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Indium in Organic Synthesis

Indium in Organic Synthesis. Huang-Jianzhou 2012-04-14. Content. 1 、 Introduction. 2 、 Preparation of Allylindium. 3 、 As Lewis Acid. 4 、 Cross coupling. 5 、 Reduction. 6 、 Conclusion. 1 、 Introduction. 5s2 5p1. 1863. J. Uziel, Synthesis, 2007 , 1739.

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Indium in Organic Synthesis

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  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

  4. Regioselectivity

  5. Diastereoselectivity

  6. 2、Preparation of Allylindium

  7. allenes

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

  9. Addition to C=O Bonds 16

  10. Asymmetry

  11. Addition to C=N Bonds

  12. Asymmetry

  13. Addition to C-C Multiple Bonds

  14. Other ways 24

  15. 3、As Lewis Acid

  16. Coniaene reaction

  17. Aldol, Minnich, D-A Reaction

  18. Carbonyl-ene Reactions

  19. 5、Cross-Coupling

  20. 4、Reduction

  21. Reductive Aldol Reaction

  22. 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.

  23. Thank You !

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