Beyond Friedel and Crafts: Innate Alkylation of C−H Bonds in Arenes
- 3 June 2019
- journal article
- review article
- Published by Wiley in Angewandte Chemie
- Vol. 58 (23), 7558-7598
- https://doi.org/10.1002/anie.201806631
Abstract
Alkylated arenes are ubiquitous molecules and building blocks commonly utilized in most areas of science where there is a need for small organic molecules. Despite its apparent simplicity, the regioselective alkylation of arenes is still a challenging transformation in a lot of cases. Classical methods for the introduction of alkyl groups on arenes, which include the venerable Friedel‐Crafts reaction, radical additions, metallation or pre‐functionalization of the arene, as well as alternatives such as the directed alkylation of C‐H bonds, still suffer from severe limitations in terms of scope, efficiency and selectivity. This can be addressed by exploiting the innate reactivity of some (hetero)arenes, in which electronic and steric properties, governed (or not) by the presence of one (or multiple) heteroatom(s) ensure high levels of regioselectivity. These innate alkylations of C‐H bonds in (hetero)arenes will be overviewed, in a comprehensive manner, in this review article.Keywords
Funding Information
- Vrije Universiteit Brussel
- Fonds De La Recherche Scientifique - FNRS (PDR T.0160.18, EOS n° O019618F - ID EOS: 3092231)
- Fonds pour la Formation à la Recherche dans l’Industrie et dans l’Agriculture
This publication has 282 references indexed in Scilit:
- Practical and innate carbon–hydrogen functionalization of heterocyclesNature, 2012
- Visible‐Light Photoredox Catalysis in FlowAngewandte Chemie, 2012
- Direct Alkylation of Heteroaryls Using Potassium Alkyl- and AlkoxymethyltrifluoroboratesOrganic Letters, 2011
- Iron-Catalyzed Heterocycle and Arene Deprotonative AlkylationOrganic Letters, 2010
- A review of new developments in the Friedel–Crafts alkylation – From green chemistry to asymmetric catalysisBeilstein Journal of Organic Chemistry, 2010
- Rhodium catalyzed enantioselective cyclization of substituted imidazoles via C–H bond activationChemical Communications, 2009
- Direct Functionalization of Nitrogen Heterocycles via Rh-Catalyzed C−H Bond ActivationAccounts of Chemical Research, 2008
- Rh(I)-Catalyzed Alkylation of Quinolines and Pyridines via C−H Bond ActivationJournal of the American Chemical Society, 2007
- Direct transition metal-catalyzed functionalization of heteroaromatic compoundsChemical Society Reviews, 2007
- Synthesis of Potent Bicyclic Bisarylimidazole c-Jun N-Terminal Kinase Inhibitors by Catalytic C−H Bond ActivationJournal of the American Chemical Society, 2006