Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals.

نویسندگان

  • L Candish
  • M Freitag
  • T Gensch
  • F Glorius
چکیده

Herein we present the first example of aryl radical formation via the visible light-mediated decarboxylation of aryl carboxylic acids using photoredox catalysis. This method constitutes a mild protocol for the decarboxylation of cheap and abundant aryl carboxylic acids and tolerates both electron-rich substrates and those lacking ortho-substitution. The in situ formation of an acyl hypobromite is proposed to prevent unproductive hydrogen atom abstraction and trapping of the intermediate aroyloxy radical, enabling mild decarboxylation.

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منابع مشابه

Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6sc05533h Click here for additional data file.

1. General information S2 2. Synthesis of carboxylic acids S3 3. Stoichiometric experiments with benzoyl hypobromite II S4 4. Optimization and control reactions S8 5. Oxidant screen S9 6. General procedure for the visible light-promoted aryl decarboxylation S9 7. Scope of the visible light-promoted decarboxylation/radical trapping S10 8. Mechanistic studies S19 a) Stern-Volmer luminescence quen...

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عنوان ژورنال:
  • Chemical science

دوره 8 5  شماره 

صفحات  -

تاریخ انتشار 2017