Pyrrole Synthesis via Allylic sp(3) C-H Activation of Enamines Followed by Intermolecular Coupling with Unactivated Alkynes
Rakshit S, Patureau FW, Glorius F
Research article (journal)Abstract
A conceptually novel pyrrole synthesis is reported, efficiently merging enamines and (unactivated) alkynes under oxidative conditions. In an intermolecular Rh catalyzed process, the challenging allylic sp(3) C-H activation of the enamine substrates is followed by the cyclization with the alkyne (R-3 = CO2R). Alternatively, in some cases (R-3 = CN), the enamine can be utilized for a vinylic sp(2) C-H activation. A total of 17 examples with yields above 60% is presented, together with the results of an initial mechanistic investigation.
Details about the publication
Journal: Journal of the American Chemical Society (J. Am. Chem. Soc.)
Volume: 132
Issue: 28
Page range: 9585-9587
Status: Published
Release year: 2010 (21/07/2010)
Language in which the publication is written: English
DOI: 10.1021/ja104305s
Keywords: n-aryl enamines bond formation efficient synthesis polysubstituted pyrroles containing heterocycles substituted pyrroles catalyzed reaction internal alkynes indoles functionalization
Authors from the University of Münster
| Glorius, Frank | Professur für Organische Chemie (Prof. Glorius) |
| Rakshit, Souvik | Organic Chemistry Institute |