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Photoarylation of Pyridines Using Aryldiazonium Salts and Visible Light: An EDA Approach.
Bartolomeu, Aloisio de A; Silva, Rodrigo C; Brocksom, Timothy J; Noël, Timothy; de Oliveira, Kleber T.
Afiliação
  • Bartolomeu AA; Departamento de Química , Universidade Federal de São Carlos , São Carlos , São Paulo 13565-905 , Brazil.
  • Silva RC; Department of Chemical Engineering and Chemistry, Sustainable Process Engineering, Micro Flow Chemistry & Synthetic Methodology , Eindhoven University of Technology , De Rondom 70 (Helix, STO 1.37) , 5612 AP Eindhoven , The Netherlands.
  • Brocksom TJ; Departamento de Química , Universidade Federal de São Carlos , São Carlos , São Paulo 13565-905 , Brazil.
  • Noël T; Departamento de Química , Universidade Federal de São Carlos , São Carlos , São Paulo 13565-905 , Brazil.
  • de Oliveira KT; Department of Chemical Engineering and Chemistry, Sustainable Process Engineering, Micro Flow Chemistry & Synthetic Methodology , Eindhoven University of Technology , De Rondom 70 (Helix, STO 1.37) , 5612 AP Eindhoven , The Netherlands.
J Org Chem ; 84(16): 10459-10471, 2019 Aug 16.
Article em En | MEDLINE | ID: mdl-31322352
A metal-free methodology for the photoarylation of pyridines, in water, is described giving 2 and 4-arylated-pyridines in yields up to 96%. The scope of the aryldiazonium salts is presented showing important results depending on the nature and position of the substituent group in the diazonium salt, that is, electron-donating or electron-withdrawing in the ortho, meta, or para positions. Further heteroaromatics were also successfully photoarylated. Mechanistic studies and comparison between our methodology and similar metal-catalyzed procedures are presented, suggesting the occurrence of a visible-light EDA complex which generates the aryl radical with no need for an additional photocatalyst.

Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2019 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2019 Tipo de documento: Article