Super-Electron-Donor 2-Azaallyl Anions Enable Construction of Isoquinolines

Org Lett. 2022 Mar 11;24(9):1786-1790. doi: 10.1021/acs.orglett.2c00140. Epub 2022 Feb 25.

Abstract

Herein is introduced the application of "super-electron-donor"(SED) 2-azaallyl anions in a tandem reduction/radical cyclization/radical coupling/aromatization protocol that enables the rapid construction of isoquinolines. The value of this transition-metal-free method is highlighted by the wide range of isoquinoline ethyl amines prepared with good functional group tolerance and yields. An operationally simple gram scale synthesis is also conducted, confirming the scalability.