Microwave-promoted Pd-catalyzed cyanation of aryl triflates: a fast and versatile access to 3-cyano-3-desoxy-10-ketomorphinans.
[reaction: see text] A methodology for the microwave-promoted conversion of triflates to the corresponding nitriles by using 8% equiv of Pd(Ph(3)P)(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 degrees C and produced products in greater than 86% yields.
Zhang
Ao
A
Medicinal Chemistry Program, Alcohol and Drug Abuse Research Center, McLean Hospital, Harvard Medical School, 115 Mill Street, Belmont, Massachusetts 02478, USA.
Neumeyer
John L
JL
D002384:Catalysis; D003486:Cyanides / Q000737:chemistry; D008024:Ligands; D008698:Mesylates / Q000737:chemistry; D008872:Microwaves; D009292:Narcotic Antagonists; D009570:Nitriles / Q000138:chemical synthesis*; D010165:Palladium; D011957:Receptors, Opioid / Q000819:agonists*
D003486:Cyanides; D008024:Ligands; D008698:Mesylates; D009292:Narcotic Antagonists; D009570:Nitriles; D011957:Receptors, Opioid; D010165:Palladium; C012077:trifluoromethanesulfonic acid