A+Greener+Suzuki+Reaction

Hailey Baldwin

The Greener Suzuki Reaction Akira Suzuki originally published the Suzuki reaction in 1979. Suzuki received the 2010 Nobel Prize in Chemistry for the discovery and formation of the Suzuki reaction. This reaction is also known as Suzuki-Miyaura reaction and Suzuki Coupling. The fundamentals of the Suzuki reaction involve organometallic chemistry, which is the study of compounds containing bonds between carbon and metal. Lithium and Grignard reagents are a familiar example of organometallic chemistry. The general process of combining two separate hydrocarbon pieces with the help of a metal catalyst is called coupling. The significance of this coupling creates carbon-carbon bonds. The Suzuki reaction involves cross-coupling of two different chemical compounds versus the coupling of identical compounds known as homo-coupling. Aryl is any functional group substituent derived from a simple aromatic ring, this compound is one of the reactants in the Suzuki reaction the other reactant is a vinyl-halide, which is a vinyl groups with a formula of –CH=CH2 that contains a halide. Vinyl resembles the chemical formula of ethene, however a functional group replaces one of the hydrogen characterizing a vinyl. Palladium (0) complex is the metal catalyst that aids in binding of these two compounds. Palladium (0) complex must be made in situ from PdCl2 or Pd(OAc)2. Triphenylphosphine and palladium with a base and an isopropanol (aq) solvent can also be used.

Adaptation to the traditional Suzuki reaction are highlighted in “__Greening Up” the Suzuki Reaction__ by Evangelos Aktoudianakis, Elton Chan , Amanda R. Edward , Isabel Jarosz , Vicki Lee , Leo Mui , Sonya S. Thatipamala and Andrew P. Dicks Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada. The paper focuses on the synthetic formation of 4-phenylphenol in water. This experiment exchanges the isopropanol solvent for water and the in situ formation of palladium for palladium on carbon. This trade reduces the cost of the experiment and the hazardous. Water is free and much greener than the organic solvent that previously is used. This experiment is better for the environment and still provide the conditions that produce 4-phenylphenol. This biaryl compound is marketed as a non-steroidal anti-inflammatory drug.

** Methanol ** || ** 36.46 grams/mol ** ** 32.04 grams/mol ** || ** Add = pH below 7 ** || ** -98 ** ||
 * ** Compound ** || ** Molecular Weight in grams ** || ** Amount added ** || ** Melting point ** ||
 * ** Phenylboronic acid ** || ** 121.93 grams/mol ** || ** 122 mg or .122g ** || ** 216-219 ** ||
 * ** 4-iodophenol ** || ** 220.01 grams/mol ** || ** 220 mg or .220g ** || ** 92-94 ** ||
 * ** Potassium carbonate ** || ** 138.21 grams/mol ** || ** 415mg 0r .415g ** || ** 891 ** ||
 * ** 10% palladium on carbon ** || ** 106.42 grams/mol ** || ** 3mg ** ||  ||
 * ** 2 M HCL **

** Theoretical Mass yield = ** 1mmol of 4-phenylphenol 170.21mg or 0.17021g ** Atom economy ** =MW of desired product / MW of all reactants 4-Phenyl-phenol:170.21 g/mol / Phenylboronic acid: 121.93g/mol + 4-iodophenol: 220.01 g/mol + potassium carbonate 138.21 g/mol =.3544 x 100 = 35% I did not add in Palladium on carbon the catalysts. ** Effective Mass Yield %= ** mass of products x 100 / mass of non-benign reagents .17021g x 100 =17.021 / .003g 10% palladium on carbon + potassium carbonate .415g = 41%
 * Hazards (Sigma Aldrich website) **
 * Compounds || NFPAHealth || NFPA-Fire || NFPA-Reactive || Hazardous || Sigma-Aldrich # || Part in the reaction ||
 * Phenylboronic acid || 1 || 0 || 0 || Harmful if swallowed or inhaled, causes respiratory tract, eye and skin irritation || 78181 || reactant ||
 * 4-iodophenol || 3 || 0 || 0 || Toxic by ingestion – target organ is the thyroid, corrosive ||  || reactant ||
 * Potassium carbonate || 1 || 0 || 0 || Skin and eye irritation || P5833 || catalyst ||
 * Palladium on carbon || 0 || 0 || 0 || Harmful if swallowed || 205699 || catalyst ||
 * Hydrochloric acid || 3 || 0 || 1 || Burns and irritating to the respiratory tract || 320331 || used for acidification ||
 * Methanol || 2 || 3 || 0 || Highly flammable, toxic if swallowed or inhaled, irritates eyes, skin and respiratory tract || 322415 || recrystallization solvent mixture ||

carb carbon || Offer surplus and non-recyclable solutions to a licensed disposal company || *Although most organometallic reactions cannot be completed under aqueous conditions, the “greener Suzuki reaction” is possible. 50mL round-bottom flask Reflux equipment Vacuum filtration equipment Heat Sand bath Litmus paper IR spectroscope or Carbon NMR spectroscope
 * Compound Disposal Regulations (Sigma Aldrich website) **
 * Phenylboronic acid || Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material. ||
 * 4-iodophenol || Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. ||
 * Potassium carbonate || Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material. ||
 * Pal Palladium on
 * Hydrochloric acid || Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material ||
 * Methanol || Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material. ||
 * __ Equipment need for this experiment __**

Good job: I appreciate the background information you provide as well as the detail you have included about chemicals and hazards.