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

GUIDED BYMr. SUNIL JAWLA (Assistant Professor)

PRESENTED BYNAMITA JOSHI (Roll No-1117057505)

INTRODUCTION
Palladium complex are used as a catalyst in many coupling reactions. 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, with copper(I)

iodide as a co-catalyst Negishi coupling between an organohalide and an organozinc compound. Typical palladium catalysts used include the following compounds: tetrakis(triphenylphosphine)palladium(0) bis(triphenylphosphine)palladium(II) dichloride

SUZUKI REACTION
First published in 1979 by Akira Suzuki, the Suzuki

reaction couples boronic acids (containing an organic substituent) to halides. The Relative reactivity: R2-I > R2-OTf > R2-Br >> R2-Cl

SCOPE
For synthesis of complex compounds.
Has been used on a citronellal derivative for the synthesis

of caparratriene (highly active against leukemia). For the synthesis of crizotinib (synthetic product that is highly active against lung carcinoma).

APPLICATIONS
Has a large impact on synthetic organic chemistry and

have found many applications in target oriented synthesis. 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. Applied in the synthesis of a large number of natural products and biologically active compounds of complex molecular structures. In chemical and pharmaceutical industries.

MECHANISM

HECK REACTION

KUMADA COUPLING

HIYAMA COUPLING

NEGISHI COUPLING

PETASIS REACTION
The Petasis reaction (alternatively called Petasis borono-Mannich (PBM) Reaction) is the chemical reaction of an amine, aldehyde, and vinyl- or arylboronic acid to form substituted amines.

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. The reaction is widely used in organic synthesis.

METHODOLOGY
Collection of raw material.
Synthesis of bi phenyl Compounds. Column chromatography

TLC Screening.
Confirmed by Nuclear magnetic resonance spectroscopy

and Mass Spectroscopy.

PLAN OF WORK
Procurement of Raw Material. Literature Review. Proposed scheme.

Isolation of compounds by column chromatography. Characterization of compounds by NMR and Mass

spectroscopy.

LITERATURE REVIEW
Robert Franzen et al(2000);The Suzuki, the Heck, and the Stille

reaction three versatile methods for the introduction of new CC bonds on solid support. David C.Powers et al(2011);Palladium(III) in Synthesis and Catalysis Xiao Chen et al(2010);Pd(II)-Catalyzed CH Activation/CC CrossCoupling Reactions: Versatility and Practicality. Kambe n et al(2011);Pd-catalyzed cross-coupling reactions of

alkyl halides.
Newman SG et al(2011);Palladium-catalyzed carboiodination of

alkenes: carbon-carbon bond formation with retention of reactive functionality

LITERATURE REVIEW contd..

Nambo M et al (2009); Palladium-catalyzed carbon-carbon bond

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

WEBSITE/ADDRESSED
http://www.sciencedirect.com
http://www.interscience.wiley.com http://www.springerlink.com

http://www.bioline.org
http://www.pubmed.com http://www.organic-chemistry.org

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