Carbocations as Lewis Acid Catalysts: Scope and Reactivity
2015 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 357, no 1, 148-158 p.Article in journal (Refereed) Published
One class of potential Lewis acids that has received negligible attention as a catalyst is the carbocation. Here we show the potential of triarylmethylium ions as highly powerful Lewis acid catalysts for organic reactions. The Lewis acidity of the triarylmethylium ion can be easily tuned by variation of the electronic properties of the aromatic rings and the catalytic activity of the carbocation is shown to correlate directly to the level of stabilization of the empty p(C)-orbital at the cationic carbon. The versatility of triarylmethylium ions as efficient Lewis acid catalysts for organic reactions is demonstrated in Diels-Alder, aza-Diels-Alder, conjugate addition, halogenation, epoxide rearrangement and intramolecular hetro-ene reactions.
Place, publisher, year, edition, pages
2015. Vol. 357, no 1, 148-158 p.
carbocations, catalysis, Lewis acids, organocatalysis, trityl group
IdentifiersURN: urn:nbn:se:kth:diva-144522DOI: 10.1002/adsc.201400609ISI: 000347705400018ScopusID: 2-s2.0-84920733647OAI: oai:DiVA.org:kth-144522DiVA: diva2:713894
Updated from manuscript to article.
QC 201503062014-04-242014-04-242015-03-06Bibliographically approved