We thank the Fonds der Chemischen Industrie for support (stipend to E. K.).
Regioselective Threefold Aromatic Substitution of Benzoic Acid Derivatives by Dearomatization, Regioselective Functionalization, and Rearomatization†
Article first published online: 26 MAR 2013
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 52, Issue 18, pages 4933–4936, April 26, 2013
How to Cite
Koch, E. and Studer, A. (2013), Regioselective Threefold Aromatic Substitution of Benzoic Acid Derivatives by Dearomatization, Regioselective Functionalization, and Rearomatization . Angew. Chem. Int. Ed., 52: 4933–4936. doi: 10.1002/anie.201300259
- Issue published online: 21 APR 2013
- Article first published online: 26 MAR 2013
- Manuscript Received: 11 JAN 2013
- Fonds der Chemischen Industrie
- aromatic substitution;
- CC coupling;
- synthetic methods
Ipso, meta, and para: Benzoic acid derivatives can be highly regioselectively substituted at the ipso, meta, and para positions. The reaction sequence comprises an alkylative Birch reduction, a 4-alkylation, a palladium-catalyzed γ-arylation, and an oxidative rearomatization (see scheme). All the reactions are robust and experimentally easy to conduct.