Synthesis 2014; 46(23): 3185-3190
DOI: 10.1055/s-0034-1379013
paper
© Georg Thieme Verlag Stuttgart · New York

Regioselective Monoarylation of 2-Phenylbenzimidazole via Ruthenium-Catalyzed­ C–H Bond Functionalization

Yasuyuki Kobayashi
Department of Bioscience and Informatics, Graduate School of Life and Environmental Sciences, Osaka Prefecture University, 1-1 Gakuencho, Nakaku, Sakai, Osaka 599-8531, Japan   Fax: +81(72)2549469   Email: tanimori@bioinfo.osakafu-u.ac.jp
,
Mitsuhiro Kashiwa
Department of Bioscience and Informatics, Graduate School of Life and Environmental Sciences, Osaka Prefecture University, 1-1 Gakuencho, Nakaku, Sakai, Osaka 599-8531, Japan   Fax: +81(72)2549469   Email: tanimori@bioinfo.osakafu-u.ac.jp
,
Motohiro Sonoda
Department of Bioscience and Informatics, Graduate School of Life and Environmental Sciences, Osaka Prefecture University, 1-1 Gakuencho, Nakaku, Sakai, Osaka 599-8531, Japan   Fax: +81(72)2549469   Email: tanimori@bioinfo.osakafu-u.ac.jp
,
Mitsunori Kirihata
Department of Bioscience and Informatics, Graduate School of Life and Environmental Sciences, Osaka Prefecture University, 1-1 Gakuencho, Nakaku, Sakai, Osaka 599-8531, Japan   Fax: +81(72)2549469   Email: tanimori@bioinfo.osakafu-u.ac.jp
,
Shinji Tanimori*
Department of Bioscience and Informatics, Graduate School of Life and Environmental Sciences, Osaka Prefecture University, 1-1 Gakuencho, Nakaku, Sakai, Osaka 599-8531, Japan   Fax: +81(72)2549469   Email: tanimori@bioinfo.osakafu-u.ac.jp
› Author Affiliations
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

 
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