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

Eito Yoshioka; Hiroki Takahashi; Akane Kubo; Miki Ohno; Fuuka Watanabe; Rino Shiono; Yuuki Miyazaki; Hideto Miyabe

doi:10.1055/a-1918-4406

Synthesis, Table of Contents

Synthesis 2022; 54(24): 5520-5528
DOI: 10.1055/a-1918-4406

paper

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

Eito Yoshioka

,

Hiroki Takahashi

,

Akane Kubo

,

Miki Ohno

,

Fuuka Watanabe

,

Rino Shiono

,

Yuuki Miyazaki

,

Hideto Miyabe∗

Abstract

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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

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