Rhodium-Catalyzed Isoquinoline Synthesis Using Vinyl Selenone as Oxidizing Acetylene Surrogate

Org Lett. 2023 May 12;25(18):3206-3209. doi: 10.1021/acs.orglett.3c00826. Epub 2023 May 4.

Abstract

Isoquinoline is a privileged structure in many bioactive compounds and valuable ligands. Transition-metal-catalyzed oxidative annulation of imine derivatives has become a promising synthetic method; however, catalytic synthesis of 3,4-nonsubstituted isoquinolines by formal acetylene annulation has been scarce to date. Herein, we introduce vinyl selenone as an effective acetylene surrogate for the Rh-catalyzed annulative coupling under mild conditions. The Se fragment can be recovered as diselenide and recycled. The product can readily be converted to 1-aminoisoquinolines.