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Synthesis 2014; 46(23): 3185-3190
DOI: 10.1055/s-0034-1379013
DOI: 10.1055/s-0034-1379013
paper
Regioselective Monoarylation of 2-Phenylbenzimidazole via Ruthenium-Catalyzed C–H Bond Functionalization
Further Information
Publication History
Received: 04 June 2014
Accepted after revision: 01 August 2014
Publication Date:
28 August 2014 (online)
Abstract
The highly regioselective monoarylation of 1-methyl-2-phenyl-1H-benzimidazole has been demonstrated. The reaction of 1-methyl-2-phenyl-1H-benzimidazole with 4-iodoanisole provided 2-(4′-methoxybiphenyl-2-yl)-1-methyl-1H-benzimidazole as the sole product in 96% isolated yield in the presence of [RuCl2(p-cymene)]2 and triphenylphosphine as precatalysts. A series of novel 2-(biphenyl-2-yl)benzimidazoles have been synthesized in good to excellent yields.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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Recent reviews on C–H functionalization using transition metals:
For a recent review of approaches to 2-arylbenzimidazoles, see
Although the efficient and highly regioselective introductions of an aryl group into related arylazoles, particularly 1-methyl-2-phenylimidazole, under ruthenium-catalyzed conditions have been reported, the application using benzimidazole has not yet been documented, see:
Palladium-catalyzed arylations have also been reported, see: