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

[Image: see text] 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 s...

Descripción completa

Detalles Bibliográficos
Autores principales: Vershinin, Vlada, Pappo, Doron
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2020
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7467820/
https://www.ncbi.nlm.nih.gov/pubmed/32049535
http://dx.doi.org/10.1021/acs.orglett.0c00296
_version_ 1783578091105288192
author Vershinin, Vlada
Pappo, Doron
author_facet Vershinin, Vlada
Pappo, Doron
author_sort Vershinin, Vlada
collection PubMed
description [Image: see text] 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.
format Online
Article
Text
id pubmed-7467820
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-74678202020-09-03 M[TPP]Cl (M = Fe or Mn)-Catalyzed Oxidative Amination of Phenols by Primary and Secondary Anilines Vershinin, Vlada Pappo, Doron Org Lett [Image: see text] 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. American Chemical Society 2020-02-12 2020-03-06 /pmc/articles/PMC7467820/ /pubmed/32049535 http://dx.doi.org/10.1021/acs.orglett.0c00296 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Vershinin, Vlada
Pappo, Doron
M[TPP]Cl (M = Fe or Mn)-Catalyzed Oxidative Amination of Phenols by Primary and Secondary Anilines
title M[TPP]Cl (M = Fe or Mn)-Catalyzed Oxidative Amination of Phenols by Primary and Secondary Anilines
title_full M[TPP]Cl (M = Fe or Mn)-Catalyzed Oxidative Amination of Phenols by Primary and Secondary Anilines
title_fullStr M[TPP]Cl (M = Fe or Mn)-Catalyzed Oxidative Amination of Phenols by Primary and Secondary Anilines
title_full_unstemmed M[TPP]Cl (M = Fe or Mn)-Catalyzed Oxidative Amination of Phenols by Primary and Secondary Anilines
title_short M[TPP]Cl (M = Fe or Mn)-Catalyzed Oxidative Amination of Phenols by Primary and Secondary Anilines
title_sort m[tpp]cl (m = fe or mn)-catalyzed oxidative amination of phenols by primary and secondary anilines
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7467820/
https://www.ncbi.nlm.nih.gov/pubmed/32049535
http://dx.doi.org/10.1021/acs.orglett.0c00296
work_keys_str_mv AT vershininvlada mtppclmfeormncatalyzedoxidativeaminationofphenolsbyprimaryandsecondaryanilines
AT pappodoron mtppclmfeormncatalyzedoxidativeaminationofphenolsbyprimaryandsecondaryanilines

Ejemplares similares