246
Views
6
CrossRef citations to date
0
Altmetric
Original Articles

Interrogation of a Sonogashira Cross-Coupling of 8-Bromoguanosine with Phenylacetylene on Amberlite: Evidence for Pd/Cu Ion Binding and Propagation of Pd/Cu Nanoparticles

, , &
Pages 168-184 | Received 07 Nov 2010, Accepted 14 Dec 2010, Published online: 24 Feb 2011

REFERENCES

  • Negishi , E . 2002 . Handbook of Organopalladium Chemistry for Organic Synthesis , New York : Wiley InterScience . vol. 1
  • Heck , R. F. 1985 . Palladium Reagents in Organic Syntheses , New York : Academic Press .
  • Tsuji , J. 1995 . Palladium Reagents and Catalysts , Chichester : Wiley .
  • Sonogashira , K. 2002 . Development of Pd-Cu catalyzed cross-coupling of terminal acetylenes with sp2-carbon halides . J. Organomet. Chem. , 653 : 46 – 49 .
  • Chinchilla , R. and Nájera , C. 2007 . The Sonogashira reaction: a booming methodology in synthetic organic chemistry . Chem. Rev. , 107 : 874 – 922 .
  • Nicolaou , K. C. , Bulger , P. G. and Sarlah , D. 2005 . Palladium-catalyzed cross-coupling reactions in total synthesis . Angew. Chem., Int. Ed. , 44 : 4442 – 4489 .
  • Itami , K. and Yoshida , J. 2006 . Multisubstituted olefins: platform synthesis and applications to materials science and pharmaceutical chemistry . Bull. Chem. Soc. Jap. , 79 : 811 – 824 .
  • Collings , J. C. , Parsons , A. C. , Porrès , L. , Beeby , A. , Batsanov , A. S. , Howard , J. A.K. , Lydon , D. P. , Low , P. J. , Fairlamb , I. J.S. and Marder , T. B. 2005 . Optical properties of donor-acceptor phenylene-ethynylene systems containing the 6-methylpyran-2-one group as an acceptor . Chem. Commun. , : 2666 – 2668 .
  • Zhang , X. , Bernet , B. and Vasella , A. 2007 . Oligonucleotide analogues with integrated bases and backbone Part 14: synthesis and association of ethynylene-linked self-complementary tetramers . Helv. Chim. Acta , 90 : 792 – 819; .
  • Seela , F. and Zulauf , M. 1998 . Synthesis of 7-alkynylated 8-aza-7-deaza-2′-deoxyadenosines via the Pd-catalysed cross-coupling reaction . J. Chem. Soc., Perkin Trans. 1 , : 3233 – 3239; .
  • Seela , F. and Zulauf , M. Palladium-catalyzed cross-coupling of 7-iodo-2′-deoxytubercidin with terminal alkynes . Synthesis , 1996 726 – 730 .
  • Carey , J. S. , Laffan , D. , Thomson , C. and Williams , M. T. 2006 . Analysis of the reactions used for the preparation of drug candidate molecules . Org. Biomol. Chem. , 4 : 2337 – 2347 .
  • Garg , N. K. , Woodroofe , C. C. , Lacenere , C. J. , Quake , S. R. and Stoltz , B. M. 2005 . A ligand-free solid-supported system for Sonogashira couplings: applications in nucleoside chemistry . Chem. Commun. , : 4551 – 4553 .
  • Yin , L. and Liebscher , J. 2007 . Carbon-carbon coupling reactions catalyzed by heterogeneous palladium catalysts . Chem. Rev. , 107 : 133 – 173 .
  • The use of unprotected nucleosides in cross-coupling reactions remains relatively rare, see , Crisp , G. T. and Gore , J. 1997 . Palladium-catalysed attachment of labels with acetylenic linker arms to biological molecules . Tetrahedron , 53 : 1523 – 1544 . reference 12. For a general review on the Pd-catalyzed reactions of nucleosides, see: Agrofoglio, L. A.; Gillaizeau, I.; Saito, Y. Palladium-assisted routes to nucleosides. Chem. Rev. 2003, 103, 1875–1916; see also Thoresen, L.H.; Jiao, G.-S.; Haaland, W.C.; Metzker, M.L.; Burgess, K. Rigid, conjugated, fluoresceinated thymidine triphosphates. Chem. Eur. J. 2003, 9, 4603–4610
  • Halogenated guanosines contain a labile ribose motif possessing secondary and primary hydroxyl moieties capable of binding metal ions. In addition, the purine moiety can participate in metal binding via several coordination modes .
  • Firth , A. G. , Fairlamb , I. J.S. , Darley , K. and Baumann , C. G. 2006 . Sonogashira alkynylation of unprotected 8-brominated adenosines and guanosines: Fluorescence properties of compact conjugated acetylenes containing a purine ring . Tetrahedron Lett. , 47 : 3529 – 3533 . Very recently, an elegant method for the 8-alkynylation of 8-bromo-2′-deoxyguanosine was reported by the Shaughnessy group, see: Cho, J.H.; Prickett, C.D.; Shaughnessy, K.H. Efficient Sonogashira coupling of unprotected halonucleosides in aq ueous solvents using water-soluble palladium catalysts. Eur. J. Org. Chem. 2010, 3678–3683
  • Pneumatikakis , G. 1984 . 1:1 Complexes of palladium(II) and platinum(II) with caffeine and their interaction with nucleosides . Inorg. Chim. Acta , 93 : 5 – 11; .
  • Dehand , J. and Jordanov , J. Interaction of cis-diaminotolueneplatinum(II) with nucleosides: evidence for guanosine O(6).N(7) chelation by platinum . J. Chem. Soc. Chem. Commun. , 1976 598 – 599 .
