A Highly Active System for the Metal-Free Aerobic Photocyanation of Tertiary Amines with Visible Light: Application to the Synthesis of Tetraponerines and CrispineA
- Publikationstyp:
- Zeitschriftenaufsatz
- Metadaten:
-
- Autoren
- Julio Cesar Orejarena Pacheco
- Alexander Lipp
- Alexander M Nauth
- Fabian Acke
- Jule-Philipp Dietz
- Till Opatz
- Autoren-URL
- https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000373483600044&DestLinkType=FullRecord&DestApp=WOS_CPL
- DOI
- 10.1002/chem.201504845
- eISSN
- 1521-3765
- Externe Identifier
- Clarivate Analytics Document Solution ID: DI4QE
- PubMed Identifier: 26929114
- ISSN
- 0947-6539
- Ausgabe der Veröffentlichung
- 15
- Zeitschrift
- CHEMISTRY-A EUROPEAN JOURNAL
- Schlüsselwörter
- alkaloids
- amines
- aminonitriles
- photocatalysis
- total synthesis
- Paginierung
- 5409 - 5415
- Datum der Veröffentlichung
- 2016
- Status
- Published
- Titel
- A Highly Active System for the Metal-Free Aerobic Photocyanation of Tertiary Amines with Visible Light: Application to the Synthesis of Tetraponerines and CrispineA
- Sub types
- Article
- Ausgabe der Zeitschrift
- 22
Datenquelle: Web of Science (Lite)
- Andere Metadatenquellen:
-
- Abstract
- <jats:title>Abstract</jats:title><jats:p>A highly efficient metal‐free catalytic system for the aerobic photocyanation of tertiary amines with visible light is reported. The use of air as terminal oxidant offers an improved safety profile compared with pure oxygen, the used compact fluorescent lamp (CFL) light sources are highly economical, and no halogenated solvents are required. This system not only proves to be effective for a wide variety of trialkylamines, pharmaceuticals, and alkaloids but remarkably also allows the lowest catalyst loading (0.00001 mol % or 0.1 ppm) ever reported for an organic dye. Bruylants reactions and C‐alkylation/decyanations were performed on the obtained α‐aminonitriles to demonstrate the postfunctionalization of complex molecules. The catalytic system is furthermore applied in the short and effective syntheses of the alkaloids (±)‐crispine A and the tetraponerines T7 and T8.</jats:p>
- Autoren
- Julio Cesar Orejarena Pacheco
- Alexander Lipp
- Alexander M Nauth
- Fabian Acke
- Jule‐Philipp Dietz
- Till Opatz
- DOI
- 10.1002/chem.201504845
- eISSN
- 1521-3765
- ISSN
- 0947-6539
- Ausgabe der Veröffentlichung
- 15
- Zeitschrift
- Chemistry – A European Journal
- Sprache
- en
- Online publication date
- 2016
- Paginierung
- 5409 - 5415
- Datum der Veröffentlichung
- 2016
- Status
- Published
- Herausgeber
- Wiley
- Herausgeber URL
- http://dx.doi.org/10.1002/chem.201504845
- Datum der Datenerfassung
- 2023
- Titel
- A Highly Active System for the Metal‐Free Aerobic Photocyanation of Tertiary Amines with Visible Light: Application to the Synthesis of Tetraponerines and Crispine A
- Ausgabe der Zeitschrift
- 22
Datenquelle: Crossref
- Abstract
- A highly efficient metal-free catalytic system for the aerobic photocyanation of tertiary amines with visible light is reported. The use of air as terminal oxidant offers an improved safety profile compared with pure oxygen, the used compact fluorescent lamp (CFL) light sources are highly economical, and no halogenated solvents are required. This system not only proves to be effective for a wide variety of trialkylamines, pharmaceuticals, and alkaloids but remarkably also allows the lowest catalyst loading (0.00001 mol% or 0.1 ppm) ever reported for an organic dye. Bruylants reactions and C-alkylation/decyanations were performed on the obtained α-aminonitriles to demonstrate the postfunctionalization of complex molecules. The catalytic system is furthermore applied in the short and effective syntheses of the alkaloids (±)-crispine A and the tetraponerines T7 and T8.
- Addresses
- Institute of Organic Chemistry, University of Mainz, Duesbergweg 10-14, 55128, Mainz, Germany.
- Autoren
- Julio Cesar Orejarena Pacheco
- Alexander Lipp
- Alexander M Nauth
- Fabian Acke
- Jule-Philipp Dietz
- Till Opatz
- DOI
- 10.1002/chem.201504845
- eISSN
- 1521-3765
- Externe Identifier
- PubMed Identifier: 26929114
- Open access
- false
- ISSN
- 0947-6539
- Ausgabe der Veröffentlichung
- 15
- Zeitschrift
- Chemistry (Weinheim an der Bergstrasse, Germany)
- Schlüsselwörter
- Metals
- Amines
- Alkaloids
- Isoquinolines
- Molecular Structure
- Alkylation
- Oxidation-Reduction
- Catalysis
- Light
- Sprache
- eng
- Medium
- Print-Electronic
- Online publication date
- 2016
- Paginierung
- 5409 - 5415
- Datum der Veröffentlichung
- 2016
- Status
- Published
- Datum der Datenerfassung
- 2016
- Titel
- A Highly Active System for the Metal-Free Aerobic Photocyanation of Tertiary Amines with Visible Light: Application to the Synthesis of Tetraponerines and Crispine A.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 22
Datenquelle: Europe PubMed Central
- Abstract
- A highly efficient metal-free catalytic system for the aerobic photocyanation of tertiary amines with visible light is reported. The use of air as terminal oxidant offers an improved safety profile compared with pure oxygen, the used compact fluorescent lamp (CFL) light sources are highly economical, and no halogenated solvents are required. This system not only proves to be effective for a wide variety of trialkylamines, pharmaceuticals, and alkaloids but remarkably also allows the lowest catalyst loading (0.00001 mol% or 0.1 ppm) ever reported for an organic dye. Bruylants reactions and C-alkylation/decyanations were performed on the obtained α-aminonitriles to demonstrate the postfunctionalization of complex molecules. The catalytic system is furthermore applied in the short and effective syntheses of the alkaloids (±)-crispine A and the tetraponerines T7 and T8.
- Autoren
- Julio Cesar Orejarena Pacheco
- Alexander Lipp
- Alexander M Nauth
- Fabian Acke
- Jule-Philipp Dietz
- Till Opatz
- Autoren-URL
- https://www.ncbi.nlm.nih.gov/pubmed/26929114
- DOI
- 10.1002/chem.201504845
- eISSN
- 1521-3765
- Ausgabe der Veröffentlichung
- 15
- Zeitschrift
- Chemistry
- Schlüsselwörter
- alkaloids
- amines
- aminonitriles
- photocatalysis
- total synthesis
- Alkaloids
- Alkylation
- Amines
- Catalysis
- Isoquinolines
- Light
- Metals
- Molecular Structure
- Oxidation-Reduction
- Sprache
- eng
- Country
- Germany
- Paginierung
- 5409 - 5415
- Datum der Veröffentlichung
- 2016
- Status
- Published
- Datum, an dem der Datensatz öffentlich gemacht wurde
- 2016
- Titel
- A Highly Active System for the Metal-Free Aerobic Photocyanation of Tertiary Amines with Visible Light: Application to the Synthesis of Tetraponerines and Crispine A.
- Sub types
- Journal Article
- Ausgabe der Zeitschrift
- 22
Datenquelle: PubMed
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