1. Cross Coupling Reaction
1) Stille Reaction
2) Suzuki Reaction
3) Sonogashira Reaction

3. Carbonylative Cross Coupling Reaction

4. 1) Stille coupling 반응

6. Intramolecular Stille Reaction

8. Recycle of Sn

10. 2) Suzuki coupling Reaction

12. Intramolecular Suzuki Reaction

13. Synthesis of Bombyokol
Aromatic boronic acid

14. Unreactive Compounds Reactivity of Halide:
vinyl iodide, vinyl bromide》aryl iodide > vinylchloride 》aryl bromide,
Reactivity of Catalysts:
PdCl2(PPh3)2, Pd(PPh3)4, Pd(OAc)2, PdCl2

15. 3) Sonogashira coupling

18. Anticancer nucloside
Metal acetylide: Sn, Zn, Mg

19. Wacker Process

20. Historically, in 1894 Phillips reported that acetaldehyde
and Pd(0) was isolated from ethylene gas and
aqueous PdCl2.
This was further developed by using CuCl2 and O2.