Organoselenium compounds have attracted considerable interest as reagents and intermediates in organic synthesis.~1 Selenoesters, a class of useful intermediates in the synthesis of natural compounds,~2 are commonly prepared by the reaction of acyl halides with selenols,~2,3 or by the alkylation of the selenolate ion.~4 Recently, other methods from arylselenotrimethyl-silane~5 and diselenides~6-8 have also been reported. However, most of these preparations are limited to alkyl esters, or involve difficult removal of by-products such as diaryl diselenides, harsh reaction conditions, laborious manipulation, low yields, or in some cases, reagents are not readily available. Herein, we report a one-pot, two-step synthesis of selenoesters (3) from alkynyl aryl selenides (1), which are treated succes sively with p-toluenesulfonic acid~9 and water. The present method has the advantage of ready avail-ability of starting materials, mild reaction condition, convenient manipulation and good (70-80) yields.
展开▼
