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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 3
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Original Articles

Application of Polymer‐Supported Triphenylphosphine and Microwave Irradiation to the Palladium‐Catalyzed Cyanation of Aryl Triflates

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Pages 431-438 | Received 19 Feb 2006, Published online: 06 Feb 2007

References

  • Larock , R. C. 1989 . Comprehensive Organic Transformations. A Guide to Functional Group Preparations New York : VCH Publishers .
  • Connell , R. , Scavo , F. , Helquist , P. and Akermark , B. 1986 . Functionalized oxazoles from rhodium‐catalyzed reaction of dimethyl diazomalonate with nitriles . Tetrahedron Lett. , 27 : 5559 – 5562 .
  • Kerdesky , F. A. J. , Holms , J. H. , Moore , J. L. , Bell , R. L. , Dyer , R. D. , Carter , G. W. and Brooks , D. W. 1991 . 4‐Hydroxythiazole inhibitors of 5‐lipoxygenase . J. Med. Chem. , 34 : 2158 – 2165 .
  • Gelotte , K. O. , Mason , D. N. , Meckler , H. , Shieh , W.‐C. and Starkey , C. M. 1990 . An efficient synthesis of the novel triazoloquinazoline adenosine antagonist, CGS 15943 . J. Heterocycl Chem. , 27 : 1549 – 1552 .
  • Menzler , S. , Bikker , J. A. , Suman‐Chauhan , N. and Horwell , D. C. 2000 . Design and bilogical evaluation of non‐peptide analogues of omega‐conotoxin MVIIA . Bioorg. Med. Chem. Lett. , 10 : 345 – 347 .
  • Amantini , D. , Beleggia , R. , Fringuelli , F. , Pizzo , F. and Vaccaro , L. 2004 . TBAF‐catalyzed synthesis of 5‐substituted 1H‐tetrazoles under solventless conditions . J. Org. Chem. , 69 : 2896 – 2898 .
  • Herr , R. J. 2002 . 5‐Substituted‐1H‐tetrazoles as carboxylic acid isosteres: Medicinal chemistry and synthetic methods . Bioorg. Med. Chem. , 10 : 3379 – 3393 .
  • Rosenmund , K. W. and Struck , E. 1919 . Das am Ringkohlensoff gebundene halogen und sein ersatz durch andere substituenten. I. Mitteilung: Ersatz des halogens durch die Carboxylgruppe . Chem. Ber. , 52 : 1749
  • Arvela , R. K. and Leadbeater , N. E. 2003 . Rapid, easy cyanation of aryl bromides and chlorides using nickel salts in conjuction with microwave promotion . J. Org. Chem. , 68 : 9122 – 9125 .
  • Qiong , Z. , Chi , H. , Guangyong , X. , Chongwen , X. and Yuanyin , C. 1999 . A direct synthesis of aromatic nitriles from methylaromatic compounds by ammoxidation on DC‐108 catalyst . Synth. Commun. , 29 : 2349 – 2353 .
  • Suzuki , N. , Kaneko , Y. , Nomoto , T. and Izawa , Y. 1984 . Synthetic reactions in polyethylene glycols: Diazotization and Sandmeyer reactions of anilines in polyethylene glycol–methylene dichloride . J. Chem. Soc., Chem. Commum. , 22 : 1523 – 1524 .
  • Hedberg , M. H. , Linnanen , T. , Jansen , J. M. , Nordvall , G. , Hjorth , S. , Unelius , L. and Johansson , A. M. 1996 . 11‐Substituted (R)‐aporphines: Synthesis, pharmacology, and modeling of D2A and 5HT1A receptor interaction . J. Med. Chem. , 39 : 3503 – 3513 .
  • Uozumi , Y. , Suzuki , N. , Ogiwara , A. and Hayashi , Y. 1994 . Preparation of optically active binaphthylmonophosphines (MOPs) containing various functional groups . Tetrahedron , 50 : 4293 – 4302 .
  • Kraus , G. A. and Maeda , H. 1994 . A direct preparation of 1,4‐benzodiazepines: The synthesis of medazepam and related compounds via a common intermediates . Tetrahedron Lett. , 35 : 9189 – 9190 .
  • Almansa , C. , Carceller , E. , Bartoroli , J. and Forn , J. 1993 . A short, efficient synthesis of 6‐cyano‐1‐tetralones . Synth. Commun. , 23 : 2965 – 2971 .
  • Takagi , K. , Sasaki , K. and Sakakibara , Y. 1991 . Nucleophilic displacement catalyzed by transition metal, IX: [Pd2(dba)3] · CHCl3 · DPPF catalyzed cyanation of aryl halides and aryl triflates . Bull. Chem. Soc. Jpn. , 64 : 1118 – 1121 .
  • Chambers , M. R. I. and Widdowson , D. A. 1989 . Nickel catalyzed conversion of phenol triflates into aromatic nitriles and acids . J. Chem. Soc., Perkin Trans. 1 , : 1365 – 1366 .
  • Takagi , K. and Sakakibara , Y. 1989 . Nickel(0) or palladium(0)‐catalyzed cyanation of aryl triflates . Chem. Lett. , : 1957 – 1958 .
  • Sundermeier , M. , Zapf , A. and Beller , M. 2003 . Palladium‐catalyzed cyanation of aryl halides: Recent developments and perspectives . Eur J. Inorg. Chem. , : 3513 – 3526 . For a recent review, see and references therein
  • Ellis , G. P. and Romney‐Alexander , T. M. 1987 . Cyanation of aromatic halides . Chem. Rev. , 87 : 779 – 794 .
  • Tschaen , D. M. , Desmond , R. , King , A. O. , Fortin , M. C. , Pipik , B. , King , S. and Verhoeven , T. R. 1994 . An improved procedure for aromatic cyanation . Synth. Commun. , 26 : 887 – 890 .
  • Zhang , A. and Neumeyer , J. L. 2003 . Microwave‐promoted Pd‐catalyzed cyanation of aryl triflates: A fast and versatile access to 3‐cyano‐3‐desoxy‐10‐ketomorphinans . Org. Lett. , 5 : 201 – 203 .
  • Kubota , H. and Rice , K. C. 1998 . Palladium‐catalyzed cyanation of hindered, electron‐rich aryl triflates by zinc cyanide . Tetrahedron Lett. , 39 : 2907 – 2910 .
  • Selnick , H. G. , Smith , G. R. and Tebben , A. J. 1995 . An improved procedure for the cyanation of aryl triflates: Convenient synthesis of 6‐cyanao‐1,2,3,4‐tetrahydro isoquinoline . Synth. Commun. , 25 : 3255 – 3261 .
  • Marcantonio , K. M. , Frey , L. F. , Liu , Y. , Chen , Y. , Sterine , J. , Phenix , B. , Wallace , D. J. and Chen , C.‐Y. 2004 . An investigation into causes and effects of high cyanide levels in the palladium‐catalyzed cyanation reaction . Org. Lett. , 6 : 3723 – 3725 .
  • Srivastava , R. R. and Collibee , S. E. 2004 . Application of polymer‐supported triphenylphosphine in the palladium‐catalyzed cyanation reaction under microwave conditions . Tetrahedron Lett. , 45 : 8895 – 8897 .

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