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Synfacts 2013; 9(1): 0029
DOI: 10.1055/s-0032-1317862
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Phenyliodine(III) Diacetate-Promoted Synthesis of Benzimidazoles

Contributor(s):
Victor Snieckus
,
Ashish Maheta
Huang J, He Y, Wang Y, Zhu Q * Guangzhou Institutes of Biomedicine and Health, P. R. of China
Synthesis of Benzimidazoles by PIDA-Promoted Direct C(sp2)–H Imidation of N-Arylamidines.

Chem. Eur. J. 2012;
18: 13964-13967
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Further Information

Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

arylbenzamidines - phenyliodine(III) diacetate - benzimidazoles - C–H imidation

Significance

Reported is the synthesis of 2-substituted benzimidazoles by the reaction of N-arylamidines with phenyliodine(III) diacetate under mild conditions via an intramolecular oxidative imidation process. The C–H activation reaction is proposed to proceed by the formation of free radical intermediates which was partially supported by a free radical inhibition experiment.


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Comment

Compounds containing the benzimidazole moiety are reported to possess a number of interesting biological activities (K. Vijaykumar, A. J. Ahemed J. Chem. Pharm. Res. 2010, 2, 215). Several syntheses of similar 2-substituted benzimidazoles have been reported involving an intramolecular Cu-catalyzed N-arylation (C. Chen et al. J. Org. Chem. 2011, 76, 716). In comparison, the present synthesis occurs under metal-free, mild conditions. However, the reaction suffers from poor regioselectivity for meta-substituted substrates, leading to mixture of isomers.


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