Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 6
2,002
Views
8
CrossRef citations to date
0
Altmetric
Original Articles

Pd-Cu–Mediated Synthesis of 2-Substituted Imidazo[1,2-α]pyridines in Water

, &
Pages 1002-1011 | Received 09 Jul 2008, Published online: 25 Feb 2009

REFERENCES

  • (a) 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 ; (b) 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 , 9 , 291 ; (c) Takahashi , S. ; Kuroyama , Y. ; Sonogashira , K. ; Hagihara , N. A convenient synthesis of ethynylarenes and diethynylarenes . Synthesis . 1980 , 627 .
  • (a) Nicolaou , K. C. ; Dai , W. M. Chemistry and biology of the enediyne anticancer antibiotics . Angew. Chem., Int. Ed. Engl. 1991 , 30 , 1387 – 1416 ; (b) Paterson , I. ; Davies , R. D. M. ; Marquez , R. Total synthesis of the callipeltoside aglycon . Angew. Chem., Int. Ed. 2001 , 40 , 603 – 607 .
  • (a) Kort , M. ; Correa , V. ; Valentijn , A. R. P. M. ; Marel , G. A. ; Potter , B. V. L. ; Taylor , C. W. ; Boom , J. H. Synthesis of potent agonists of the D-myo-inositol 1,4,5-trisphosphate receptor based on clustered disaccharide polyphosphate analogues of adenophostin . A. J. Med. Chem. 2000 , 43 , 3295 – 3303 ; (b) Cosford , N. D. P. ; Tehrani , L. ; Roppe , J. ; Schweiger , E. ; Smith , N. D. ; Anderson , J. ; Bristow , L. ; Brodkin , J. ; Jiang , X. ; McDonald , I. ; Rao , S. ; Washburn , M. ; Varney , M. A. 3-[(2-Methyl-1,3-thiazol-4-yl)ethynyl]-pyridine: A potent and highly selective metabotropic glutamate subtype 5 receptor antagonist with anxiolytic activity . J. Med. Chem. 2003 , 46 , 204 – 206 .
  • (a) Brunsveld , L. ; Meijer , E. W. ; Prince , R. B. ; Moore , J. S. Self-assembly of folded m-phenylene ethynylene oligomers into helical columns. J. Am. Chem. Soc. 2001, 123, 7978–7984; (b) Mongin , O. ; Porres , L. ; Moreaux , L. ; Mertz , J. ; Blanchard-Desce , M. Synthesis and photophysical properties of new conjugated fluorophores designed for two-photon-excited fluorescence. Org. Lett. 2002, 4, 719–722.
  • (a) Mongin , O. ; Papamicaël , C. ; Hoyler , N. ; Gossauer , A. Modular synthesis of benzene-centered porphyrin trimers and a dendritic porphyrin hexamer . J. Org. Chem. 1998 , 63 , 5568 – 5580 ; (b) Tobe , Y. ; Utsumi , N. ; Nagano , A. ; Naemura , K. Synthesis and association behavior of [4.4.4.4.4.4]metacyclophanedodecayne derivatives with interior binding groups . Angew. Chem., Int. Ed. 1998 , 37 , 1285 – 1287 ; (c) Onitsuka , K. ; Fujimoto , M. ; Ohshiro , N. ; Takahashi , S. Convergent route to organometallic dendrimers composed of platinum-acetylide units . Angew. Chem., Int. Ed. 1999 , 38 , 689 – 692 .
  • (a) Genet , J. P. ; Blart , E. ; Savignac , M. Palladium-catalyzed cross-coupling reactions in a homogeneous aqueous medium . Synlett 1992 , 715 ; (b) 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 ; (c) Fukuyama , T. ; Shinmen , M. ; Nishitani , S. ; Sato , M. ; Ryu , I. A copper-free sonogashira coupling reaction in ionic liquids and its application to a microflow system for efficient catalyst recycling . Org. Lett. 2002 , 4 , 1691 – 1694 .
  • (a) 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 ; (b) 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 ; (c) Nakamura , K. ; Okubo , H. ; Yamaguchi , M. Low temperature Sonogashira coupling reaction . Synlett . 1999 , 549 ; (d) Choudary , B. M. ; Madhi , S. ; Chowdari , N. S. ; Kantam , M. L. ; Sreedhar , B. Layered double hydroxide supported nanopalladium catalyst for Heck-, Suzuki-, Sonogashira-, and Stille-type coupling reactions of chloroarenes . J. Am. Chem. Soc. 2002 , 124 , 14127 – 14136 ; (e) Köllhofer , A. ; Pullmann , T. ; Plenio , H. A versatile catalyst for the Sonogashira coupling of aryl chlorides . Angew. Chem., Int. Ed. 2003 , 42 , 1056 – 1058 ; (f) Faller , J. W. ; Kultyshev , R. G. ; Parr , J. Alkynyl germatranes as alternative reagents for the preparation of biarylethynes . Tetrahedron Lett. 2003 , 44 , 451 – 453 .
  • (a) Lubineau , A. ; Auge , J. In Modern Solvents in Organic Synthesis ; P. Knochel (Ed.); Springer : Berlin , 1999 ; (b) Cornils, B. Aqueous-Phase Organometallic Catalysis: Concepts and Applications; 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) Bhattacharya , S. ; Sengupta , S. Palladium catalyzed alkynylation of aryl halides (Sonogashira reaction) in water . Tetrahedron Lett. 2004 , 45 , 8733 – 8736 ; (g) López-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 ; (h) Raju , S. ; Mukkanti , K. ; Annamalai , P. ; Pal , M. Facile synthesis of substituted thiophenes via Pd/C-mediated sonogashira coupling in water . Bioorg. Med. Chem. Lett. 2006 , 16 , 6185 – 6189 .
  • (a) Heravi , M. M. ; Keivanloo , A. ; Rahimizadeh , M. ; Bakavoli , M. ; Ghassemzadeh , M. Pd–Cu catalyzed heterocyclization during Sonogashira coupling: Synthesis of 3-benzylthiazolo[3,2-a]benzimidazole . Tetrahedron Lett. 2004 , 45 , 5747 – 5749 ; (b) Heravi , M. M. ; Kivanloo , A. ; Rahimzadeh , M. ; Bakavoli , M. ; Ghassemzadeh , M. ; Neumüller , B. Regioselective synthesis of 6-benzylthiazolo-[3,2-b]1,2,4-triazoles during Sonogashira coupling . Tetrahedron Lett. 2005 , 46 , 1607 – 1610 ; (c) Heravi, M. M. ; Keivanloo, A. ; Rahimizadeh, M. ; Bakavoli, M. ; Ghassemzadeh, M. Synthesis of thiazolo[3,2-d][1,2,4] triazines through palladium-catalyzed heteroannulation of acetylenic compounds . J. Heterocycl. Chem. 2007 , 44 , 1 – 3 .
  • Bakherad , M. ; Isfahani , H. N. ; Keivanloo , A. ; Doostmohammadi , N. Pd-Cu catalyzed heterocyclization during Sonogashira coupling: Synthesis of 2-benzylimidazo[1,2-α]pyridine . Tetrahedron Lett. 2008 , 49 , 3819 – 3822 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.