“All-Aqueous” Tandem Boc-Deprotection and Alkylation of N-Bocbenzimidazole Derivatives under Visible Light with Alkyl Aryl Diazoacetates: Application to Site-Selective Insertion of Carbenes into the N–H Bond of Purines

Abstract

Herein, we have reported a blue LED-induced tandem Boc-deprotection and NH-alkylation of benzimidazole derivatives with methyl aryl diazoacetates. The reactions occur in water at room temperature. The desired products are obtained in good to excellent yields. The putative mechanism of this reaction is discussed based on control experiments and supported by DFT studies. Additionally, the strategy is used to alkylate various purine derivatives via site-selective N1-alkylation to generate acyclic nucleoside analogues.