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. 2007 May 2;129(17):5332-3.
doi: 10.1021/ja070388z. Epub 2007 Apr 6.

Rh(I)-catalyzed alkylation of quinolines and pyridines via C-H bond activation

Jared C Lewis  1 , Robert G Bergman, Jonathan A Ellman
Affiliations

Rh(I)-catalyzed alkylation of quinolines and pyridines via C-H bond activation

Jared C Lewis et al. J Am Chem Soc. .

Abstract

The scope of heterocycle ortho-alkylation has been dramatically expanded to include pharmaceutically important pyridines and quinolines, which contain only a single nitrogen. The reactions, which are conducted at a high concentration (0.8 M), can be performed with catalyst loadings as low as 1% Rh. Substitution ortho to the heterocycle ring nitrogen is required for efficient alkylation and is consistent with the intermediacy of a Rh-carbene intermediate similar to those proposed in our earlier work.

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