Indium in Organic Synthesis

1. Indium in Organic Synthesis Huang-Jianzhou 2012-04-14

2. Content 1、Introduction 2、 Preparation of Allylindium 3、As Lewis Acid 4、Cross coupling 5、Reduction 6、Conclusion

3. 1、Introduction 5s2 5p1 1863 J. Uziel, Synthesis, 2007, 1739. Scott E. Denmark, Chem. Rev. 2003, 103, 2763 Basi V. Subba Reddy, Eur. J. Org. Chem. 2010, 591 Sujit Roy, Chem. Rev. 2010, 110, 2472 Anthony J. Downs, Chem. Rev. 2007, 107, 2 化合价：0, +1,+2,+3 Advantagesindium in organic synthsis: • stable in air and water • Notoxicity for man • Low first ionization potential, can be an effective single electron transfer agent • organoindium reagents are easy prepared

5. Regioselectivity

7. Diastereoselectivity

9. 2、Preparation of Allylindium

13. allenes

15. allylindium intermediate The reactivity of the allyl halide ：I≈ Br >> Cl, F inactive

16. Addition to C=O Bonds 16

18. Asymmetry

19. Addition to C=N Bonds

20. Asymmetry

23. Addition to C-C Multiple Bonds

24. Other ways 24

25. 3、As Lewis Acid

27. Coniaene reaction

30. Aldol, Minnich, D-A Reaction

31. Carbonyl-ene Reactions

32. 5、Cross-Coupling

34. 4、Reduction

35. Reductive Aldol Reaction

37. 6、Conclusion • Indium and its salts provide various methodologies for formation C-C bond, with high reactivity and the unique selectivity; • Work is still ongoing, especially in enantioselective reactions.

38. Thank You !