Contact Information

Author
  • Andy Dicks
  • Senior Lecturer
  • Chemistry
  • Univ. of Toronto
  • 80 St. George Street
  • Toronto, ON
  • M5S 3H6
  • Canada
Email
Phone
(416) 946 - 8003
Website

"Greening Up" the Suzuki Reaction

Author Contact: adicks@chem.utoronto.ca

Summary

An aqueous Suzuki reaction is described which highlights the facile preparation of a non-steroidal anti-inflammatory (NSAID) drug analog under green conditions. While palladium catalyzed cross-coupling reactions are common in most modern organic chemistry labs, they are often performed with hazardous solvents and large amounts of corrosive additives. Undertaken at the mid-undergraduate level, students use environmentally benign potassium carbonate as a base in water to generate a biaryl product.

This approach eliminates use of organic solvents in the synthesis and employs an alcohol/water mixture for purification. An additional feature is the 30-minute reaction time leading to reduced energy consumption compared with traditional Suzuki protocols. This approach introduces students to an industrially important reaction while also providing a platform for introducing or reinforcing the principles of green chemistry.

Supplemental materials include notes for the instructor (equipment needs, CAS numbers, synthetic notes, etc.), laboratory notes for the students (experimental procedure, background info, etc.) and spectroscopic data.

Summary prepared August 2008 by Andy Dicks at the University of Toronto and September 2008 by Douglas M. Young at the University of Oregon.

Source

Aktoudianakis, E.; Chan, E.; Edward, A. R.; Jarosz, I.; Lee, V.; Mui, L.; Thatipamala, S. S.; Dicks, A. P. J. Chem. Educ., Print 2008, 85, pp 555-557.

J. Chem. Educ. (Abstract only)

Category Descriptors

Chemistry Concepts
  • Aqueous Solution Chemistry
  • Aromatic Compounds
  • Catalysis
  • Organometallics
  • Phenols
  • Solid-Support Reagents
  • Water - Water Chemistry
Laboratory Techniques
  • Assembly of Reaction Apparatus
  • Heating and Cooling Methods
  • IR Spectroscopy
  • Melting Points and Melting Ranges
  • Microscale Lab
  • NMR Spectroscopy
  • pH
  • Recrystallization
  • Vacuum Filtration
Green Chemistry Principles
  • Design Safer Chemicals and Products
  • Increase Energy Efficiency
  • Maximize Atom Economy
  • Prevent Waste
  • Use Catalysts
  • Use Safer Solvents/Reaction Conditions
Chemistry Subdiscipline
  • Inorganic Chemistry
  • Organic Chemistry
Target Audience
  • Colleges/Universities
Source
  • Journal Articles