Repository logo

Infoscience

  • English
  • French
Log In
Logo EPFL, École polytechnique fédérale de Lausanne

Infoscience

  • English
  • French
Log In
  1. Home
  2. Academic and Research Output
  3. Journal articles
  4. Synthesis of Quinolines via the Metal-free Visible-Light-Mediated Radical Azidation of Cyclopropenes
 
research article

Synthesis of Quinolines via the Metal-free Visible-Light-Mediated Radical Azidation of Cyclopropenes

Smyrnov, Vladyslav  
•
Muriel, Bastian  
•
Waser, Jerome  
July 16, 2021
Organic Letters

We report the synthesis of quinolines using cyclopropenes and an azidobenziodazolone (ABZ) hypervalent iodine reagent as an azide radical source under visible-light irradiation. Multisubstituted quinoline products were obtained in 34-81% yield. The reaction was most efficient for 3-trifluoromethylcyclopropenes, affording valuable 4-trifluoromethylquinolines. The transformation probably proceeds through the cyclization of an iminyl radical formed by the addition of the azide radical on the cyclopropene double bond, followed by ring-opening and fragmentation.

  • Files
  • Details
  • Metrics
Loading...
Thumbnail Image
Name

OL2021-5435GreenAccess1.pdf

Type

Preprint

Version

Submitted version (Preprint)

Access type

openaccess

License Condition

CC BY

Size

7.35 MB

Format

Adobe PDF

Checksum (MD5)

b2953f04b81600a7437c1fbce2f73f34

Loading...
Thumbnail Image
Name

OL2021-5435GreenAccess.pdf

Type

Postprint

Version

Accepted version

Access type

embargo

Embargo End Date

2022-06-25

License Condition

CC BY

Size

7.46 MB

Format

Adobe PDF

Checksum (MD5)

16dd73ec35093fcf33d35a13fd70d4bf

Logo EPFL, École polytechnique fédérale de Lausanne
  • Contact
  • infoscience@epfl.ch

  • Follow us on Facebook
  • Follow us on Instagram
  • Follow us on LinkedIn
  • Follow us on X
  • Follow us on Youtube
AccessibilityLegal noticePrivacy policyCookie settingsEnd User AgreementGet helpFeedback

Infoscience is a service managed and provided by the Library and IT Services of EPFL. © EPFL, tous droits réservés