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Aerobic Catalyzed Oxidative Cross-Coupling of N,N-Disubstituted Anilines and Aminonaphthalenes with Phenols and Naphthols.

ABSTRACT: The cross-coupling of N,N-dialkyl aniline and aminonaphthalenes with phenols and naphthols using a Cr-salen catalyst under aerobic conditions was developed. Notably, air serves as an effective oxidant affording products in high selectivity. Initial mechanistic studies suggest an outer-sphere oxidation of the aniline/aminonaphthalene partner, followed by nucleophilic attack of the phenol/naphthol. Single products were observed in most cases, whereas mixtures of C-C and C-O coupled products arose from reactions involving aminonapthalene and sterically unencumbered phenols.

SUBMITTER: Paniak TJ

PROVIDER: S-EPMC7060808 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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Aerobic Catalyzed Oxidative Cross-Coupling of N,N-Disubstituted Anilines and Aminonaphthalenes with Phenols and Naphthols.

Paniak Thomas J TJ Kozlowski Marisa C MC

Organic letters 20200212 5

The cross-coupling of N,N-dialkyl aniline and aminonaphthalenes with phenols and naphthols using a Cr-salen catalyst under aerobic conditions was developed. Notably, air serves as an effective oxidant affording products in high selectivity. Initial mechanistic studies suggest an outer-sphere oxidation of the aniline/aminonaphthalene partner, followed by nucleophilic attack of the phenol/naphthol. Single products were observed in most cases, whereas mixtures of C-C and C-O coupled p ...[more]

PMID: 32049541

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