Catalytic Multicomponent Reactions for the Synthesis of N-Aryl Trisubstituted Pyrroles

Dirhodium(II) salts efficiently catalyze the three-component assembly reaction of an imine, diazoacetonitrile (DAN), and an activated alkynyl coupling partner to form substituted 1,2-diarylpyrroles in moderate to good yields. The transition-metal-catalyzed decomposition of the diazo compound in the...

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Bibliographic Details
Published in:Journal of organic chemistry 2007-03, Vol.72 (5), p.1811-1813
Main Authors: Galliford, Chris V, Scheidt, Karl A
Format: Article
Language:English
Subjects:
Catalysis
Cyclization
Heterocyclic Compounds - chemical synthesis
Imines - chemical synthesis
Magnetic Resonance Spectroscopy
Mass Spectrometry
Pyrroles - chemical synthesis
Rhodium - chemistry
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Summary:Dirhodium(II) salts efficiently catalyze the three-component assembly reaction of an imine, diazoacetonitrile (DAN), and an activated alkynyl coupling partner to form substituted 1,2-diarylpyrroles in moderate to good yields. The transition-metal-catalyzed decomposition of the diazo compound in the presence of the imine presumably generates a transient azomethine ylide that undergoes cycloaddition with dipolarophiles in a highly convergent manner.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo0624086