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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2009 - Issue 2
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Original Articles

Nickel-Catalyzed Alkynylation of Aryl Iodides (Sonogashira Reaction) in Water

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Pages 179-185 | Received 25 Aug 2008, Published online: 29 Dec 2009

REFERENCES

  • 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 .
  • Moore , J. S. Shape-persistent molecular architectures of nanoscale dimension . Acc. Chem. Res. 1997 , 30 , 402 – 413 .
  • 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 .
  • Negishi , E.-J. ; Anastasia , L. Palladium-catalyzed alkynylation . Chem. Rev. 2003 , 103 , 1979 – 2018 .
  • Chow , H.-F. ; Wan , C.-W. ; Low , K.-H. ; Yeung , Y.-Y. A highly selective synthesis of diarylethynes and their oligomers by a palladium-catalyzed Sonogashira coupling reaction under phase transfer conditions . J. Org. Chem. 2001 , 66 , 1910 – 1913 .
  • (a) Bong , D. T. ; Ghadiri , M. R. Chemoselective Pd(0)-catalyzed peptide coupling in water . Org. Lett. 2001 , 3 , 2509 – 2511 ; (b) Dibowski , H. ; Schmidtchen , F. P. Sonogashira cross-couplings using biocompatible conditions in water . Tetrahedron Lett. 1998 , 39 , 525 – 528 ; (c) Casalnuovo , A. L. ; Calabrese , J. C. Palladium-catalyzed alkylations in aqueous media . J. Am. Chem. Soc. 1990 , 112 , 4324 – 4330 .
  • Kabalka , G. W. ; Wang , L. ; Namboodiri , V. ; Pagni , R. M. Rapid microwave-enhanced, solventless Sonogashira coupling reaction on alumina . Tetrahedron Lett. 2000 , 41 , 5151 – 5154 .
  • (a) Nguefack , J.-F. ; Bolitt , V. ; Sinou , D. An efficient palladium-catalysed coupling of terminal alkynes with aryl halides under Jeffery's conditions . Tetrahedron Lett. 1996 , 37 , 5527 – 5530 ; (b) Buchmeiser , M. R. ; Schareina , T. ; Kempe , R. ; Wurst , K. Bis(pyrimidine)-based palladium catalysts: Synthesis, x-ray structure, and applications in Heck–, Suzuki–, Sonogashira–Hagihara couplings and amination reactions . J. Organomet. Chem. 2001 , 634 , 39 – 46 ; (c) Bohm , V. P. W. ; Herrmann , W. A. Coordination chemistry and mechanisms of metal-catalyzed C-C coupling reactions, 13: A copper-free procedure for the palladium-catalyzed Sonogashira reaction of aryl bromides with terminal alkynes at room temperature . Eur. J. Org. Chem. 2000 , 65 , 3679 – 3681 ; (d) Hundertmark , T. ; Littke , A. F. ; Buchwald , S. L. ; Fu , G. C. Pd(PhCN)2Cl2/P(t-Bu)3: A versatile catalyst for Sonogashira reactions of aryl bromides at room temperature . Org. Lett. 2000 , 2 , 1729 – 1731 ; (e) Netherton , M. R. ; Fu , G. C. Air-stable trialkylphosphonium salts: Simple, practical, and versatile replacements for air-sensitive trialkylphosphines: Applications in stoichiometric and catalytic processes . Org. Lett. 2001 , 3 , 4295 – 4297 .
  • (a) Crisp , G. T. ; Turner , P. D. ; Stephens , K. A. Palladium-catalysed coupling of terminal alkynes with aryl halides aided by catalytic zinc . J. Organomet. Chem. 1998 , 570 , 219 – 224 ; (b) Powell , N. A. ; Rychnovsky , S. D. Iodide acceleration in the Pd-catalyzed coupling of aromatic 1,2-ditriflates with alkynes: Synthesis of enediynes . Tetrahedron Lett. 1996 , 37 , 7901 – 7904 ; (c) Dai , W.-M. ; Guo , D.-S. ; Sun , L.-P. Chemistry of aminophenols, part 1: Remarkable additive effect on Sonogashira cross-coupling of 2-carboxamidoaryl triflates and application to novel synthesis of indoles . Tetrahedron Lett. 2001 , 42 , 5275 – 5278 .
