Tropylium Ion, an Intriguing Moiety in Organic Chemistry

The tropylium ion is a non-benzenoid aromatic species that works as a catalyst. This chemical entity brings about a large number of organic transformations, such as hydroboration reactions, ring contraction, the trapping of enolates, oxidative functionalization, metathesis, insertion, acetalization,...

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Bibliographic Details
Published in:	Molecules (Basel, Switzerland) Vol. 28; no. 10; p. 4095
Main Authors:	Zahra, Fatima Tuz, Saeed, Aamer, Mumtaz, Khansa, Albericio, Fernando
Format:	Journal Article
Language:	English
Published:	Switzerland MDPI AG 15-05-2023 MDPI
Subjects:	Catalysis Catalysts Cations Chemical reactions Chemical tests and reagents electrophile Enolates Functional groups Hydroboration Hydrocarbons Literature reviews Macrocyclic compounds Metathesis Organic chemistry organo-catalyst Oxidation Reagents Review Salt selectivity Transition metals tropylium cation tropylium tetrafluoroborate universal oxidant selectivity coupling reagent tropylium tetrafluoroborate Lewis acid catalyst universal oxidant organo-catalyst electrophile tropylium cation
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Summary:	The tropylium ion is a non-benzenoid aromatic species that works as a catalyst. This chemical entity brings about a large number of organic transformations, such as hydroboration reactions, ring contraction, the trapping of enolates, oxidative functionalization, metathesis, insertion, acetalization, and trans-acetalization reactions. The tropylium ion also functions as a coupling reagent in synthetic reactions. This cation's versatility can be seen in its role in the synthesis of macrocyclic compounds and cage structures. Bearing a charge, the tropylium ion is more prone to nucleophilic/electrophilic reactions than neutral benzenoid equivalents. This ability enables it to assist in a variety of chemical reactions. The primary purpose of using tropylium ions in organic reactions is to replace transition metals in catalysis chemistry. It outperforms transition-metal catalysts in terms of its yield, moderate conditions, non-toxic byproducts, functional group tolerance, selectivity, and ease of handling. Furthermore, the tropylium ion is simple to synthesize in the laboratory. The current review incorporates the literature reported from 1950 to 2021; however, the last two decades have witnessed a phenomenal upsurge in the utilization of the tropylium ion in the facilitation of organic conversions. The importance of the tropylium ion as an environmentally safe catalyst in synthesis and a comprehensive summary of some important reactions catalyzed via tropylium cations are described.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 ObjectType-Review-3 content type line 23
ISSN:	1420-3049 1420-3049
DOI:	10.3390/molecules28104095