Updated
Feb 01, 2010

Rh(I)-catalyzed synthesis of indoles through the amino-Claisen rearrangement of N-propargylanilines
Saito et al. have reported a RhH(CO)(Ph₃P)₃ catalyzed synthesis of 2-substituted or 2,3-disubstituted indoles. They conclude from the NMR studies that the formation of indoles is derived from an o-allenylaniline intermediate, which is generated by the Rh(I)-catalyzed aromatic amino-Claisen rearrangement of N-propargylanilines. Moreover, they elucidate that the active catalyst is [Rh(CO)(Ph₃P)₂]OCH(CF₃)₂ generated in situ from RhH(CO)(Ph₃P)₃ and 1,1,1,3,3,3-hexafluoro-2-propanol. The catalyst structure is confirmed by single-crystal X-ray crystallographic analysis.
A. Saito, S. Oda, H. Fukaya, Y. Hanzawa, J. Org. Chem. 2009, 74, 1517.
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