Affiliation:
1. Organic Chemistry Institute, University of Zürich, Winterthurerstrasse 190, Zürich CH-8057, Switzerland.
Abstract
Putting the F in Friedel-Crafts
The Friedel-Crafts class of reactions, among the oldest and most broadly applied in organic chemistry, form carbon-carbon bonds between aromatic rings and a variety of non-aromatic substituents, such as alkyl groups. Generally, a metal complex is used to activate chlorinated or brominated precursors of these substituents, but by using silicon-based reagents to activate a fluorinated precursor,
Allemann
et al.
(p.
574
) extend the reaction to coupling of two different aromatic sites, leading to efficient formation of elaborate polycyclic structures. The method relies on the unusual strength of silicon-fluorine bonds as a driving force.
Publisher
American Association for the Advancement of Science (AAAS)
Reference32 articles.
1. G. A. Olah Friedel-Crafts Chemistry (Wiley New York 1973).
2. R. M. Roberts A. A. Khalaf Friedel-Crafts Alkylation Chemistry: A Century of Discovery (Dekker New York 1984).
3. H.-G. Franck J. W. Stadelhofer Industrial Aromatic Chemistry (Springer-Verlag Berlin 1988).
4. Acylation, methylation, and carboxyalkylation of olefins by Group VIII metal derivatives
5. Z. Rappoport P. Stang Eds. Dicoordinated Carbocations (Wiley New York 1997).
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