Hydrogen-bond-driven electrophilic activation for selectivity control: scope and limitations of fluorous alcohol-promoted selective formation of 1, 2-disubstituted …

…, D Kumar, N Bollineni, AK Chakraborti

Index: Chebolu, Rajesh; Kommi, Damodara N.; Kumar, Dinesh; Bollineni, Narendra; Chakraborti, Asit K. Journal of Organic Chemistry, 2012 , vol. 77, # 22 p. 10158 - 10167

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Citation Number: 41

Abstract

Hydrogen-bond-driven electrophilic activation for selectivity control during competitive formation of 1, 2-disubstituted and 2-substituted benzimidazoles from o-phenylenediamine and aldehydes is reported. The fluorous alcohols trifluoroethanol and hexafluoro-2-propanol efficiently promote the cyclocondensation of o-phenylenediamine with aldehydes to afford selectively the 1, 2-disubstituted benzimidazoles at rt in short times. A mechanistic insight ...