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CDC Reaction Involving α - C-H Bonds of Nitrogen in Amines

CDC Reaction Involving α - C-H Bonds of Nitrogen in Amines. 李 南 2012.6.16. 一般形式. Yoshida, J. Am. Chem. Soc. 1999 , 121 , 9546. Conditions A: 2.5 equivH 2 O 2 ; Conditions B: 60 o C , 1 atmO 2 . Murahashi , S.- I. J. Am. Chem. Soc . 2003 , 125 , 15312.

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CDC Reaction Involving α - C-H Bonds of Nitrogen in Amines

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  1. CDC Reaction Involving α -C-H Bonds ofNitrogen in Amines 李南 2012.6.16

  2. 一般形式 Yoshida, J. Am. Chem. Soc. 1999, 121, 9546.

  3. Conditions A: 2.5 equivH2O2; Conditions B: 60 oC, 1 atmO2. Murahashi, S.-I. J. Am. Chem. Soc. 2003, 125, 15312. Murahashi, S.-I., Angew. Chem., Int. Ed. 2005, 44, 6931. Murahashi, S.-I., J. Am.Chem. Soc. 2008, 130, 11005.

  4. Ofial, Chem. Commun., 2009, 45, 5024. BirSain, Chem. Commun., 2009, 45, 2371. Zhu, C.-J., Chem. Commun., 2011, 47, 2354.

  5. Li, C.-J. J. Am. Chem. Soc.,2004, 126, 11810.

  6. Fu Hua, J. Org. Chem., 2008, 73, 3961. Li, C.-J.,Org. Lett.,2004, 6, 4997. Li, C.-J., Tetrahedron: Asymmetry, 2006, 17, 590.

  7. Pierre Vogel,Org. Lett.,2009, 11, 1701.

  8. Li, C.-J.,J. Am. Chem. Soc. 2005, 127, 6968.

  9. Huang, Z.-Z. Org. Lett. 2010, 12, 5214. Che, C-M., Chem. Commun. 2010, 46, 2739.

  10. RamaiahPrabhu, Chem. Commun., 2011, 47,11787.

  11. Kawakami, Y., Angew. Chem., Int. Ed. 2004, 43, 4231.

  12. Itami, K., Chem. Asian J., 2009, 4, 1416.

  13. Conditions A: ∼80 equivnitroalkane, 1.0-1.2 equivtBuOOH; Conditions B: 5 equivnitroalkane, 1 atm O2, H2O, 40-60 oC. Li, C.-J. J. Am. Chem. Soc.,2005, 127, 3672. Li, C.-J. Green Chem.,2007, 9, 1047.

  14. Stephenson, C. R. J., J. Am. Chem. Soc. 2010,132, 1464.

  15. Zhu, C.-J., Angew. Chem., Int. Ed. 2012, 51, 1252.

  16. Conditions A: 2.5 equivH2O2; Conditions B: 60 oC, 1 atmO2, H2O. Li, C.-J. Green Chem. 2007, 9, 1047. Li, C.-J. Eur. J. Org. Chem. 2005, 3173.

  17. Mikiko Sodeoka. J. Am. Chem. Soc. 2006, 128, 14010.

  18. Li, C.-J. Angew. Chem., Int. Ed. 2008, 47, 7075.

  19. Wang, Rui,Angew. Chem., Int. Ed.2011, 123, 10613.

  20. Klussmann, M. Chem. Commun.2009, 45, 3169. Guo, C-C., Chem. Commun. 2009, 45, 953.

  21. Magnus Rueping, Chem. Commun., 2011, 47, 2360.

  22. Chi, R. Y. Angew. Chem. Int. Ed. 2012,51, 3649. Klussmann, M. Synlett2009, 10, 1558.

  23. X= O, S, CH2, (CH2)2 Huang, Z.-Z. Angew. Chem., Int. Ed. 2010,49, 10181.

  24. Conclusion 1. Although using simple and inexpensive building blocks is an attractive alternative to consuming more functionalized and costly reagents, chemo- and regioselectivity remain issues that limit the broad usage of these methods. 2. Practical approaches to C-H bond oxidation using reagents that are more environmentally friendly, such as oxygen, electricity, and visible light, are desirable and are being developed. 3. In terms of asymmetric catalysis, enantioselective C-C bond formation by C-H bond oxidation is still in its infancy, although ligand-accelerated transition metal catalysis and organocatalysis has enabled some growth.

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