A SeCl2-Mediated Approach Toward Indole-Containing Polysubstituted Selenophenes

MARTINS, GUILHERME M.; SILVEIRA, CLAUDIO; KAUFMAN, TEODORO S.; BACK, DAVI FERNANDO

JOURNAL OF ORGANIC CHEMISTRY

AMER CHEMICAL SOC

Lugar: Washington; Año: 2018

0022-3263

A novel and efficient SeCl2-mediatedchalcogenative cyclization strategy toward 3-selenophen-3-yl-1H-indoles from readily available andconveniently substituted propargyl indoles, is described. It entails anunprecedented selenirenium-induced 1,2-indolyl shift prompted by theelectrophilic addition of SeCl2 to the triple bond of the propargylindole, followed by cyclization through the intermediacy of a1-seleno-1,3-diene. The reaction takes place at room temperature, showsexcellent selectivity, broad substrate scope and wide functional grouptolerance.