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. Palladium-Catalyzed Three-Component Reaction of Propargyl Carbonates, Isocyanides, and Alcohols or Water: Switchable Synthesis of Pyrroles and Its Bicyclic Analogues
 
research article

Palladium-Catalyzed Three-Component Reaction of Propargyl Carbonates, Isocyanides, and Alcohols or Water: Switchable Synthesis of Pyrroles and Its Bicyclic Analogues

Qiu, Guanyinsheng  
•
Wang, Qian  
•
Zhu, Jieping  
2017
Organic Letters

In the presence of a catalytic amount of Pd(OAc)2 and a stoichiometric amount of tert-butylamine, the reaction of propargyl carbonates, isocyanides, and alcohols afforded polysubstituted aminopyrroles in good yields. Using water as a nucleophile instead of alcohol, the same reaction provided 1,4-dihydro-6H-furo[3,4-b]pyrrol-6-imines. A triple isocyanide insertion to the hypothetic (σ-allenyl)palladium(II) intermediate was involved in these ABC3-type multicomponent reactions. The key role of tert-butylamine was accounted for by its reaction with in situ generated carbon dioxide to form the carbamic acid, which in turn served as a nucleophile to trap the nitrilium intermediate.

  • Details
  • Metrics
Type
research article
DOI
10.1021/acs.orglett.6b03592
Web of Science ID

WOS:000391781600069

Author(s)
Qiu, Guanyinsheng  
Wang, Qian  
Zhu, Jieping  
Date Issued

2017

Publisher

American Chemical Society

Published in
Organic Letters
Volume

19

Issue

1

Start page

270

End page

273

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LSPN  
Available on Infoscience
January 10, 2017
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/132768
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