Electron-catalyzed radical perfluoroalkylation of organic sulfides: The serendipitous use of the TMEDA/I2 complex as a radical initiator

Yerien, Damián Emilio
Barata Vallejo, Sebastian
Camps, B.
Cristófalo, Alejandro Ezequiel
Cano, María Emilia
Uhrig, Maria Laura
Postigo, Jose Alberto

Open link

Publication date

June 2017

DOI

10.1039/C7CY00236J

Publisher

Royal Society of Chemistry (RSC)

ISSN

2044-4753

Journal

Catalysis Science & Technology

Citation count (estimate)

Abstract

Radical initiation for the perfluoroalkylation reaction of sulfides has been performed using the complex [(TMEDA)I·I3] and visible light. This methodology bypasses the use of metal(organo)catalysts where the complex [(TMEDA)I·I3] acts as a good electron donor/reductant radical initiating agent. Biologically relevant sulfides are easily substituted with RF moieties employing a mild and environmentally benign radical strategy starting from readily available RFI.Fil: Yerien, Damián Emilio. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquímica. Departamento de Química Orgánica; ArgentinaFil: Barata Vallejo, Sebastian. Consejo Nacional de Investigaciones Científicas ...