  • (a) Thorand , S. ; Krause , N. Improved procedures for the palladium-catalyzed coupling of terminal alkynes with aryl bromides (Sonogashira coupling) . J. Org. Chem. 1998 , 63 , 8551 – 8553 ; (b) Alami , M. ; Ferri , F. ; Linstrumelle , G. An efficient palladium-catalysed reaction of vinyl and aryl halides or triflates with terminal alkynes . Tetrahedron Lett. 1993 , 34 , 6403 – 6406 ; (c) Alami , M. ; Crousse , B. ; Ferri , F. Weakly ligated palladium complexes PdCl2(RCN)2 in piperidine: Versatile catalysts for Sonogashira reaction of vinyl chlorides at room temperature . J. Organomet. Chem. 2001 , 624 , 114 – 123 .
  • Biffis , A. ; Scattolin , E. ; Ravasio , N. ; Zaccheria , F. Supported copper precatalysts for ligand-free, palladium-free Sonogashira coupling reactions . Tetrahedron Lett. 2007 , 48 , 8761 – 8764 .
  • (a) Lubineau , A. ; Auge , J. In Modern Solvents in Organic Synthesis ; P. Knochel (Ed.); Springer : Berlin , 1999 ; (b) Organic Synthesis in Water ; P. A. Grieco (Ed.); Blackie Academic & Professional : London , 1998 ; (c) Aqueous-Phase Organometallic Catalysis: Concepts and Applications ; B. Cornils and W. A. Herrmann (Eds.); Wiley-VCH : Weinheim , 1998 .
  • (a) Casalnuovo , A. L. ; Calabrese , J. C. Palladium-catalyzed alkylations in aqueous media . J. Am. Chem. Soc. 1990 , 112 , 4324 – 4330 ; (b) DeVasher , R. B. ; Moore , L. R. ; Shaughnessy , K. H. Aqueous-phase, palladium-catalyzed cross-coupling of aryl bromides under mild conditions, using water-soluble, sterically demanding alkylphosphines . J. Org. Chem. 2004 , 69 , 7919 – 7927 ; (c) Anderson , K. W. ; Buchwald , S. L. General catalysts for the Suzuki–Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water . Angew. Chem. Int. Ed. 2005 , 44 , 6173 – 6177 ; (d) Mio , M. J. ; Kopel , L. C. ; Braun , J. B. ; Gadzikwa , T. L. ; Hull , K. L. ; Brisbois , R. G. ; Markworth , C. J. ; Grieco , P. A. One-pot synthesis of symmetrical and unsymmetrical bisarylethynes by a modification of the Sonogashira coupling reaction . Org. Lett. 2002 , 4 , 3199 – 3202 ; (e) Bumagin , N. A. ; Sukhomlinova , L. I. ; Luzikova , E. V. ; Tolstaya , T. P. ; Beletskaya , I. P. Catalytic coupling of terminal acetylenes with iodoarenes and diaryliodonium salts in water . Tetrahedron Lett. 1996 , 37 , 897 – 900 ; (f) Lo'pez-Deber , M. P. ; Castedo , L. ; Granja , J. R. Synthesis of N-(3-arylpropyl)amino acid derivatives by Sonogashira types of reaction in aqueous media . Org. Lett. 2001 , 3 , 2823 – 2826 ; (g) Appukkuttan , P. ; Dehaen , W. ; Van der Eycken , E. Transition-metal-free Sonogashira-type coupling reactions in water . Eur. J. Org. Chem. 2003 , 68 , 4713 – 4716 .
  • Liang , B. ; Dai , M. ; Chen , J. ; Yang , Z. Copper-free Sonogashira coupling reaction with PdCl2 in water under aerobic conditions. J. Org. Chem. 2005, 70, 391–393.
  • Carpino , L. A. ; Chen , H. W. Diphenylthiirene 1-oxide: Synthesis, characterization, and reactivity . J. Am. Chem. Soc. 1979 , 101 , 390 – 394 .
  • Kabalka , G. W. ; Wang , L. ; Pagni , R. M. Sonogashira coupling and cyclization reactions on alumina: A route to aryl alkynes, 2-substituted-benzo[b]-furans, and 2-substituted-indoles . Tetrahedron 2001 , 57 , 8017 – 8028 .
  • Cai , M. ; Sha , J. ; Xu , Q. MCM-41-supported bidentate phosphine palladium(0) complex: A highly active and recyclable catalyst for the Sonogashira reaction of aryl iodides . Tetrahedron 2007 , 63 , 4642 – 4647 .
  • Cai , M. ; Zhou , Z. ; Jiang , J. A facile stereoselective synthesis of (2E)-3-silylallylic alcohols by hydromagnesiation of 1-aryl-2-silylacetylenes . Eur. J. Org. Chem. 2006 , 6 , 1400 – 1402 .

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