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N -Heterocyclic Carbene Catalyzed Cross Dehydrogenative Coupling of Aldehydes with Methanol: Combined Use of Eosin Y and Hexachloroethane

Cross dehydrogenative coupling of aldehydes with methanol was investigated under the organocatalytic conditions based on the cooperation between N-heterocyclic carbene and eosin Y·Na as an organophotocatalyst. The combined use of eosin Y·Na and C2Cl6 was the effective method for the oxidative esterification of various aldehydes, because the oxidation steps are promoted by two pathways associated with the activated photocatalyst and C2Cl6. In contrast, the combined use of eosin Y·Na and BrCCl3 was effective only for the oxidative esterification of simple cinnamaldehyde derivatives, in which BrCCl3 promoted the oxidation as a brominating reagent toward radical intermediates.