1. 1 C) Internship in Research Arylation of trimethylvinylsilane. Synthesis of (E)-1-iodo-2-arylethylenes and of (E,E)-1,4-diarylbuta-1,3-dienes by Heck reaction Supervisor : Dr Jeffery Laboratoire de Synthèse Organique Sélective et Chimie Organométallique February to July 2004

2. 2 Objectives : syntheses of diarylbutadienes Heck reaction

3. 3 Heck, R. F. Org. React. 1982, 27, 345-390

4. 4 Arylation of trimethylvinylsilane Jeffery, T. Tetrahedron Lett. 2000, 41, 8445-8449 Addition of R 4 N + X - :  reaction are faster and more selective  Choice of catalytic system [Pd/Base/QX] can change the selectivity

5. 5 Arylation of trimethylvinylsilane Jeffery, T. Tetrahedron Lett. 1999, 40, 1673-1676 Toluene, 20°C

6. 6 Iodation

7. 7 Results

8. 8 One pot synthesis T. Jeffery, T.; Ferber, B. Tetrahedron Lett. 2003, 44, 193-197 Heck reaction

9. 9 One pot synthesis

10. 10 Results

11. 11 Conclusion