the deoxygenation of hydroxyl groups has been developed. The method involves the preparation of the 2-(2-iodophenyl)ethyl methyl phosphite derivative of an alcohol using methyl dichlorophosphite and 2-(2-iodophenyl)ethanol. Treatment of the phosphite intermediate with (n-Bu)3SnH/AIBN in refluxing benzene cleanly produces the deoxygenation product of the original alcohol.