Radical addition to iminium ions and cationic heterocycles
- Publikationstyp:
- Zeitschriftenaufsatz
- Metadaten:
-
- Autoren
- Johannes Tauber
- Dennis Imbri
- Till Opatz
- Sammlungen
- metadata
- ISSN
- 1420-3049
- Ausgabe der Veröffentlichung
- 10
- Zeitschrift
- Molecules
- Schlüsselwörter
- 540 Chemie
- 540 Chemistry and allied sciences
- Sprache
- eng
- Paginierung
- Seiten: 16190 - 16222
- Datum der Veröffentlichung
- 2014
- Herausgeber
- MDPI
- Herausgeber URL
- http://dx.doi.org/10.3390/molecules191016190
- Datum der Datenerfassung
- 2020
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2020
- Zugang
- Public
- Titel
- Radical addition to iminium ions and cationic heterocycles
- Ausgabe der Zeitschrift
- 19
Datenquelle: METADATA.UB
- Andere Metadatenquellen:
-
- Autoren
- Johannes Tauber
- Dennis Imbri
- Till Opatz
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000344456100047&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.3390/molecules191016190
- eISSN
- 1420-3049
- Externe Identifier
- Clarivate Analytics Document Solution ID: AS7SX
- PubMed Identifier: 25310148
- Ausgabe der Veröffentlichung
- 10
- Zeitschrift
- MOLECULES
- Schlüsselwörter
- radicals
- iminium salts
- heterocycles
- addition reactions
- rearrangements
- Minisci reaction
- Porta reaction
- photoredox catalysis
- transition metal catalysis
- late-stage functionalization
- Paginierung
- 16190 - 16222
- Datum der Veröffentlichung
- 2014
- Status
- Published
- Titel
- Radical Addition to Iminium Ions and Cationic Heterocycles
- Sub types
- Review
- Ausgabe der Zeitschrift
- 19
Datenquelle: Web of Science (Lite)
- Abstract
- <jats:p>Carbon-centered radicals represent highly useful reactive intermediates in organic synthesis. Their nucleophilic character is reflected by fast additions to electron deficient C=X double bonds as present in iminium ions or cationic heterocycles. This review covers diverse reactions of preformed or in situ-generated cationic substrates with various types of C-radicals, including alkyl, alkoxyalkyl, trifluoromethyl, aryl, acyl, carbamoyl, and alkoxycarbonyl species. Despite its high reactivity, the strong interaction of the radical’s SOMO with the LUMO of the cation frequently results in a high regioselectivity. Intra- and intermolecular processes such as the Minisci reaction, the Porta reaction, and the Knabe rearrangement will be discussed along with transition metal and photoredox catalysis or electrochemical methods to generate the odd-electron species.</jats:p>
- Autoren
- Johannes Tauber
- Dennis Imbri
- Till Opatz
- DOI
- 10.3390/molecules191016190
- eISSN
- 1420-3049
- Ausgabe der Veröffentlichung
- 10
- Zeitschrift
- Molecules
- Sprache
- en
- Online publication date
- 2014
- Paginierung
- 16190 - 16222
- Status
- Published online
- Herausgeber
- MDPI AG
- Herausgeber URL
- http://dx.doi.org/10.3390/molecules191016190
- Datum der Datenerfassung
- 2024
- Titel
- Radical Addition to Iminium Ions and Cationic Heterocycles
- Ausgabe der Zeitschrift
- 19
Datenquelle: Crossref
- Abstract
- Carbon-centered radicals represent highly useful reactive intermediates in organic synthesis. Their nucleophilic character is reflected by fast additions to electron deficient C=X double bonds as present in iminium ions or cationic heterocycles. This review covers diverse reactions of preformed or in situ-generated cationic substrates with various types of C-radicals, including alkyl, alkoxyalkyl, trifluoromethyl, aryl, acyl, carbamoyl, and alkoxycarbonyl species. Despite its high reactivity, the strong interaction of the radical's SOMO with the LUMO of the cation frequently results in a high regioselectivity. Intra- and intermolecular processes such as the Minisci reaction, the Porta reaction, and the Knabe rearrangement will be discussed along with transition metal and photoredox catalysis or electrochemical methods to generate the odd-electron species.
- Addresses
- Institute of Organic Chemistry, Johannes Gutenberg-University Mainz, Duesbergweg 10-14, 55128 Mainz, Germany.
