Metal-Free Synthesis of Benzimidazoles via Oxidative Cyclization of <scp>d</scp>-Glucose with <i>o</i>-Phenylenediamines in Water
Dineshkumar Raja, Abigail Philips, Pushbaraj Palani, Wei‐Yu Lin, S. Devikala, Gopal Chandru Senadi
Abstract
d-Glucose has been identified as an efficient C1 synthon in the synthesis of benzimidazoles from o-phenylenediamines via an oxidative cyclization strategy. Isotopic studies with 13C6-d-glucose and D2O unambiguously confirmed the source of methine. The notable features of this method include the following: broad functional group tolerance, a biorenewable methine source, excellent reaction yields, a short reaction time, water as an environmentally benign solvent, and the synthesis of vitamin B12 component on the gram scale.
Topics & Concepts
ChemistrySynthonOxidative phosphorylationSolventChemical synthesisCombinatorial chemistryOrganic chemistryBiochemistryIn vitroCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisCatalytic Cross-Coupling Reactions