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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| Format: | Article |
| Language: | English |
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MDPI AG
2023-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/10/4095 |
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| author | Fatima Tuz Zahra Aamer Saeed Khansa Mumtaz Fernando Albericio |
| author_facet | Fatima Tuz Zahra Aamer Saeed Khansa Mumtaz Fernando Albericio |
| author_sort | Fatima Tuz Zahra |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-11T03:27:46Z |
| format | Article |
| id | doaj.art-d2456a02bf5f4fc1ae7e22c3e2b9c414 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T03:27:46Z |
| publishDate | 2023-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-d2456a02bf5f4fc1ae7e22c3e2b9c4142023-11-18T02:39:11ZengMDPI AGMolecules1420-30492023-05-012810409510.3390/molecules28104095Tropylium Ion, an Intriguing Moiety in Organic ChemistryFatima Tuz Zahra0Aamer Saeed1Khansa Mumtaz2Fernando Albericio3Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, PakistanDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, PakistanDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, PakistanSchool of Chemistry and Physics, University of KwaZulu-Natal, Durban 4001, South AfricaThe 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.https://www.mdpi.com/1420-3049/28/10/4095tropylium cationtropylium tetrafluoroborateselectivityelectrophileorgano-catalystuniversal oxidant |
| spellingShingle | Fatima Tuz Zahra Aamer Saeed Khansa Mumtaz Fernando Albericio Tropylium Ion, an Intriguing Moiety in Organic Chemistry Molecules tropylium cation tropylium tetrafluoroborate selectivity electrophile organo-catalyst universal oxidant |
| title | Tropylium Ion, an Intriguing Moiety in Organic Chemistry |
| title_full | Tropylium Ion, an Intriguing Moiety in Organic Chemistry |
| title_fullStr | Tropylium Ion, an Intriguing Moiety in Organic Chemistry |
| title_full_unstemmed | Tropylium Ion, an Intriguing Moiety in Organic Chemistry |
| title_short | Tropylium Ion, an Intriguing Moiety in Organic Chemistry |
| title_sort | tropylium ion an intriguing moiety in organic chemistry |
| topic | tropylium cation tropylium tetrafluoroborate selectivity electrophile organo-catalyst universal oxidant |
| url | https://www.mdpi.com/1420-3049/28/10/4095 |
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