Cobalt-catalyzed peri-selective alkoxylation of 1-naphthylamine derivatives

Beilstein J Org Chem. 2018 Aug 9:14:2090-2097. doi: 10.3762/bjoc.14.183. eCollection 2018.

Abstract

A cobalt-catalyzed C(sp2)-H alkoxylation of 1-naphthylamine derivatives has been disclosed, which represents an efficient approach to synthesize aryl ethers with broad functional group tolerance. It is noteworthy that secondary alcohols, such as hexafluoroisopropanol, isopropanol, isobutanol, and isopentanol, were well tolerated under the current catalytic system. Moreover, a series of biologically relevant fluorine-aryl ethers were easily obtained under mild reaction conditions after the removal of the directing group.

Keywords: 1-naphthylamines; C–H activation; alkoxylation; cobalt catalysis; secondary alcohols.