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.