1. Reporter: Yu Ting Huang Advising Prof: Ru Jong Jeng 1

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 2

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-ichi Negishi for their effort for discovery and development of palladium-catalyzed cross couplings in organic synthesis. 3 Richard F. Heck Akira SuzukiEi-ichi Negishi

4. Suzuki Reaction and Stille Reaction 4 Ar: the relative reactivity appears to be PhI >p-ClC,H,Br > PhBr > o-MeC,H,Br > o-MeOC,H,Br. A. Suzuki, Chem. Commun. 1979, 866. 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 5

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

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

8. 8

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 9

10. Conjugated microporous polymers 10 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 11 T. Yokozawa, et al, J. AM. CHEM. SOC. 2007, 129, 7236 Polyfluorene Polyfluorenes are an important class of polymers which have the potential to act as both electroactive and photoactive materials.

12. Hyperbranched polyfluorenes 12 W. Huang, et al, Macromolecules, 2005, 38, 6755

13. Organic Solar cell 13 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 14

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

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

17. 17 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 Gao, Y. J. Org. Chem.2006, 71, 537.

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 18

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. 19