Polystyrene-Anchored Palladium(II) Schiff Base Complex: A Reusable Catalyst for Phosphine-Free and Copper-Free Sonogashira Cross-Coupling Reaction in Aqueous Medium

REFERENCES

• Tsuji , J. Palladium Reagents and Catalysts ; Wiley : Chichester: New York , 1995 .
   Google Scholar
• Malleron , J. L. ; Fiaud , J. C. ; Legros , J. Y. Handbook of Palladium-Catalyzed Organic Reactions ; Academic Press : London , 1997 .
   Google Scholar
• Diederich , F. ; Stang , P. J. Metal-Catalyzed Cross-coupling Reactions ; Wiley-VCH : Weinheim , 1999.
   Google Scholar
• Negishi , E. ; de Meijere , A. Handbook of Organopalladium Chemistry for Organic Synthesis ; Wiley-Interscience : New York , 2002 .
   Google Scholar
• Yin , L. ; Liebscher , J. Carbon–carbon coupling reactions catalyzed by heterogeneous palladium catalysts . Chem. Rev. 2007 , 107 , 133 – 173 .
   PubMed Web of Science ®Google Scholar
• Guan , J. T. ; Weng , T. Q. ; Yu , G. A. ; Liu , S. H. Copper-free PdCl2/PPh3-catalyzed Sonogashira coupling reaction of aryl bromides with terminal alkynes in water . Tetrahedron Lett. 2007 , 48 , 7129 – 7133 .
   Web of Science ®Google Scholar
• Bhattacharya , S. ; Sengupta , S. Palladium-catalyzed alkynylation of aryl halides (Sonogashira reaction) in water . Tetrahedron Lett. 2004 , 45 , 8733 – 8736 .
   Web of Science ®Google Scholar
• Bakherad , M. ; Keivanloo , A. ; Bahramian , B. ; Hashemi , M. Copper-free Sonogashira coupling reactions catalyzed by a water-soluble Pd–salen complex under aerobic conditions . Tetrahedron Lett. 2009 , 50 , 1557 – 1559 .
   Google Scholar
• Novak , Z. ; Szabo , A. ; Repasi , J. ; Kotschy , A. Sonogashira coupling of aryl halides catalyzed by palladium on charcoal . J. Org. Chem. 2003 , 68 , 3327 – 3329 .
   PubMedGoogle Scholar
• Polshettiwar , V. ; Len , C. ; Fihri , A. Silica-supported palladium: Sustainable catalysts for cross-coupling reactions . Coord. Chem. Rev. 2009 , 253 , 2599 – 2626 .
   Web of Science ®Google Scholar
• Kim , J. H. ; Lee , D. H. ; Jun , B. H. ; Lee , Y. S. Copper-free Sonogashira cross–coupling reaction catalyzed by polymer-supported N-heterocyclic carbene palladium complex . Tetrahedron Lett. 2007 , 48 , 7079 – 7084 .
   Google Scholar
• Djakovitch , L. ; Rollet , P. Sonogashira cross-coupling reactions catalysed by copper-free palladium zeolites . Adv. Synth. Catal. 2004 , 346 , 1782 – 1792 .
   Google Scholar
• Sonogashira , K. ; Tohda , Y. ; Hagihara , N. A convenient synthesis of acetylenes: Catalytic substitutions of acetylenic hydrogen with bromoalkenes, iodoarenes, and bromopyridines . Tetrahedron Lett. 1975 , 16 , 4467 – 4470 .
   Web of Science ®Google Scholar
• Sonogashira , K. ; Yatake , T. ; Tohda , Y. ; Takahashi , S. ; Hagihara , N. Novel preparation of σ-alkynyl complexes of transition metals by copper(I) iodide–catalysed dehydrohalogenation . J. Chem. Soc., Chem. Commun. 1977 , 291 – 292 .
   Google Scholar
• Takahashi , S. ; Kuroyama , Y. ; Sonogashira , K. ; Hagihara , N. A convenient synthesis of ethynylarenes and diethynylarenes . Synthesis 1980 , 627 – 630 .
   Google Scholar
• Siemsen , P. ; Livingston , R. C. ; Diederich , F. Acetylenic coupling: A powerful tool in molecular construction . Angew. Chem., Int. Ed. 2000 , 39 , 2632 – 2657 .
   PubMed Web of Science ®Google Scholar
• Chinchilla , R. ; Nájera , C. The Sonogashira reaction: A booming methodology in synthetic organic chemistry . Chem. Rev. 2007 , 107 , 874 – 922 .
   PubMed Web of Science ®Google Scholar
• Tykwinski , R. R. Evolution in the palladium-catalyzed cross-coupling of sp- and sp2-hybridized carbon atoms . Angew. Chem., Int. Ed. 2003 , 42 , 1566 – 1568 .
   PubMed Web of Science ®Google Scholar
• Negishi , E. ; Anastasia , L. Palladium-catalyzed alkynylation . Chem. Rev. 2003 , 103 , 1979 – 2017 .