- Autoren
- Johannes Tauber
- Dennis Imbri
- Till Opatz
- DOI
- 10.3390/molecules191016190
- eISSN
- 1420-3049
- Externe Identifier
- PubMed Identifier: 25310148
- PubMed Central ID: PMC6270771
- Open access
- true
- ISSN
- 1420-3049
- Ausgabe der Veröffentlichung
- 10
- Zeitschrift
- Molecules (Basel, Switzerland)
- Schlüsselwörter
- Ions
- Cations
- Carbon
- Heterocyclic Compounds
- Catalysis
- Models, Chemical
- Sprache
- eng
- Medium
- Electronic
- Online publication date
- 2014
- Open access status
- Open Access
- Paginierung
- 16190 - 16222
- Datum der Veröffentlichung
- 2014
- Status
- Published
- Publisher licence
- CC BY
- Datum der Datenerfassung
- 2014
- Titel
- Radical addition to iminium ions and cationic heterocycles.
- Sub types
- review-article
- Review
- Journal Article
- Ausgabe der Zeitschrift
- 19
Files
https://www.mdpi.com/1420-3049/19/10/16190/pdf?version=1412941520 https://europepmc.org/articles/PMC6270771?pdf=render
Datenquelle: Europe PubMed Central
- Abstract
- Carbon-centered radicals represent highly useful reactive intermediates in organic synthesis. Their nucleophilic character is reflected by fast additions to electron deficient C=X double bonds as present in iminium ions or cationic heterocycles. This review covers diverse reactions of preformed or in situ-generated cationic substrates with various types of C-radicals, including alkyl, alkoxyalkyl, trifluoromethyl, aryl, acyl, carbamoyl, and alkoxycarbonyl species. Despite its high reactivity, the strong interaction of the radical's SOMO with the LUMO of the cation frequently results in a high regioselectivity. Intra- and intermolecular processes such as the Minisci reaction, the Porta reaction, and the Knabe rearrangement will be discussed along with transition metal and photoredox catalysis or electrochemical methods to generate the odd-electron species.
- Date of acceptance
- 2014
- Autoren
- Johannes Tauber
- Dennis Imbri
- Till Opatz
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/25310148
- DOI
- 10.3390/molecules191016190
- eISSN
- 1420-3049
- Externe Identifier
- PubMed Central ID: PMC6270771
- Ausgabe der Veröffentlichung
- 10
- Zeitschrift
- Molecules
- Schlüsselwörter
- Carbon
- Catalysis
- Cations
- Heterocyclic Compounds
- Ions
- Models, Chemical
- Sprache
- eng
- Country
- Switzerland
- Paginierung
- 16190 - 16222
- PII
- molecules191016190
- Datum der Veröffentlichung
- 2014
- Status
- Published online
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2015
- Titel
- Radical addition to iminium ions and cationic heterocycles.
- Sub types
- Journal Article
- Review
- Ausgabe der Zeitschrift
- 19
Datenquelle: PubMed
- Author's licence
- CC-BY
- Autoren
- Johannes Tauber
- Dennis Imbri
- Till Opatz
- Hosting institution
- Universitätsbibliothek Mainz
- Sammlungen
- DFG-OA-Publizieren (2012 - 2017)
- Resource version
- Published version
- DOI
- 10.3390/molecules191016190
- Funding acknowledgements
- DFG, Open Access-Publizieren Universität Mainz / Universitätsmedizin
- File(s) embargoed
- false
- Open access
- true
- ISSN
- 1420-3049
- Ausgabe der Veröffentlichung
- 10
- Zeitschrift
- Molecules
- Schlüsselwörter
- 540 Chemie
- 540 Chemistry and allied sciences
- Sprache
- eng
- Open access status
- Open Access
- Paginierung
- 16190 - 16222
- Datum der Veröffentlichung
- 2014
- Public URL
- https://openscience.ub.uni-mainz.de/handle/20.500.12030/7427
- Herausgeber
- MDPI
- Herausgeber URL
- http://dx.doi.org/10.3390/molecules191016190
- Datum der Datenerfassung
- 2022
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2022
- Zugang
- Public
- Titel
- Radical addition to iminium ions and cationic heterocycles
- Ausgabe der Zeitschrift
- 19
Files
radical_addition_to_iminium_i-20220712205636286.pdf
Datenquelle: OPENSCIENCE.UB
- Beziehungen:
- Eigentum von