PHOTOCATALYTIC FLUOROALKYLATION REACTIONS OF ORGANIC COMPOUNDS

YERIEN DAMIAN; BARATA VALLEJO, SEBASTIAN; BONESI S. M.; POSTIGO J. ALBERTO

ORGANIC & BIOMOLECULAR CHEMISTRY

ROYAL SOC CHEMISTRY

Lugar: CAMBRIDGE-DOI: 10.1039/C5OB01486G; Año: 2015 vol. 13 p. 11153 - 11183

1477-0520

DOI: 10.1039/C5OB01486GPhotocatalytic methods for fluoroalkyl-radical generation provide more convenientalternatives to the classical perfluoroalkyl-radical (Rf) production through chemicalinitiators, such as azo or peroxide compounds or the employment of transition metalsthrough thermal electron transfer (ET) initiation process. The mild photocatalytic reactionconditions tolerate a variety of functional groups and, thus, are handy to the late-stagemodification of bioactive molecules. Transition metal-photocatalytic reactions for Rfradical generation profit from the redox properties of coordinatively saturated Ru or Irorganocomplexes to act as both electron donor and reductive species, thus allowing for theutilization of electron accepting and donating fluoroalkylating agents for Rf radicalproduction. On the other hand, laboratory-available and inexpensive photoorgano catalysts(POC), in the absence of transition metals, can also act as electron exchange species uponexcitation, resulting in ET reactions that produce Rf radicals. In this work, a critical accountof transition metal, and transition metal-free Rf radical production will be described withphotoorgano catalysts, studying classical examples and the most recent investigations in thefield.