English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
  Direct Photoexcitation of Ethynylbenziodoxolones: An Alternative to Photocatalysis for Alkynylation Reactions

Amos, S. G. E., Cavalli, D., Le Vaillant, F., & Waser, J. (2021). Direct Photoexcitation of Ethynylbenziodoxolones: An Alternative to Photocatalysis for Alkynylation Reactions. Angewandte Chemie International Edition, 60(44), 23827-23834. doi:10.1002/anie.202110257.

Item is

Basic

show hide
Genre: Journal Article

Files

show Files

Locators

show

Creators

show
hide
 Creators:
Amos, Stephanie G. E.1, Author
Cavalli, Diana1, Author
Le Vaillant, Franck2, Author              
Waser, Jerome1, Author
Affiliations:
1Laboratory of Catalysis and Organic Synthesis and National Centre of Competence in Research (NCCR) Catalysis, Institut des Sciences et Ingénierie Chimique, Ecole Polytechnique Fédérale de Lausanne, CH-1015 Lausanne, Switzerland, ou_persistent22              
2Research Group Cornellà, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2466693              

Content

show
hide
Free keywords: alkynes; hypervalent iodine; photochemistry; quaternary centers; synthetic methods
 Abstract: Ethynylbenziodoxolones (EBXs) are commonly used as radical traps in photocatalytic alkynylations. Herein, we report that aryl-substituted EBX reagents can be directly activated by visible light irradiation. They act as both oxidants and radical traps, alleviating the need for a photocatalyst in several reported EBX-mediated processes, including decarboxylative and deboronative alkynylations, the oxyalkynylation of enamides and the C−H alkynylation of THF. Furthermore, the method could be applied to the synthesis of alkynylated quaternary centers from tertiary alcohols via stable oxalate salts and from tertiary amines via aryl imines. A photocatalytic process using 4CzIPN as an organic dye was also developed for the deoxyalkynylation of oxalates.

Details

show
hide
Language(s): eng - English
 Dates: 2021-07-312021-08-172021-10-25
 Publication Status: Published in print
 Pages: 8
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.202110257
 Degree: -

Event

show

Legal Case

show

Project information

show

Source 1

show
hide
Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 60 (44) Sequence Number: - Start / End Page: 23827 - 23834 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851