Microwave-Promoted Pd-Catalyzed Cyanation of Aryl Triflates:  A Fast and Versatile Access to 3-Cyano-3-desoxy-10-ketomorphinans

Microwave-Promoted Pd-Catalyzed Cyanation of Aryl Triflates:  A Fast and Versatile Access to 3-Cyano-3-desoxy-10-ketomorphinans

A methodology for the microwave-promoted conversion of triflates to the corresponding nitriles by using 8% equiv of Pd(Ph3P)4 as the catalyst and 2.0 equiv of Zn(CN)2 as the cyanide source has been developed. This method is highly efficient for the preparation of 3-cyano-3-desoxy-10-ketomorphinans....

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Veröffentlicht in:Organic letters 2003-01, Vol.5 (2), p.201-203
Hauptverfasser: Zhang, Ao, Neumeyer, John L
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Cyanides - chemistry
Ligands
Mesylates - chemistry
Microwaves
Narcotic Antagonists
Nitriles - chemical synthesis
Palladium
Receptors, Opioid - agonists
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Zusammenfassung:A methodology for the microwave-promoted conversion of triflates to the corresponding nitriles by using 8% equiv of Pd(Ph3P)4 as the catalyst and 2.0 equiv of Zn(CN)2 as the cyanide source has been developed. This method is highly efficient for the preparation of 3-cyano-3-desoxy-10-ketomorphinans. The reaction was generally completed in 15 min at 200 °C and produced products in greater than 86% yields.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol027256p