  • Western , E. C. and Shaughnessy , K. H. 2005 . Inhibitory effects of the guanine moiety on the Suzuki couplings of unprotected halonucleosides in aqueous media . J. Org. Chem. , 70 : 6378 – 6388 . Studies by Wagner have demonstrated that it is possible to conduct Suzuki-Miyaura cross-couplings on phosphorylated nucleosides in aqueous media using a solubilising phosphine ligand, see: Collier, A.; Wagner, G. A facile two-step synthesis of 8-arylated guanosine mono- and triphosphates (8-aryl GXPs). Org. Biomol. Chem. 2006, 4, 4526–4532
  • XPS has been used extensively to study palladium nanoparticles (heterogenized species) in various applications (including cross-coupling processes). For selected references, see , Lengke , M. F. , Fleet , M. E. and Southam , G. 2007 . Synthesis of palladium nanoparticles by reaction of filamentous cyanobacterial biomass with a palladium(II) chloride complex . Langmuir , 23 : 8982 – 8987 . and references cited therein
  • Amberlite IRA-67 (CAS no. 80747–90-6) was purchased from Sigma-Aldrich (Acrylaic (gel) matrix; 16–50 mesh; 1.6 meq(mL exchange capacity; ∼60% moisture) .
  • Cai , C. and Vasella , A. 1995 . Oligosaccharide analogues of polysaccharides. Part 5. Studies on the cross-coupling of alkynes and haloalkynes . Helv. Chim. Acta , 78 : 2053 – 2064 . and references cited therein
  • Amatore , C. and Jutand , A. 1998 . Role of dba in the reactivity of palladium(0) complexes generated in situ from mixtures of Pd(dba)2 and phosphines . Coord. Chem. Rev. , 180 : 511 – 528 .
  • Berg , J. M. and Holm , R. H. 1985 . Model for the active sites of oxo-transfer molybdoenzymes: reactivity, kinetics, and catalysis . J. Am. Chem. Soc. , 107 : 925 – 932 .
  • Canty , A. J. and Tobias , R. S. 1979 . Heavy metal nucleoside interactions . Inorg. Chem. , 18 : 413 – 417 .
  • Lee , T.-J. , Chun , B. C. and Chung , Y.-C. 2003 . Detoxification of reactive compounds by a cyclic electrolytic system with surface-modified ion-exchange resin . React. Funct. Poly. , 56 : 37 – 44 .
  • Reetz , M. T. and de Vries , J. G. 2004 . Ligand-free Heck reactions using low Pd-loading . Chem. Commun. , : 1559 – 1563 .
  • The application of recoverable nanosized palladium(0) catalysts (∼7 nm) on polyvinylpyrrolidinone (PVP) has been reported for the Sonogashira alkynylation reaction , Li , P. , Wang , L. and Lia , H. 2005 . Application of recoverable nanosized palladium(0) catalyst in Sonogashira reaction . Tetrahedron , 61 : 8633 – 8640 .
  • For an original report on the use of Pd(PVP nanoparticles in cross-coupling processes , Bradley , J. S. , Millar , J. M. and Hill , E. W. 1991 . Surface chemistry on colloidal metals: A high-resolution nuclear magnetic resonance study of carbon monoxide adsorbed on metallic palladium crystallites in colloidal suspension . J. Am. Chem. Soc. , 113 : 4016 – 4017 . For another important application, see:
  • Ellis , P. E. , Fairlamb , I. J.S. , Hackett , S. F.J. , Wilson , K. and Lee , A. F. 2010 . Evidence for the surface catalysed Suzuki-Miyaura reaction over Pd nanoparticles: an operando XAS study. Angew . Chem. Int. Ed. , 49 : 1820 – 1824 .
  • Broadwater , S. J. and McQuade , D. T. 2006 . Investigating PdEnCat catalysis . J. Org. Chem. , 71 : 2131 – 2134; .
  • Choudary , B. M. , Madhi , S. , Chowdari , N. S. , Kantam , M. L. and Sreedhar , B. 2002 . Layered double hydroxide supported nanopalladium catalyst for Heck-, Suzuki-, Sonogashira-, and Stille-Type coupling reactions of chloroarenes . J. Am. Chem. Soc. , 124 : 14127 – 14136 .
  • Gaikwad , A. V. , Holuigue , A. , Thathagar , M. B. , ten Elshof , J. E. and Rothenberg , G. 2007 . Ion-leaching and atom-leaching mechanisms from palladium nanoparticles in cross-coupling reactions . Chem. Eur. J. , 13 : 6908 – 6913 . It is acknowledged that the initial oxidative addition reaction with the organohalide could occur on the metal surface, for example, defect site, of the palladium nanoparticle (cluster), before being released into solution to participate in a “homogenous” reaction. For an excellent comprehensive discussion of this important aspect in the Heck reaction, see:
  • Köhler , K. , Kleist , W. and Pröckl , S. S. 2007 . Genesis of coordinatively unsaturated palladium complexes dissolved from solid precursors during Heck coupling reactions and their role as catalytically active species . Inorg. Chem. , 46 : 1876 – 1883 .
  • Ropartz , L. , Meeuwenoord , N. J. , Van Der Marel , G. A. , van Leeuwen , P. W.N.M. , Slawina , A. M.Z. and Kamer , P. C.J. 2007 . Phosphine containing oligonucleotides for the development of metallodeoxyribozymes . Chem. Commun. , : 1556 – 1558 .
  • Sheu , C. and Foote , C. S. 1995 . Reactivity toward singlet oxygen of a 7,8-dihydro-8-oxoguanosine(“8-hydroxyguanosine”) formed by photooxidation of a guanosine derivative . J. Am. Chem. Soc. , 117 : 6439 – 6442 .

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.