The successful realization of direct palladium-catalyzed C8-fluoroalkylation and C8-fluoroalkenylation of naphthalene derivatives has been accomplished, employing iodonium salts as coupling partners. The reactions exhibited complete C8-regioselectivity, and diverse carbonyl groups were identified as effective directing groups.

Abstract

In this study, two novel C8-functionalization methods of 1-carbonylnaphthalenes were developed. Leveraging iodonium triflates as coupling partners, we disclose palladium-catalyzed C8-fluoroalkylation and C8-fluoroalkenylation processes. These protocols exhibit broad applicability across diverse naphthalene derivatives, owing to carbonyl directing groups at the C1 position which can be retained for subsequent applications or selectively removed, enhancing the versatility of the developed methodologies.