Copper- or Phosphine-Catalyzed Reaction of Alkynes with Isocyanides. Regioselective Synthesis of Substituted Pyrroles Controlled by the Catalyst

Copper- or Phosphine-Catalyzed Reaction of Alkynes with Isocyanides. Regioselective Synthesis of Substituted Pyrroles Controlled by the Catalyst

The copper-catalyzed reaction of isocyanides (CNCH2EWG1) 1 with electron-deficient alkynes (RC≡CEWG2) 2 gave the 2,4-di-EWG-substituted pyrroles 3 selectively, whereas the phosphine-catalyzed reaction of 1 with 2 afforded the 2,3-di-EWG-subsituted pyrroles 4. Accordingly, regioselective synthesis of...

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Veröffentlicht in:Journal of the American Chemical Society 2005-06, Vol.127 (25), p.9260-9266
Hauptverfasser: Kamijo, Shin, Kanazawa, Chikashi, Yamamoto, Yoshinori
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes - chemistry
Catalysis
Chemical reactivity
Chemistry
Copper - chemistry
Cyanides - chemistry
Exact sciences and technology
Molecular Structure
Organic chemistry
Phosphines - chemistry
Pyrroles - chemical synthesis
Pyrroles - chemistry
Reactivity and mechanisms
Stereoisomerism
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Zusammenfassung:The copper-catalyzed reaction of isocyanides (CNCH2EWG1) 1 with electron-deficient alkynes (RC≡CEWG2) 2 gave the 2,4-di-EWG-substituted pyrroles 3 selectively, whereas the phosphine-catalyzed reaction of 1 with 2 afforded the 2,3-di-EWG-subsituted pyrroles 4. Accordingly, regioselective synthesis of substituted pyrroles has been achieved by merely choosing the catalyst.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja051875m