Regioselective arylation of 2 '-deoxyribonucleosides on amido or imino sites by copper(II)-mediated direct coupling with arylboronic acids

摘要

N-1-Aryl derivatives of 2'-deoxyguanosine (dG) were synthesized by copper(II)-mediated coupling of dG with arylboronic acids. Analogous aryl derivatives of 2'-deoxyinosine (dIn), 2'-deoxyuridine (dU), thymidine (T), 2'-deoxyadenosine (dA), and 2'-deoxycytidine (dC) were also conveniently synthesized by this method. Arylation took place preferentially on the amido functions in dG and dIn and the imino functions in dU or T. Remarkably, the nucleosides themselves served as internal ligands as well as reactants. (c) 2005 Elsevier Ltd. All rights reserved.