Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 17, Pages 9243-9252Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b01723
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Funding
- NIH [R35GM122473]
- Pfizer
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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.
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