4 years ago

C2-Selective Branched Alkylation of Benzimidazoles by Rhodium(I)-Catalyzed C–H Activation

C2-Selective Branched Alkylation of Benzimidazoles by Rhodium(I)-Catalyzed C–H Activation
Jonathan A. Ellman, Kevin D. Hesp, Danielle Confair, Vincent Mascitti, Gaël Tran
Herein, we report a Rh(I)/bisphosphine/K3PO4 catalytic system allowing for the first time the selective branched C–H alkylation of benzimidazoles with Michael acceptors. Branched alkylation with N,N-dimethyl acrylamide was successfully applied to the alkylation of a broad range of benzimidazoles incorporating a variety of N-substituents and with both electron-rich and -poor functionality displayed at different sites of the arene. Moreover, the introduction of a quaternary carbon was achieved by alkylation with ethyl methacrylate. The method was also shown to be applicable to the C2-selective branched alkylation of azabenzimidazoles.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01723

DOI: 10.1021/acs.joc.7b01723

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