Suzuki Reaction

1. Suzuki Reaction Reporter: Yu Ting Huang Advising Prof:RuJongJeng

2. Outline • Introduction • Chemistry of Suzuki Reaction • Reaction mechanism • Boron reagents • Recent development of Suzuki Reaction • Conjugated microporous polymers • Light-emitting diodes • Organic Solar cell • Polymer-bound palladium catalyst in Suzuki Reaction • Conclusions

3. Introduction • The Suzuki reaction is the organic reaction that is classified as a coupling reaction where the coupling partners are a boronic acid with a halide catalyzed by a palladium(0) complex • It was first published in 1979 by Akira Suzuki and he shared the 2010 Nobel Prize in Chemistry with Richard F. Heck and Ei-ichiNegishi for their effort for discovery and development of palladium-catalyzed cross couplings in organic synthesis. Ei-ichiNegishi  Akira Suzuki Richard F. Heck

4. Suzuki Reaction and Stille Reaction  A.Suzuki,  Chem. Commun.1979, 866. Ar: the relative reactivity appears to be PhI >p-ClC,H,Br > PhBr > o-MeC,H,Br > o-MeOC,H,Br. Stille Reaction   J. K. Stille,  Angew. Chem. Int. Ed. Engl.1986, 25, 508

5. Outline • Introduction • Chemistry of Suzuki Reaction • Reaction mechanism • Boron reagents • Recent development of Suzuki Reaction • Conjugated microporous polymers • Light-emitting diodes • Organic Solar cell • Polymer-bound palladium catalyst in Suzuki Reaction • Conclusions

6. Reaction mechanism Guy C. Lloyd-Jones., et al, Chem. Soc. Rev., 2014, 43, 412

7. Boron reagents Guy C. Lloyd-Jones., et al, Chem. Soc. Rev., 2014, 43, 412

8. Guy C. Lloyd-Jones., et al, Chem. Soc. Rev., 2014, 43, 412

9. Outline • Introduction • Chemistry of Suzuki Reaction • Reaction mechanism • Boron reagents • Recent development of Suzuki Reaction • Conjugated microporous polymers • Organic light-emitting diodes • Organic Solar cell • Polymer-bound palladium catalyst in Suzuki Reaction • Conclusions

10. Conjugated microporous polymers A. I. Cooper, et al, Angew. Chem., Int. Ed., 2012, 51, 12727–12731. Subi J. George, et al, J. Mater. Chem., 2011, 21, 12958 Han, B.-H.,et al, Macromolecules, 2011, 44, 5573.

11. Organic light-emitting diodes Polyfluorene T. Yokozawa, et al, J. AM. CHEM. SOC. 2007, 129, 7236 Polyfluorenes are an important class of polymers which have the potential to act as both electroactive and photoactive materials.

12. Hyperbranchedpolyfluorenes W. Huang, et al, Macromolecules, 2005, 38, 6755

13. Organic Solar cell Z. K. Chen, et al, J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 5266.

14. Outline • Introduction • Chemistry of Suzuki Reaction • Reaction mechanism • Boron reagents • Recent development of Suzuki Reaction • Conjugated microporous polymers • Light-emitting diodes • Organic Solar cell • Polymer-bound palladium catalyst in Suzuki Reaction • Conclusions

15. Polymer-bound palladium catalyst C. Le Drian, et al, Tetrahedron Lett. 1998, 39, 4287 W.-C. Shieh, et al, Synth. Commun. 2002, 32, 1059.

16. S. Ikegami, et al, Org. Lett. 2002, 4, 3371.

17. Gao, Y. J. Org. Chem.2006, 71, 537. SCHEME 1. Schematic Representation of Magnetic Nanoparticle Facilitated Solid-Phase Suzuki Cross Coupling Reactions SCHEME 2. Immobilization of Pd-NHC Complexes onto the Surface of Iron Oxide Nanoparticles

18. Outline • Introduction • Chemistry of Suzuki Reaction • Reaction mechanism • Boron reagents • Recent development of Suzuki Reaction • Conjugated microporous polymers • Light-emitting diodes • Organic Solar cell • Polymer-bound palladium catalyst in Suzuki Reaction • Conclusions

19. Conclusions • We can use different boron reagent for different kinds of suzuki reaction. • Suzuki reaction is a good way to prepare conjugated polymer. • In green chemistry, the catalyst can be recycled is a better choice.