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Sequential Ruthenium(II)-Acetate Catalyzed C–H Bond Diarylation in NMP or Water and Hydrosilylation of Imines

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Abstract

Ruthenium(II)-acetate catalysts are shown to promote sp2 C–H bond activation/diarylation of arylimines with aryl bromides selectively at ortho positions in both organic solvent (N-methylpyrrolidone, NMP) and in water. Water allows to produce a more active ruthenium catalyst for diarylation of ketimines. Furthermore, the diarylation of imines in water in basic media allows the access to diarylated aldehyde. Sequential catalytic C–H arylation/reduction using either a stoichiometric amount of NaBH3CN or via a ruthenium(II) catalytic hydrosilylation of the resulting imines offers a direct route to bulky secondary amines.

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Acknowledgments

The authors are grateful to CNRS, the French Ministry for Research, the Institut Universitaire de France (P. H. D.), the ANR program 09-Blanc-0101-01, and the Chinese Scholarship Council for a Ph.D. Grant to B. L.

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Authors and Affiliations

  1. UMR 6226 CNRS-Université de Rennes 1 Institut des Sciences Chimiques de Rennes - Team, Organometallics: Materials and Catalysis, Centre for Catalysis and Green Chemistry, Campus de Beaulieu, 35042, Rennes, France

    Bin Li, Charles B. Bheeter, Christophe Darcel & Pierre H. Dixneuf

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  1. Bin Li
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  2. Charles B. Bheeter
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  3. Christophe Darcel
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  4. Pierre H. Dixneuf
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Correspondence to Christophe Darcel or Pierre H. Dixneuf.

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Li, B., Bheeter, C.B., Darcel, C. et al. Sequential Ruthenium(II)-Acetate Catalyzed C–H Bond Diarylation in NMP or Water and Hydrosilylation of Imines. Top Catal 57, 833–842 (2014). https://doi.org/10.1007/s11244-014-0244-1

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