Carbocations as Lewis Acid Catalysts: Reactivity and Scope. Issue 1 (25th November 2014)

• Record Type: Journal Article
• Authors: Bah, Juho; Naidu, Veluru Ramesh; Teske, Johannes; Franzén, Johan
• Is Part Of: Advanced synthesis & catalysis. Volume 357:Issue 1(2015)
• Page Start: 148
• Page End: 158
• Publication Date: 2014-11-25
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201400609
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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 <italic>p</italic>_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.</p> <p> <boxed-text content-type="graphic" position="anchor" orientation="portrait"> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgh31s3mnhc" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </boxed-text> </p> </abstract>