Synthesis of Nitrogen‐Heterocycles Based on
            <scp>N</scp>
            ‐Heterocyclic Carbene Organocatalysis

Miyabe, Hideto

doi:10.1002/9781119757153.ch4

More Synthetic Approaches to Nonaromatic Nitrogen Heterocycles 2022

DOI: 10.1002/9781119757153.ch4

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Synthesis of Nitrogen‐Heterocycles Based on N ‐Heterocyclic Carbene Organocatalysis

Hideto Miyabe

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

Yoshioka¹,

Takahashi²,

Kubo³

et al. 2022

Synthesis

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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.

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

Yoshioka¹,

Takahashi²,

Kubo³

et al. 2022

Synthesis

View full text Add to dashboard Cite

show abstract

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Synthesis of Nitrogen‐Heterocycles Based on N ‐Heterocyclic Carbene Organocatalysis

Cited by 1 publication

References 169 publications

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

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

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