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J Org Chem. 2017 Sep 1;82(17):9243-9252. doi: 10.1021/acs.joc.7b01723. Epub 2017 Aug 22.

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

Author information

1
Department of Chemistry, Yale University , 225 Prospect Street, New Haven, Connecticut 06520, United States.
2
Medicinal Sciences, Pfizer, Inc. , Groton, Connecticut 06340, United States.

Abstract

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.

PMID:
28828857
PMCID:
PMC5585739
DOI:
10.1021/acs.joc.7b01723
[Indexed for MEDLINE]
Free PMC Article

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