Diethyl phosphorocyanidate (DEPC) has been extensively utilized as a versatile reagent for cyanation under mild and non-aqueous reaction conditions. This article describes a new method for the synthesis of cyanophosphates by reaction of DEPC with various kinds of carbonyl compounds in the presence of lithium cyanide, and its application in organic synthesis is devided into four items : 1) synthesis of α, β-unsaturated nitriles and arylacetonitriles from aryl ketones
via cyanophosphates, 2) synthesis of 3-aryl-4-hydroxybenzonitriles from
p-benzoquinone cyanophosphates with aromatic and heteroaromatic compounds, 3) boron trifluoride etherate catalyzed allylic rearrangement of enone cyanophosphates and its application to β-cyanoenones, 4) 2-cyanoindole-3-acetonitriles from 3-indolecarbaldehydes
via cyanophosphates and its application to carbazole derivatives by cycloaddition with activated alkynes.
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