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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 7
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Original Articles

Synthesis of Poly-nitrile Aromatics via Palladium-Catalyzed Cyanation of Aryl Bromides with Potassium Hexacyanoferrate(II)

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Pages 1042-1051 | Received 03 Feb 2010, Published online: 03 Mar 2011

REFERENCES

  • (a) Larock , R. C. Comprehensive Organic Transformations ; VCH : New York , 1989 , p. 819 ; (b) Grundmann , C. Houben-Weyl: Methoden der organischen Chemie, , 4th ed. ; Vol. E5 ; J. Falbe ( Ed. ); Thieme : Stuttgart , 1985 ; p. 1313 .
  • Lindley , J. Copper assisted nucleophilic substitution of aryl halogen . Tetrahedron 1984 , 40 , 1433 .
  • Beletskaya , I. P. ; Sigeev , A. S. ; Peregudov , A. S. ; Petrovskii , P. V. Catalytic sandmeyer cyanation as a synthetic pathway to aryl nitriles . J. Organomet. Chem. 2004 , 689 , 3810 .
  • (a) Martin , A. ; Kalevaru , N. V. ; Lücke , B. ; Sans , M. Palladium-catalyzed cyanation of aryl halides . J. Green Chem. 2004 , 4 , 481 ; (b) Liu , Y. ; Zhong , M. ; Ma , Y. L. One-step synthesis of tolunitriles by heterogeneously catalyzed liquid-phase ammoxidation . Synth. Commun. 2005 , 35 , 2951 ; (c) Rombi , E. ; Ferino , I. ; Monaci , R. ; Picciau , C. ; Solinas , V. ; Buzzoni , R. Toluene ammoxidation on α-Fe2O3-based catalysts . Appl. Catal. A 2004 , 266 , 73 ; (d) Lücke , B. ; Narayana , K. V. ; Martin , A. ; Jähnisch , K. Oxidation and ammoxidation of aromatics . Adv. Synth. Catal. 2004 , 346 , 1407 .
  • Takagi , K. ; Okamoto , T. ; Sakakibara , Y. ; Oka , S. Palladium(II)-catalyzed synthesis of aryl cyanides from aryl halides . Chem. Lett. 1973 , 471 .
  • Pd-catalyzed cyanation of aryl halides: (a) Sekiya , A. ; Ishikawa , N. Facile synthesis of aryl cyanides from iodides catalyzed by palladium triphenylphosphine complex. Chem. Lett. 1975, 277; (b) Takagi , K. ; Okamoto , T. ; Sakakibara , Y. ; Ohno , A. ; Oka , S. ; Hayama , N. Nucleophilic displacement catalyzed by transition metal, I: General consideration of the cyanation of aryl halides catalyzed by palladium(II). Bull. Chem. Soc. Jpn. 1975, 48, 3298; (c) Takagi , K. ; Okamoto , T. ; Sakakibara , Y. ; Ohno , A. ; Oka , S. ; Hayama , N. Nucleophilic displacement catalyzed by transition metal, III: Kinetic investigation of the cyanation of iodobenzene catalyzed by palladium(II). Bull. Chem. Soc. Jpn. 1976, 49, 3177; (d) Dalton , J. R. ; Regen , S. L. Alumina assisted aryl cyanation. J. Org. Chem. 1979, 44, 4443; (e) Akita , Y. ; Shimazaki , M. ; Ohta , A. Einführung der Cyano-Gruppe in Pyrazine. Synthesis 1981, 974; (f) Chatani , N. ; Hanafusa , T. Transition-metal-catalyzed reactions of trimethylsilyl cyanide. 4: Palladium-catalyzed-cyanation of aryl halides by trimethylsilyl cyanide. J. Org. Chem. 1986, 51, 4714; (g) Takagi , K. ; Sasaki , K. ; Sakakibara , Y. Nucleophilic displacement catalyzed by transition metal. IX: [Pd2(dba)3] · CHCl3–DPPF catalyzed cyanation of aryl halides and aryl triflates. Bull. Chem. Soc. Jpn. 1991, 64, 1118; (i) Anderson , Y. ; Langström , B. Transition-metal-mediated reactions using [11C]cyanide in synthesis of 11C-labelled aromatic compounds. J. Chem. Soc., Perkin Trans. 1 1994, 1395; (j) Tschaen , D. M. ; Desmond , R. An improved procedure for aromatic cyanation. Synth. Commun. 