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

Vlada Vershinin | Zendy; Doron Pappo | Zendy

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

Author(s) -

Vlada Vershinin,

Doron Pappo

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c00296

Subject(s) - chemistry , amination , primary (astronomy) , catalysis , phenols , oxidative phosphorylation , manganese , medicinal chemistry , organic chemistry , combinatorial chemistry , biochemistry , physics , astronomy

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.

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