Visible-Light-Induced Formal [3+2] Cycloaddition for Pyrrole Synthesis under Metal-Free Conditions

A photocatalytic formal [3+2] cycloaddition of 2H‐azirines with alkynes has been achieved under irradiation by visible light in the presence of organic dye photocatalysts. This transformation provides efficient access to highly functionalized pyrroles in good yields and has been applied to the synth...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie 2014-05, Vol.126 (22), p.5759-5762
Main Authors: Xuan, Jun, Xia, Xu-Dong, Zeng, Ting-Ting, Feng, Zhu-Jia, Chen, Jia-Rong, Lu, Liang-Qiu, Xiao, Wen-Jing
Format: Article
Language:English
Subjects:
Alkynes
Chemistry
Cycloaddition
Cycloadditionen
Energy transfer
Farbstoffe
Heterocyclen
Merging
Photocatalysis
Photocatalysts
Photochemie
Pyrroles
Solar energy
Synthesemethoden
Synthesis
Transformations
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A photocatalytic formal [3+2] cycloaddition of 2H‐azirines with alkynes has been achieved under irradiation by visible light in the presence of organic dye photocatalysts. This transformation provides efficient access to highly functionalized pyrroles in good yields and has been applied to the synthesis of drug analogues. A primary trial of photocascade catalysis merging energy transfer and redox neutral reactions was shown to be successful. Sichtbare Resultate: Die Titelreaktion in Gegenwart eines organischen Farbstoffs verbindet 2H‐Azirine und Alkine effizient und in guten Ausbeuten zu hoch funktionalisierten Pyrrolen. Sie wurde in einer formalen Synthese eines Inhibitors der HMG‐CoA‐Reduktase eingesetzt.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201400602