CENTENNIAL HONORS COLLEGE
Western Illinois University
Undergraduate Research Day 2015
Poster Presentation
Palladium Catalyzed Sonogashira Coupling with Diaryl Tellurides
Victoria Valde
Faculty Mentor: Shaozhong Zhang
Chemistry
Carbon-carbon bond forming reactions are important in the production of many man-made chemicals
such as pharmaceuticals and plastics. Palladium catalyzed cross-coupling reactions are the most important
methods used for the formation of carbon-carbon bonds in organic chemistry. Sonogashira coupling
reaction is a palladium-catalyzed cross-coupling reaction of terminal alkynes with aryl or alkenyl halides
in the presence of a co-catalyst cuprous iodide. It is the main pathway for the synthesis of aryl alkynes
and conjugated enynes. The reaction has become an essential tool in the synthesis of these compounds,
which have applications in natural products chemistry, pharmaceuticals, and material science. The
objective of our research is to study Sonogashira coupling reaction of diaryl tellurides with terminal
alkynes.
We found that the reaction was well done when Pd(dppf)Cl2 was used as the catalyst. Then the best
reaction condition was applied to synthesize various Sonogashira coupling products. For example, a
diaryl telluride was reacted with various terminal alkynes such as phenylacetylene, 1-hexyne, 1-octyne
and 1-heptyne under the optimized condition to yield different coupling products. This process resulted in
good yield of coupling products at very mild reaction conditions. The synthesized coupling products were
characterized by proton nuclear magnetic resonance spectroscopy.