Rh(iii)-catalyzed regioselective C6-arylation of 2-pyridones with diazonaphthalen-2(1H)-ones along with directing group migration

Abstract

Herein, an unprecedented Rh(III)-catalyzed C6-arylation of N-pyridyl-2-pyridones with diazonaphthalen-2(1H)-ones along with directing group migration leading to the formation of 6-(2-(pyridin-2-yloxy)naphthalen-1-yl)pyridin-2(1H)-ones is reported. The reaction goes through a cascade process including C–H bond metalation, carbene formation, migratory insertion, and nucleophilic attack of the hydroxyl group of the in situ introduced naphthol moiety onto the pyridyl unit, followed by pyridyl migration. Importantly, this method has been effectively applied to the synthesis of several drug analogues, such as gemfibrozil, ibuprofen, and menthol. Moreover, it exhibits excellent atom- and step-economy, along with remarkable compatibility of functional groups, and high efficiency.