Suzuki RXN lab Report(lame)

Suzuki RXN lab Report(lame) - Nafe Qureshi Suzuki Cross...

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Nafe Qureshi 11/02/08 Suzuki Cross Coupling Lab Report CHE 301 Abstract The Suzuki reaction is a synthesis method between an aromatic Boronic acid and a halogenated alkyl compound that is widely used in industry due to its wide applicability and easily available and disposed of reagents. It is a metal catalyzed reaction using nickel or palladium in an oxidized state as the active catalyst. A particular instance of this synthetic method was performed to couple two aryl compounds, namely Phenyl-Boronic acid and Para-Bromo Phenol to yield an intermediate biaryl product Para-Phenyl- Acetophenone. This product was further reduced using Sodium Borohydride to yield the final product, 1-(2-OH-Ethyl)-4-Phenyl-Benzene. I ntroduction The fusion of two Aromatic rings is a very useful synthetic reaction for Organic chemists. In medicinal chemistry many structural backbones of important drugs are linked aromatic compounds. The Suzuki reaction uses a 5 step reaction mechanism with Pd in its 0 oxidation state as the catalyst. Most important 3 mechanism in this reaction are following. i. Oxidative Addition ii. Transmetalation iii. Reductive Elimination In brief, Suzuki_miyura can be said to be a cross-coupling reaction consisting a catalytic cycle of mechanisms above.
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Reaction and Mechanism Part A Oxidative Addition: In the first step of this particular instance of a Suzuki coupling, 4-Bromo-Acetophenone is used as the starting material which is reacted with Pd(PPh3)2. This reduced form of Pd has the effect of nucleophilicaly attacking the aromatic ring at the position of the bound Br. This produces 4-Pd(PPh3)2Br- Acetophenone. In the second step of the reaction, Phenyl Boronic acid is reacted with Bi-Sodium Carbonate to yield a Phenyl Boronic acid Carbonate ion. In the reaction (CO3)2- acts as the nucleophile to the electron deficient boron atom.
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: In the third step of the reaction, the products from step one and two react with each other in an elimination reaction to afford the bi-ligated product 4- Pd(PPh3)2Ar-Acetophenone. Sodium Bromo-Boronic-Carbonate is the byproduct of this reaction. This reaction likely occurs due to the Pd atoms greater ability to stabilize the resonance characteristics of the benzene ring and the greater affinity of boron for the ionic bromine. In the forth step the di-ligated Pd (PPh3)2 undergoes a simple rearrangement to
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This note was uploaded on 11/10/2010 for the course CHE Intermedia taught by Professor Dr.richard during the Spring '10 term at SUNY Buffalo.

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Suzuki RXN lab Report(lame) - Nafe Qureshi Suzuki Cross...

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