Indium in Organic Synthesis Huang-Jianzhou

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

化合价： 0, +1,+2, s2 5p1 J. Uziel, Synthesis, 2007, 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 Advantages indium 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 1 、 Introduction

4

Regioselectivity 5

6

Diastereoselectivity

8

9 2 、 Preparation of Allylindium

11

13 allenes

14

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

16 Addition to C=O Bonds

Asymmetry

Addition to C=N Bonds

Asymmetry

Addition to C-C Multiple Bonds

24 Other ways

3 、 As Lewis Acid

Coniaene reaction

Aldol, Minnich, D-A Reaction

Carbonyl-ene Reactions

5 、 Cross-Coupling

4 、 Reduction

Reductive Aldol Reaction

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.