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

Authors
  • Qiu, Guanyinsheng
  • Wang, Qian
  • Zhu, Jieping
Publication Date
Jan 10, 2017
Identifiers
DOI: 10.1021/acs.orglett.6b03592
OAI: oai:infoscience.tind.io:224330
Source
Infoscience @ EPFL
License
Unknown
External links

Abstract

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.

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