1994, 24, 887; (k) Okano , T. ; Kiji , J. ; Toyooka , Y. Biphasic cyanation of aryl halides with counter phase transfer catalysts. Chem. Lett. 1998, 425; (l) Anderson , B. A. ; Bell , E. C. ; Ginah , F. O. ; Harn , N. K. ; Pagh , L. M. ; Wepsiec , J. P. Cooperative catalyst effects in palladium-mediated cyanation reactions of aryl halides and triflates. J. Org. Chem. 1998, 63, 8224; (m) Okano , T. ; Iwahara , M. Catalytic cyanation of aryl halides with NaCN in the presence of crowned phosphine complexes of palladium under solid-liquid two-phase conditions. Synlett 1998, 243; (n) Maligres , P. E. ; Waters , M. S. ; Fleitz , F. ; Askin , D. A highly catalytic robust palladium catalyzed cyanation of aryl bromides. Tetrahedron Lett. 1999, 40, 8193; (o) Jin , F. ; Confalone , P. N. Palladium-catalyzed cyanation reactions of aryl chlorides. Tetrahedron Lett. 2000, 41, 3271; (p) Sundermeier , M. ; Zapf , A. ; Beller , M. A new palladium catalyst system for the cyanation of aryl chlorides. Tetrahedron Lett. 2001, 42, 6707; (q) Jiang , B. ; Kan , Y. Synthesis of dialkyl cyanoboronates and their application in palladium-catalyzed cyanation of aryl halides. Tetrahedron. 2001, 57, 1581; (r) Sundermeier , M. ; Zapf , A. ; Beller , M. A convenient procedure for the palladium-catalyzed cyanation of aryl halides. Angew. Chem. Int. Ed. 2003, 42, 1661; (s) Chidambaram , R. A robust palladium-catalyzed cyanation procedure: beneficial effect of zinc acetate. Tetrahederon Lett. 2004, 45, 1441; (t) Hatsuda , M. ; Seki , M. A practical synthesis of highly functionalized aryl nitriles through cyanation of aryl bromides employing heterogeneous Pd/C. Tetrahedron Lett. 2005, 46, 1849; (u) Chobanian , H. R. ; Fors , B. A facile microwave-assisted palladium-catalyzed cyanation of aryl chlorides. Tetrahedron Lett. 2006, 47, 3303.
  • Schareina , T. ; Zapf , A. ; Beller , M. Potassium hexacyanoferrate(II)—A new cyanating agent for the palladium-catalyzed cyana-tion of aryl halides . Chem. Commun. 2004 , 1388 .
  • Schareina , T. ; Zapf , A. ; Beller , M. A new palladium catalyst system for the cyanation of aryl chlorides with K4[Fe(CN)6] . Tetrahedron Lett. 2007 , 48 , 1087 .
  • Schareina , T. ; Zapf , A. ; Beller , M. Improving palladium-catalyzed cyanation of aryl halides: Development of a state-of-the-art methodology using potassium hexacyanoferrate(II) as cyanating agent . J. Organomet. Chem. 2004 , 689 , 4576 .
  • Weissman , S. A. ; Zewge , D. ; Chen , C. Ligand-free palladium-catalyzed cyanation of aryl halides . J. Org. Chem. 2005 , 70 , 1508 .
  • Li , L. H. ; Pan , Z. L. ; Duan , X. H. ; Liang , Y. M. An environmentally benign procedure for the synthesis of aryl and arylvinyl nitriles assisted by microwave in ionic liquid . Synlett 2006 , 13 , 2094 .
  • Schareina , T. ; Zapf , A. ; Beller , M. An environmentally benign procedure for the Cu-catalyzed cyanation of aryl bromides . Tetrahedron Lett. 2005 , 46 , 2585 .
  • Schareina , T. ; Zapf , A. ; Mägerlein , W. ; Müller , N. ; Beller , M. A state-of-the-art cyanation of aryl bromides: A novel and versatile Copper catalyst system inspired by nature . Chem. Eur. J. 2007 , 13 , 6249 .
  • Kuester , F. ; Stallberg , A. Über einige Derivate des Mesitylens und die Verseifbarkeit aromatischer Säurenitrile . Justus Liebigs Ann. Chem. 1894 , 278 , 222 .
  • Sheldrick , G. M. SHELXS-97: Program for the Solution of Crystal Structures ; University of Göttingen; Göttingen : Germany , 1997 .

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