Suzuki Palladium Cross-Coupling Reaction: Synthesis of 4-Acetyl-4-Methyldiphenyl

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Athena Cochinamogulos Dr. Miller Organic Chemistry II October 23, 13 Title: Suzuki Palladium Cross-Coupling Reaction: Synthesis of 4-Acetyl-4-methyldiphenyl Abstract: In this experiment, the Suzuki Cross coupling reaction between 4-methylphenylboronic acid and 4-bromoacetophenone was utilized to prepare 1-(4’methyl-biphenyl-4-yl) ethanone. Purification through vacuum filtration was carried out and rotary evaporation was executed. The characterization of the purified product was determined by comparing its spectra and melting points to those presented in the literature. The melting point of the product was 58-70°C; which largely differs from the literature value suggesting impurities but the use of spectra data allowed for the determination of product and overall experimental successful. Reaction Equation: Introduction: An organic reaction of an aryl- or vinyl-boronic acid with an aryl- or vinyl-halide catalyzed by a palladium (0) complex or by a palladium nanomaterial-based catalyst describes the Suzuki reaction first reported by Miyaura, Yanagi, and Suzuki in 1981. This reaction is an efficient methodology for the synthesis of sp2-sp2 carbon-carbon bonds. The Suzuki reaction is widely used to synthesize poly-olefins, styrenes, and substituted-biphenyls, and has been extended to incorporate alkyl bromides. The overall purpose of this experiment was to understand the requirements needed to facilitate a Suzuki cross-coupling reaction. In this reaction, the palladium reagent underwent oxidative addition where it gave up two electrons in order to bond to carbon and halogen during the formation and isomerization of a cis-organopalladium complex to the trans complex. Transmetallation followed this mechanistic step and consisted of the transfer of ligands from one metal to another through the addition of an R-M compound, 4-methylphenylboronic

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