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- Title
Radical Arylation of Anilines and Pyrroles via Aryldiazotates.
- Authors
Hofmann, Josefa; Gans, Eva; Clark, Timothy; Heinrich, Markus R.
- Abstract
The radical arylation of anilines and pyrroles can be achieved under transition-metal- and catalyst-free conditions by using aryldiazotates in strongly alkaline aqueous solutions. The aryldiazotates act as protected diazonium ions, which do not undergo azo coupling with electron-rich aromatic substrates, but can still serve as an aryl radical source at slightly elevated temperatures. Based on an improved preparation of aryldiazotates in aqueous solution, homolytic aromatic substitutions of anilines and pyrroles were conducted with good overall yields and high regioselectivity. Moreover, DFT calculations provided further mechanistic insights.
- Subjects
ANILINE; ARYLATION; PYRROLES; DIAZOATES; AQUEOUS solutions
- Publication
Chemistry - A European Journal, 2017, Vol 23, Issue 40, p9647
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201701429