Guilherme M. Martins

A solvent- and metal-free synthesis of 3-chacogenyl-indoles employing DMSO/I2 as an eco-friendly catalytic oxidation system.

Herein, we describe a solvent- and metal-free method for the synthesis of 3-chalcogenyl-indoles from indoles and diorganyl dichalcogenides using an equivalent amount of DMSO as an oxidant, under catalysis by molecular iodine. This mild and eco-friendly approach allowed the preparation of a wide range of 3-selenyl- and 3-sulfenyl-indoles in good to excellent yields.

SeCl2-Mediated Approach Toward Indole-Containing Polysubstituted Selenophenes

A novel and efficient SeCl2-mediated chalcogenative cyclization strategy toward 3-selenophen-3-yl-1 H-indoles from readily available and conveniently substituted propargyl indoles is described. It entails an unprecedented selenirenium-induced 1,2-indolyl shift prompted by the electrophilic addition of SeCl2 to the triple bond of the propargyl indole, followed by cyclization through the intermediacy of a 1-seleno-1,3-diene. The reaction takes place at room temperature and shows excellent selectivity, broad substrate scope, and wide functional group tolerance.