Radical Arylation of Anilines and Pyrroles via Aryldiazotates

Journal article


Publication Details

Author(s): Hofmann J, Gans E, Clark T, Heinrich M
Journal: Chemistry - A European Journal
Publisher: WILEY-V C H VERLAG GMBH
Publication year: 2017
Volume: 23
Journal issue: 40
Pages range: 9647-9656
ISSN: 0947-6539
eISSN: 1521-3765


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.


FAU Authors / FAU Editors

Clark, Timothy apl. Prof. Dr.
Computer-Chemie-Centrum
Gans, Eva
Lehrstuhl für Pharmazeutische Chemie
Heinrich, Markus Prof. Dr.
Professur für Pharmazeutische Chemie
Hofmann, Josefa
Lehrstuhl für Pharmazeutische Chemie


How to cite

APA:
Hofmann, J., Gans, E., Clark, T., & Heinrich, M. (2017). Radical Arylation of Anilines and Pyrroles via Aryldiazotates. Chemistry - A European Journal, 23(40), 9647-9656. https://dx.doi.org/10.1002/chem.201701429

MLA:
Hofmann, Josefa, et al. "Radical Arylation of Anilines and Pyrroles via Aryldiazotates." Chemistry - A European Journal 23.40 (2017): 9647-9656.

BibTeX: 

Last updated on 2019-13-01 at 07:09