Transition‐Metal‐Free Regioselective Alkylation of Quinoline N‐Oxides via Oxidative Alkyl Migration and C−C Bond Cleavage of tert‐/sec‐Alcohols

Abstract

Abstract An unprecedented C2‐alkylation of quinoline N‐oxide derivatives via C−C bond activation of tert‐ and sec ‐alkyl alcohol is described using hypervalent iodine (III) reagent PhI(OAc) 2 (PIDA). This regioselective alkylation using mild hypervalent iodine reagents is more practical, operationally simple and transition metal free. The reaction proceeds efficiently with a broad range of substrates including quinoline, isoquinoline, and pyridine N‐oxides using a variety of tert ‐/ sec ‐ alcohols. From experimental outcome, we also propose a rationalized mechanism, mediated by PIDA. magnified image