A Convenient Wittig-Horner Mediated Synthesis of 3-Vinylsulfide Derivatives of Indoles

BRITES, NATHAN P.; SCHUMACHER, R. F.; KAUFMAN, T. S.; SILVEIRA, C. C.

ChemistrySelect

Wiley

Año: 2022 vol. 7 p. 20220135 - 20220135

A simple and robust coupling protocol is reported to providethe previously unknown indole derivatives carrying vinylsulfidemotifs attached to C􀀀 3 of the heterocycle. The developedstrategy involved a Wittig-Horner reaction with differentphosphinoxide derivatives. The reaction conditions were optimizedand its scope and limitations were assessed. The targetcompounds, including 3-arylvinylsulfides as well as symmetricand dissymmetric bis-vinylsulfides, were obtained in a straightforwardway, as mixtures of geometric isomers, in good toexcellent yields.