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

Abstract

Cross dehydrogenative coupling of aldehydes with methanol was investigated under 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 hexachloro­ethane (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 bromotrichloromethane (BrCCl₃) was effective only for the oxidative esterification of simple cinnamaldehyde derivatives, in which BrCCl₃ promotes the oxidation as a brominating reagent toward radical intermediates.

Key words

N-heterocyclic carbenes - photocatalysts - organocatalysis - cross dehydrogenative coupling - oxidation - radicals - aldehydes - esters

Publication History

Received: 01 July 2022

Accepted: 04 August 2022

Accepted Manuscript online:
04 August 2022

Article published online:
14 September 2022

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