English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
 
 
DownloadE-Mail
  Sulfonic Acid-Catalyzed Autoxidative Carbon-Carbon Coupling Reaction under Elevated Partial Pressure of Oxygen

Pintér, Á., & Klussmann, M. (2012). Sulfonic Acid-Catalyzed Autoxidative Carbon-Carbon Coupling Reaction under Elevated Partial Pressure of Oxygen. Advanced Synthesis and Catalysis, (354), 701-711. doi:10.1002/adsc.201100563.

Item is

Files

show Files

Locators

show

Creators

show
hide
 Creators:
Pintér, Áron1, Author              
Klussmann, Martin1, Author              
Affiliations:
1Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society, Kaiser-Wilhelm-Platz 1, 45470 Mülheim an der Ruhr, DE, ou_1445608              

Content

show
hide
Free keywords: autoxidation; Bronsted acid catalysis; C?C coupling; C?H activation; high-pressure chemistry; oxygen
 Abstract: An aerobic organocatalytic oxidative CC bond formation reaction of benzylic CH bonds with various C-nucleophiles is described. The coupling reaction proceeds by simply stirring the substrates under elevated partial pressure of oxygen in the presence of a sulfonic acid catalyst at room temperature. Elevation of the pressure enables the reaction of a broad scope of nucleophile substrates otherwise showing poor reactivity at ambient pressure. The benzylic CH bonds of xanthene, acridanes, isochromane and related heterocycles could be functionalized with nucleophiles including ketones, 1,3-dicarbonyl compounds and aldehydes. Electron-rich arenes could be utilized as nucleophiles at elevated temperatures. The reactions are believed to proceed via autoxidation of the benzylic CH bonds to the hydroperoxides and subsequent nucleophilic substitution catalyzed by sulfonic acids.

Details

show
hide
Language(s):
 Dates: 2012-03-02
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/adsc.201100563
 Degree: -

Event

show

Legal Case

show

Project information

show

Source 1

show
hide
Title: Advanced Synthesis and Catalysis
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: Weinheim, Fed. Rep. of Germany : Wiley-VCH Verlag GmbH
Pages: - Volume / Issue: (354) Sequence Number: - Start / End Page: 701 - 711 Identifier: ISSN: 1615-4150
CoNE: https://pure.mpg.de/cone/journals/resource/958634688013