Synthesis of fluorine-containing 6-arylpurine derivatives via Cp∗Co(III)-catalyzed C-H bond activation

Abstract

Cp∗Co(III)-catalyzed (Cp∗=pentamethylcyclopentadienyl) C-H bond functionalization of 6-arylpurines using gemdifluoroalkenes and allyl fluorides is described. The reaction with gem-difluoroalkenes afforded monofluoroalkenes with high (Z)-selectivity, while the reaction with allyl fluorides led to C-H allylation in moderate (Z)-selectivity. Both reactions proceeded using a user-friendly single-component catalyst [Cp∗Co(CH3CN)3](SbF6)2 in fluorinated alcohol solvents without any additives. Robustness was also demonstrated by a preparative-scale reaction under air.