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M[TPP]Cl (M = Fe or Mn)-Catalyzed Oxidative Amination of Phenols by Primary and Secondary Anilines.

ABSTRACT: Iron- and manganese-catalyzed para-selective oxidative amination of (4-R)phenols by primary and secondary anilines was developed. Depending on the identity of the R group, the products of this efficient reaction are either benzoquinone anils (C-N coupling) that are produced via a sequential oxidative amination/dehydrogenation (R = H), oxidative amination/elimination (R = OMe) steps, or N,O-biaryl compounds (C-C coupling) that are formed when R = alkyl through an oxidative amination/[3,3]-sigmatropic rearrangement (quinamine rearrangement) process.

SUBMITTER: Vershinin V

PROVIDER: S-EPMC7467820 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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M[TPP]Cl (M = Fe or Mn)-Catalyzed Oxidative Amination of Phenols by Primary and Secondary Anilines.

Vershinin Vlada V Pappo Doron D

Organic letters 20200212 5

Iron- and manganese-catalyzed para-selective oxidative amination of (4-R)phenols by primary and secondary anilines was developed. Depending on the identity of the R group, the products of this efficient reaction are either benzoquinone anils (C-N coupling) that are produced via a sequential oxidative amination/dehydrogenation (R = H), oxidative amination/elimination (R = OMe) steps, or N,O-biaryl compounds (C-C coupling) that are formed when R = alkyl through an oxidative am ...[more]

PMID: 32049535

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