Palladium-Catalyzed Coordination-Induced Remote C-H Aryl Etherification/Amination of 8-Amidoquinolines

Org Lett. 2024 Aug 9;26(31):6562-6567. doi: 10.1021/acs.orglett.4c02061. Epub 2024 Jul 30.

Abstract

Herein, we report a direct method for palladium-catalyzed coordination-induced oxidative remote C-H aryl etherification of 8-amidoquinolines with p-benzoquinone monoacetal. The method provides access to C5-aryl etherified quinolines and shows site-selectivity different from that of typical palladium-catalyzed C(sp2)-H activation reactions. The p-benzoquinone monoacetals act both as oxidants and as aryl etherification reagents. By using proper substrates, C5-aminated quinolines and C4-etherifed 1-naphthylamine could also be formed.