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By an efficient biomimetic synthetic method, several novel 2-substituted benzimidazoles, benzoxazoles, and benzothiadazole were readily prepared in good yields under mild conditions with 2-substituted imidazolinium iodides as the tetrahydrofolate model compounds at the oxidation level of formate. The reaction is probably involved in a nucleophilic addition to the C=N bond at the imidazolinium ring, followed a 1,3-H migration at an imidazolidine intermediate and a salt elimination.