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Versatile Direct Synthesis of Oligosubstituted Pyrroles by Cycloaddition of α-Metalated Isocyanides to Acetylenes

Oleg V. Larionov, Armin de Meijere*

*Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, 37077 Göttingen, Email:

O. V. Larionov, A. de Meijere, Angew. Chem. Int. Ed., 2005, 44, 5664-5667.

DOI: 10.1002/anie.200502140I (free Supporting Information)


Various 2,3,4-trisubstituted pyrroles are easily accessible in one step from readily available acetylenes and acceptor-substituted methyl isocyanides by base-mediated or copper-catalyzed cycloadditions. Scope and limitations of both pyrrole syntheses are discussed.

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proposed mechanism

Key Words

cesium, copper, heterocycles, homogeneous catalysis, isocyanides, pyrroles

ID: J06-Y2005-1310