SYNTHESIS AND CHARACTERISATION OF PALLADIUM CATALYSED (CARBON-CARBON) BOND FORMATION COMPOUNDS

GUIDED BYMr. SUNIL JAWLA (Assistant Professor)

PRESENTED BYNAMITA JOSHI (Roll No-1117057505)

Typical palladium catalysts used include the following compounds:  tetrakis(triphenylphosphine)palladium(0)  bis(triphenylphosphine)palladium(II) dichloride . Examples include:  Heck reaction between alkenes and aryl halides  Suzuki reaction between aryl halides and boronic acids  Stille reaction between organohalides and organotin compounds  Hiyama coupling between organohalides and organosilicon compounds  Sonogashira coupling between aryl halides and alkynes.INTRODUCTION Palladium complex are used as a catalyst in many coupling reactions. with copper(I) iodide as a co-catalyst  Negishi coupling between an organohalide and an organozinc compound.

the Suzuki reaction couples boronic acids (containing an organic substituent) to halides.SUZUKI REACTION  First published in 1979 by Akira Suzuki.  The Relative reactivity: R2-I > R2-OTf > R2-Br >> R2-Cl .

.  For the synthesis of crizotinib (synthetic product that is highly active against lung carcinoma).SCOPE  For synthesis of complex compounds.  Has been used on a citronellal derivative for the synthesis of caparratriene (highly active against leukemia).

 In chemical and pharmaceutical industries. .  widespread use in organic synthetic applications is due to the mild conditions associated with the reactions together with their tolerance of a wide range of functional groups.APPLICATIONS  Has a large impact on synthetic organic chemistry and have found many applications in target oriented synthesis.  Applied in the synthesis of a large number of natural products and biologically active compounds of complex molecular structures.

MECHANISM .

HECK REACTION KUMADA COUPLING HIYAMA COUPLING NEGISHI COUPLING .

. and vinyl. STILLE REACTION The Stille reaction (also known as Stille Coupling) is a chemical reaction coupling an organotin compound with an sp2-hybridized organic halide catalyzed by palladium. aldehyde.or arylboronic acid to form substituted amines. The reaction is widely used in organic synthesis.PETASIS REACTION The Petasis reaction (alternatively called Petasis borono-Mannich (PBM) Reaction) is the chemical reaction of an amine.

 Synthesis of bi phenyl Compounds.  Column chromatography  TLC Screening.METHODOLOGY  Collection of raw material.  Confirmed by Nuclear magnetic resonance spectroscopy and Mass Spectroscopy. .

 Characterization of compounds by NMR and Mass spectroscopy. .PLAN OF WORK  Procurement of Raw Material.  Literature Review.  Isolation of compounds by column chromatography.  Proposed scheme.

and the Stille reaction —three versatile methods for the introduction of new C—C bonds on solid support.Powers et al(2011). the Heck.Pd-catalyzed cross-coupling reactions of alkyl halides.  David C.Pd(II)-Catalyzed C–H Activation/C–C CrossCoupling Reactions: Versatility and Practicality.  Newman SG et al(2011).Palladium-catalyzed carboiodination of alkenes: carbon-carbon bond formation with retention of reactive functionality .The Suzuki.Palladium(III) in Synthesis and Catalysis  Xiao Chen et al(2010).LITERATURE REVIEW  Robert Franzen et al(2000).  Kambe n et al(2011).

copper(I)mediated coupling of boronic acids with cyclic thioamides. Palladium-catalyzed carbon-carbon bond formation and cleavage of organo(hydro)fullerenes.and alkenylboronic acids. .. selective carbon-carbon bond formation for the functionalization of heterocycles.  Martin R et al (2008).  Prokopkova H et al (2007). Palladium-catalyzed Suzuki-Miyaura crosscoupling reactions employing dialkylbiaryl phosphine ligands. Palladium(0)-catalyzed.  Tsukamoto H et al (2008).LITERATURE REVIEW contd. Palladium(0)-catalyzed direct crosscoupling reaction of allylic alcohols with aryl.  Nambo M et al (2009).

org  http://www.organic-chemistry.com  http://www.pubmed.springerlink.interscience.sciencedirect.bioline.com  http://www.com  http://www.com  http://www.org .WEBSITE/ADDRESSED  http://www.wiley.

-T. M. Rev. The Heck reaction in the production of fine chemicals. and Vickers.. Luke. D. Chang. A. Chem. (2001). and Muhuhi. Soc. 1086. . E. C.and Tin-Based Methods. V. Hughes. (2000).(2009). Palladium-Catalyzed Cross-Coupling Reactions of Organosilanols and Their Salts: Practical Alternatives to Boron. P. R. S. R. Canadian Journal of Chemistry. C.. and Regens. The Heck Reaction as a Sharpening Stone of Palladium Catalysis. R.. 3009–3066.. E. M. J. J. G. M. Perkin Trans. Accounts of Chemical Research.: 2982. S. I. L. W. S. Journal of the American Chemical Society 131: 3104. (2008). T. 1486. and Cheprakov.  Beletskaya.BIBLOGRAPHY. J.S.  Denmark. Harwood. Smith.. Cross- Coupling Reactions of Aromatic and Heteroaromatic Silanolates with Aromatic and Heteroaromatic Halides. G.  Currie. Drew. (2000).. J. B. Chem.  De Vriesand Johannes G. W.  Denmark. A.

L. S. J.M. R. "Cross-Coupling Reactions of Aromatic and Heteroaromatic Silanolates with Aromatic and Heteroaromatic Halides".-T.. Drew.. . R.: 1953. M..  Harwood. S. Luke. 42: 2545. Pearson education. Upper Saddle River.W. Chem. C. B. Tetrahedron Lett. G. et al (2001).. Commun..K. W. E.New Jersey.. Muhuhi. Journal of the American Chemical Society 131: 3104. Tarr DA. et al (2009). et al (1996). K. Chang. B. Trotter. et al (2004) Inorganic chemistry. Smith. M.  Miessler GL.. Denmark. W.  Nanda.3457. A. G. Currie.. T.

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