Powerful Fluoroalkoxy Molybdenum(V) Reagent for Selective Oxidative Arene Coupling Reaction

Publication type:
Journal article
Metadata:
Autoren
  • Moritz Schubert
  • Jana Leppin
  • Kathrin Wehming
  • Dieter Schollmeyer
  • Katja Heinze
  • Siegfried R Waldvogel
Autoren-URL
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000336834000025&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.1002/anie.201309287
eISSN
1521-3773
Externe Identifier
  • Clarivate Analytics Document Solution ID: AI4KL
  • PubMed Identifier: 24478061
ISSN
1433-7851
Ausgabe der Veröffentlichung
9
Zeitschrift
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Schlüsselwörter
  • arene coupling
  • C-C coupling
  • cyclization
  • molybdenum
  • oxidative coupling
Paginierung
2494 - 2497
Datum der Veröffentlichung
2014
Status
Published
Titel
Powerful Fluoroalkoxy Molybdenum(V) Reagent for Selective Oxidative Arene Coupling Reaction
Sub types
  • Article
Ausgabe der Zeitschrift
53

Data source: Web of Science (Lite)

Other metadata sources:
Abstract
<jats:title>Abstract</jats:title><jats:p>We introduce the novel fluoroalkoxy molybdenum(V) reagent <jats:bold>1</jats:bold> which has superior reactivity and selectivity in comparison to MoCl<jats:sub>5</jats:sub> or the MoCl<jats:sub>5</jats:sub>/TiCl<jats:sub>4</jats:sub> reagent mixture in the oxidative coupling reactions of aryls. Common side reactions, such as chlorination and/or oligomer formation, are drastically diminished creating a powerful and useful reagent for oxidative coupling. Theoretical treatment of the reagent interaction with 1,2‐dimethoxybenzene‐type substrates indicates an inner‐sphere electron transfer followed by a radical cationic reaction pathway for the oxidative‐coupling process. EPR spectroscopic and electrochemical studies, X‐ray analyses, computational investigations, and the experimental scope provide a highly consistent picture. The substitution of chlorido ligands by hexafluoroisopropoxido moieties seems to boost both the reactivity and selectivity of the metal center which might be applied to other reagents as well.</jats:p>
Autoren
  • Moritz Schubert
  • Jana Leppin
  • Kathrin Wehming
  • Dieter Schollmeyer
  • Katja Heinze
  • Siegfried R Waldvogel
DOI
10.1002/anie.201309287
eISSN
1521-3773
ISSN
1433-7851
Ausgabe der Veröffentlichung
9
Zeitschrift
Angewandte Chemie International Edition
Sprache
en
Online publication date
2014
Paginierung
2494 - 2497
Datum der Veröffentlichung
2014
Status
Published
Herausgeber
Wiley
Herausgeber URL
http://dx.doi.org/10.1002/anie.201309287
Datum der Datenerfassung
2023
Titel
Powerful Fluoroalkoxy Molybdenum(V) Reagent for Selective Oxidative Arene Coupling Reaction
Ausgabe der Zeitschrift
53

Data source: Crossref

Abstract
We introduce the novel fluoroalkoxy molybdenum(V) reagent 1 which has superior reactivity and selectivity in comparison to MoCl5 or the MoCl5 /TiCl4 reagent mixture in the oxidative coupling reactions of aryls. Common side reactions, such as chlorination and/or oligomer formation, are drastically diminished creating a powerful and useful reagent for oxidative coupling. Theoretical treatment of the reagent interaction with 1,2-dimethoxybenzene-type substrates indicates an inner-sphere electron transfer followed by a radical cationic reaction pathway for the oxidative-coupling process. EPR spectroscopic and electrochemical studies, X-ray analyses, computational investigations, and the experimental scope provide a highly consistent picture. The substitution of chlorido ligands by hexafluoroisopropoxido moieties seems to boost both the reactivity and selectivity of the metal center which might be applied to other reagents as well.
Addresses
  • Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, Duesbergweg 10-14, 55128 Mainz (Germany) http://www.chemie.uni-mainz.de/OC/AK-Waldvogel/
Autoren
  • Moritz Schubert
  • Jana Leppin
  • Kathrin Wehming
  • Dieter Schollmeyer
  • Katja Heinze
  • Siegfried R Waldvogel
DOI
10.1002/anie.201309287
eISSN
1521-3773
Externe Identifier
  • PubMed Identifier: 24478061
Open access
false
ISSN
1433-7851
Ausgabe der Veröffentlichung
9
Zeitschrift
Angewandte Chemie (International ed. in English)
Sprache
eng
Medium
Print-Electronic
Online publication date
2014
Paginierung
2494 - 2497
Datum der Veröffentlichung
2014
Status
Published
Datum der Datenerfassung
2014
Titel
Powerful fluoroalkoxy molybdenum(V) reagent for selective oxidative arene coupling reaction.
Sub types
  • Journal Article
Ausgabe der Zeitschrift
53

Data source: Europe PubMed Central

Abstract
We introduce the novel fluoroalkoxy molybdenum(V) reagent 1 which has superior reactivity and selectivity in comparison to MoCl5 or the MoCl5 /TiCl4 reagent mixture in the oxidative coupling reactions of aryls. Common side reactions, such as chlorination and/or oligomer formation, are drastically diminished creating a powerful and useful reagent for oxidative coupling. Theoretical treatment of the reagent interaction with 1,2-dimethoxybenzene-type substrates indicates an inner-sphere electron transfer followed by a radical cationic reaction pathway for the oxidative-coupling process. EPR spectroscopic and electrochemical studies, X-ray analyses, computational investigations, and the experimental scope provide a highly consistent picture. The substitution of chlorido ligands by hexafluoroisopropoxido moieties seems to boost both the reactivity and selectivity of the metal center which might be applied to other reagents as well.
Autoren
  • Moritz Schubert
  • Jana Leppin
  • Kathrin Wehming
  • Dieter Schollmeyer
  • Katja Heinze
  • Siegfried R Waldvogel
Autoren-URL
https://www.ncbi.nlm.nih.gov/pubmed/24478061
DOI
10.1002/anie.201309287
eISSN
1521-3773
Ausgabe der Veröffentlichung
9
Zeitschrift
Angew Chem Int Ed Engl
Schlüsselwörter
  • CC coupling
  • arene coupling
  • cyclization
  • molybdenum
  • oxidative coupling
Sprache
eng
Country
Germany
Paginierung
2494 - 2497
Datum der Veröffentlichung
2014
Status
Published
Datum, an dem der Datensatz öffentlich gemacht wurde
2014
Titel
Powerful fluoroalkoxy molybdenum(V) reagent for selective oxidative arene coupling reaction.
Sub types
  • Journal Article
Ausgabe der Zeitschrift
53

Data source: PubMed

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