   PubMed Web of Science ®Google Scholar
• Siemsen , P. ; Livingston , R. C. ; Diederich , F. Acetylenic coupling: A powerful tool in molecular construction . Angew. Chem., Int. Ed. Engl. 2000 , 39 , 2632 – 2657 .
   PubMed Web of Science ®Google Scholar
• Hay , A. S. Oxidative coupling of acetylenes, II . J. Org. Chem. 1962 , 27 , 3320 – 3321 .
   Web of Science ®Google Scholar
• Ye , Z. W. ; Yi , W. B. Polymer-supported palladium perfluorooctanesulfonate [Pd(OPf)2]: A recyclable and ligand-free palladium catalyst for copper-free Sonogashira coupling reaction in water under aerobic conditions . J. Fluorine Chem. 2008 , 129 , 1124 – 1128 .
   Web of Science ®Google Scholar
• Gil-Moltó , J. ; Karlström , S. ; Nájera , C. Di(2-pyridyl)methylamine–palladium dichloride complex covalently anchored to a styrene-maleic anhydride co-polymer as recoverable catalyst for C–C cross-coupling reactions in water . Tetrahedron 2005 , 61 , 12168 – 12176 .
   Google Scholar
• Liang , B. ; Huang , M.-W. ; You , Z.-J. ; Xiong , Z.-C. ; Lu , K. ; Fathi , R. ; Chen , J.-H. ; Yang , Z. Pd-catalyzed copper-free carbonylative Sonogashira reaction of aryl iodides with alkynes for the synthesis of alkynyl ketones and flavones by using water as a solvent. J. Org. Chem. 2005, 70, 6097–6100.
   PubMed Web of Science ®Google Scholar
• Thathagar , M. B. ; Rothenberg , G. One-pot Pd/C-catalyzed “domino” HALEX and Sonogashira reactions: A ligand- and Cu-free alternative . Org. Biomol. Chem. 2006 , 4 , 111 – 115 .
   Google Scholar
• Djakovitch , L. ; Rollet , P. Sonogashira cross-coupling reactions catalyzed by heterogeneous copper-free Pd-zeolites . Tetrahedron Lett. 2004 , 45 , 1367 – 1370 .
   Google Scholar
• Kim , J. H. ; Lee , D. H. ; Jun , B. H. ; Lee , Y. S. Copper-free Sonogashira cross–coupling reaction catalyzed by polymer-supported N-heterocyclic carbene palladium complex . Tetrahedron Lett. 2007 , 48 , 7079 – 7084 .
   Google Scholar
• Sotiriou-Leventis , C. ; Wang , X. ; Mulik , S. ; Thangavel , A. ; Leventis , N. Immobilization of Pd catalysts on mesoporous silica for amine- and copper-free Sonogashira coupling reactions . Synth. Commun. 2008 , 38 , 2285 – 2298 .
   Web of Science ®Google Scholar
• Onue , H. ; Moritani , I. Ortho-Metalation reactions of N-phenylbenzaldimine and its related compounds by palladium(II) acetate . J. Organomet. Chem. 1972 , 43 , 431 – 436 .
   Google Scholar
• Durig , J. R. ; Layton , R. ; Sink , D. W. ; Mitchell , B. R. Far infrared spectra of palladium compounds, I: The influence of ligands upon the palladium chloride stretching frequency . Spectrochim. Acta 1965 , 21 , 1367 – 1378 .
   Web of Science ®Google Scholar
• Islam , S. M. ; Mondal , P. ; Singha Roy , A. ; Mondal , S. ; Mobarak , M. An effcient and reusable polymer-supported palladium catalyst for the Suzuki cross-coupling reactions of aryl halides . J. Chem. Res. 2009 , 756 – 760 .
   Google Scholar
• Polshettiwar , V. ; Hesemann , P. ; Moreau , J. J. E. Palladium containing nanostructured silica functionalized with pyridine sites: A versatile heterogeneous catalyst for Heck, Sonogashira, and cyanation reactions . Tetrahedron 2007 , 63 , 9784 – 6790 .
   Google Scholar
• Komáromi , A. ; Novák , Z. Effcient copper-free Sonogashira coupling of aryl chlorides with palladium on charcoal . Chem. Commun. 2008 , 4968 – 4970 .
   Google Scholar
• Jana , S. ; Dutta , B. ; Bera , R. ; Konar , S. Imobilization of palladium in mesoporous silica matrix: Preparation, characterization, and its catalytic efficacy in carbon–carbon coupling reactions . Inorg. Chem. 2008 , 47 , 5512 .
   PubMed Web of Science ®Google Scholar
• Agawa , T. ; Miller , S. Reaction of silver acetylide with acylpyridinium salts: N–Benzoyl-2-phenylethynyl-1,2-dihydropyridine . J. Am. Chem. Soc. 1961 , 83 , 449 .
   Google Scholar
• Yanga , F. ; Cuia , X. ; Lia , Y. ; Zhanga , J. ; Rena , G. ; Wu , Y. Cyclopalladated ferrocenylimines: Efficient catalysts for homocoupling and Sonogashira reaction of terminal alkynes . Tetrahedron 2007 , 63 , 1963 .
   Google Scholar