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22.2.3.1.1.2 Variation 2: With Sodium Hydrogen Selenide

DOI: 10.1055/sos-SD-022-00233

Wirth, T.Science of Synthesis, (200522184.

A more general synthesis of O-alkyl and O-aryl selenoates has been developed using sodium hydrogen selenide.[‌28‌] In this process, N,N-disubstituted amides 8 are treated with phosgene to generate N,N-dimethylimidoyl chlorides 9. The reaction of this salt with alcohols affords the N,N-dimethylimidoyl esters 10, which are then treated with sodium hydrogen selenide to give the corresponding selenoates 11 in moderate to good yields (Scheme 4). Even selenoformates 11 (R1=H) can be obtained by this procedure, but the products have to be isolated quickly because they decompose rapidly.

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