Iron(0)-Catalyzed Transfer Hydrogenative Condensation of Nitroarenes with Alcohols: A Straightforward Approach to Benzoxazoles, Benzothiazoles, and Benzimidazoles
Ramachandra Reddy Putta, Simin Chun, Seung Hyun Choi, Seok Beom Lee, Dong‐Chan Oh, Suckchang Hong
Abstract
The iron-catalyzed hydrogen transfer strategy has been applied to the redox condensation of o-hydroxynitrobenzene with alcohol, leading to the formation of benzoxazole derivatives. A wide range of 2-substituted benzoxazoles were synthesized in good to excellent yields without the addition of an external redox agent. A series of control experiments provided a plausible mechanism. Furthermore, the reaction system was successfully extended to the synthesis of benzothiazoles and benzimidazoles.
Topics & Concepts
BenzoxazoleChemistryCatalysisRedoxCondensationCombinatorial chemistryTransfer hydrogenationCondensation reactionAlcoholAlcohol oxidationOrganic chemistryRutheniumPhysicsThermodynamicsAsymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions