Oligosubstituted Pyrroles Directly from Substituted Methyl Isocyanides and Acetylenes
- 18 December 2008
- journal article
- Published by Wiley in Chemistry – A European Journal
- Vol. 15 (1), 227-236
- https://doi.org/10.1002/chem.200801395
Abstract
The formal cycloaddition of α‐metallated methyl isocyanides 1 onto the triple bond of electron‐deficient acetylenes 2 represents a direct and convenient approach to oligosubstituted pyrroles 3. The scope and limitations of this reaction (24 examples, 25–97 % yield) are reported along with an optimization of the reaction conditions and a rationalization of the mechanism. In addition, a related newly developed CuI‐mediated synthesis of 2,3‐disubstituted pyrroles by the reaction of copper acetylides derived from unactivated terminal alkynes with substituted methyl isocyanides is described (11 examples, 5–88 %yield).Keywords
This publication has 102 references indexed in Scilit:
- Pyrrole Synthesis Catalyzed by AgOTf or Cationic Au(I) ComplexesThe Journal of Organic Chemistry, 2006
- Total Synthesis of the Marine Natural Product rac‐DibromophakellstatinAngewandte Chemie International Edition, 2005
- 3-Methyl pyrrole-2,4-dicarboxylic acid 2-propyl ester 4-(1,2,2-trimethyl-propyl) ester: an exploration of the C-2 position. Part IIl Farmaco, 2004
- Naked-Eye Detection of Anions in Dichloromethane: Colorimetric Anion Sensors Based on Calix[4]pyrroleAngewandte Chemie, 2000
- Simple Synthesis of a Chlorin - Fullerene Dyad with a Novel Ring-Closure ReactionAngewandte Chemie International Edition, 2000
- Atropisomerism in polymers. Screw-sense selective polymerization of isocyanides by inhibiting the growth of one enantiomer of a racemic pair of helicesJournal of the American Chemical Society, 1988
- tert-Butoxycopper-carbonyl and tert-butoxycopper-tert-butyl isocyanide. New and sublimable copper-carbonyl and isocyanide complexesJournal of the American Chemical Society, 1974
- Systematic preparation and characterization of pentahaptocyclopentadienylcopper(I) compoundsJournal of the American Chemical Society, 1970
- Synthetic Reactions by a Complex Catalyst. VI. A Novel Hydrosilation of Isocyanide by Copper CatalystJournal of the American Chemical Society, 1967
- Cyclopentadienyl-triethylphosphine-copper(I) and bis-cyclopentadienylmercury(II)Journal of Inorganic and Nuclear Chemistry, 1956