Oxidation of substituted pyridines PyrCHRSiMe3 (R=H, Me, Ph) and substituted quinolines QnCH2SiMe3 with hypervalent iodine reagents

Article abstract of DOI:10.3987/com-96-7397

Oxidation of a variety of substituted pyridines, PyrCHRSiMe₃ (R = H, Me, Ph) and quinolines, QnCH₂SiMe₃ with hypervalent iodine reagents PIDA, (PhI(OCOCH₃)₂) and PIFA, (PhI(OCOCF₃)₂) has been studied. Oxy-desilylation with PIDA/TBAF gives low to moderate yields of PyrCHROR¹ and QnCH₂OR¹ (R¹ = H, Ac), while good yields of PyrCHROH and QnCH₂OH are obtained when PIFA is used.