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Synfacts 2007(8): 0806-0806
DOI: 10.1055/s-2007-968795
DOI: 10.1055/s-2007-968795
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Rh-Catalyzed C-H Activation Route to 2-Alkylpyridines and 2-Alkylquinolines
J. C. Lewis, R. G. Bergman*, J. A. Ellman*
University of California and Lawrence Berkeley National Laboratory, Berkeley, USA
Further Information
Publication History
Publication Date:
24 July 2007 (online)
Significance
A direct route to 2-alkylpyridines and quinolines from the respective heterocycles and olefins via Rh-catalyzed C-H activation has been developed. In this process, the substitution ortho to the heterocycle ring nitrogen, which presumably drives the equilibrium from an N-Rh to a C-Rh complex, is required to obtain alkylated products in high yields. In the pyridine series, the scope and limitations of the reaction were not well tested compared to the quinoline series. The TIPS-substituted alkylated product is readily desilylated or may be potentially used for fluoride-mediated carbodesilylation processes in reaction with aromatic aldehydes.