Switchable, Reagent-Controlled C(sp³)-H Selective Iodination and Acetoxylation of 8-Methylquinolines

Abstract

An efficient Pd-catalyzed C­(sp3)-H selective iodination of 8-methylquinolines is reported herein for the first time. Because of the versatility of organic iodides, the method offers a facile access to various C8-substituted quinolines. By slightly switching the reaction conditions, an efficient C­(sp3)-H acetoxylation of 8-methylquinolines has also been enabled. Both approaches feature mild reaction conditions, good tolerance of functional groups, and a broad substrate scope.

Phenyliodine(III)diacetate (PIDA): Applications in Organic Synthesis

“…The more difficult site-selective C(sp 3 )-H activation/functionalization of 8-methylquinoline is particularly noteworthy in this domain. A report was developed by Jia et al on an effective Pd-catalyzed C(sp 3 )-H selective iodination of 8-methylquinolines ( 18) [17]. The method provided simple access to a variety of C8-substituted quinolines due to the adaptability of organic iodides (Scheme 3).…”