A fast and direct iodide-catalyzed oxidative 2-selenylation of tryptophan

A metal-free 2-selenylation of tryptophan derivatives is reported, where the use of iodide as the catalyst and oxone as the oxidant is key to obtain high yields. Various functional groups within the di-seleny and the indole ring are tolerated, and no racemization is generally observed. We have developed a novel methodology for the synthesis of valuable 2-selenylated tryptophans from diselenides under the catalysis of iodide.