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Synfacts 2009(10): 1076-1076
DOI: 10.1055/s-0029-1217902
DOI: 10.1055/s-0029-1217902
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Indolines by Pd(II)-Catalyzed Amination of C-H Bond
T.-S. Mei, X. Wang, J.-Q. Yu*
The Scripps Research Institute, La Jolla, USA
Further Information
Publication History
Publication Date:
22 September 2009 (online)
Significance
A palladium-catalyzed synthesis of indoline via intramolecular amination of a C-H bond is reported. Both single-electron [Ce(IV)] and two-electron (F+) oxidants are applicable to accomplish this reaction in comparable yields. The products can be readily converted into indoles by addition of other oxidants, e.g. Mn(OAc)3. Notably, for a highly electron-rich substrate (R¹ = 3,4-OCH2O) the indole was directly formed. Tetrahydroquinolines can be prepared by this procedure, but the yields are low.
Review: A. R. Dick, M. S. Sanford Tetrahedron 2006, 62, 2439.
Book: The Alkaloids: Chemistry and Biology, Vol. 50; G. A. Cordell, Ed.; Academic Press: San Diego, 1998.