This document summarizes the development of a new methodology for synthesizing symmetrical biaryls using palladium-catalyzed detelluration of symmetrical diaryl tellurides. Key points discussed include: 1) Biaryls have applications in pharmaceuticals, agrochemicals, and polymers. 2) A new method is developed using palladium-catalyzed detelluration of symmetrical diaryl tellurides to synthesize various symmetrical biaryls. 3) This new method provides more benign alternatives for synthesizing biaryl-containing pharmaceutical drugs.

1. Development of new methodology to the
synthesis of symmetrical Biaryls
By
Souseelya K Vedula
Faculty Mentor: Dr. Jin Jin

2. • Introduction
• Applications of Biaryls
• Results and Discussion
• Experimental procedure
• Reaction Mechanism
• Conclusion
• Future work
• References

3. Introduction
• Biaryl compounds
• Coupling mechanisms
• Palladium catalyst : Widely used due to its stability to reaction
conditions and inertness.

4. Types of Palladium Catalysts
Homogenous Palladium Catalyst : Palladium is directly added to the
reaction mixture which makes the
recovery of the catalyst difficult.
Heterogeneous Palladium Catalyst: Palladium catalyst is attached to
a solid support which can be
removed after reaction and can
be reused.

5. Types of Coupling Reactions

6. Kumada coupling
Buchwald- Hartwig
Hiyama coupling

7. Applications
• Pharmaceutical Industry- Bi aryl scaffold forms the core of many
therapeutic classes such as antifungal,
anti-inflammatory, anti rheumatic and
anticancer drugs.
Allocolchicin – tubulin polymerization inhibitor Rhazinilam – tubulin polymerization / depolymerization
inhibitor
Baudoin, O., Cesario, M., Guenard, D. J.Org. Chem., 2002, 67, 1199-1207.

8. Applications
Biphenomycin- A novel peptide
• Agrochemicals
• Polymers
• Light emitting diodes
Carbonelle, A., Zhu, J. Org. Let., 2000, 2, 3477-3480

9. Results and Discussion

27. Results and Discussion

38. Experimental procedure
ArI ArTeAr
Te0
KOH, DMSO
110
o
C, 10 h
Scheme 1: Synthesis of symmetrial diaryl telluride ArTeAr

39. Experimental procedure
ArTeAr
PdCl2, Na2CO3
Ar-Ar
AgOAc, MeOH, rt 2h
Scheme 2: Synthesis of symmetrical biaryls by detelluration

40. Reaction Mechanism

41. Conclusion
• In our research , a new method to synthesize symmetrical bi aryls has
been developed by detelluration reaction of symmetrical diaryl
tellurides.
• Many biaryls with different functional groups have been synthesized
using this new technique.
• The new method to generate the biaryls will lead to more benign
alternatives in the field of pharmaceuticals in the synthesis of bi aryl
containing drugs.

42. Future work
• To synthesize more biaryl compounds of different substituents.
• To explore more aspects of organotellurium chemistry.

43. References
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• Baudoin, O., Cesario, M., Guenard, D. J.Org. Chem., 2002, 67, 1199-1207.
• Carbonelle, A., Zhu, J. Org. Let., 2000, 2, 3477-3480.
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45. Acknowledgement
• Dr. Jin Jin and Dr. Shaozhang Zang
• Department of Chemistry
• Western Illinois University
• Family and Friends