Synthesis of Benzofuran Derivatives through Cascade Radical Cyclization/Intermolecular Coupling of 2-Azaallyls

Abstract

Benzofurans are among the most popular structural units in bioactive natural products, however, the synthesis of such structures by radical cyclization cascade reactions is rare. Herein, we report a mild and broadly applicable method for the construction of complex benzofurylethylamine derivatives through a unique radical cyclization cascade mechanism. Single-electron transfer (SET) from 2-azaallyl anions to 2-iodo aryl allenyl ethers initiates a radical cyclization that is followed by intermolecular radical-radical coupling. This expedient approach enables the synthesis of a range of polycyclic benzofurans that would otherwise be difficult to prepare.

Keywords: azaallyl anions; benzofurylethylamine; cascade reactions; radical coupling; radical cyclization.