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Abstract:

Photocatalytic methods for fluoroalkyl-radical generation provide more convenient alternatives to the classical perfluoroalkyl-radical (Rf) production through chemical initiators, such as azo or peroxide compounds or the employment of transition metals through a thermal electron transfer (ET) initiation process. The mild photocatalytic reaction conditions tolerate a variety of functional groups and, thus, are handy to the late-stage modification of bioactive molecules. Transition metal-photocatalytic reactions for Rf radical generation profit from the redox properties of coordinatively saturated Ru or Ir organocomplexes to act as both electron donor and reductive species, thus allowing for the utilization of electron accepting and donating fluoroalkylating agents for Rf radical production. On the other hand, laboratory-available and inexpensive photoorgano catalysts (POC), in the absence of transition metals, can also act as electron exchange species upon excitation, resulting in ET reactions that produce Rf radicals. In this work, a critical account of transition metal and transition metal-free Rf radical production will be described with photoorgano catalysts, studying classical examples and the most recent investigations in the field. © The Royal Society of Chemistry.

Registro:

Documento: Artículo
Título:Photocatalytic fluoroalkylation reactions of organic compounds
Autor:Barata-Vallejo, S.; Bonesi, S.M.; Postigo, A.
Filiación:Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 954 CP 1113Buenos Aires, Argentina
Departamento de Química Orgánica, CIHIDECAR-CONICET, Ciudad Universitaria, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón II, 3er pisoBuenos Aires 1428, Argentina
Palabras clave:Catalysts; Chemical compounds; Electrons; Free radical reactions; Initiators (chemical); Iridium; Metals; Redox reactions; Ruthenium; Thermionic emission; Bioactive molecules; Convenient alternatives; Initiation process; Perfluoroalkyl radicals; Photocatalytic methods; Photocatalytic reactions; Radical generation; Radical production; Transition metals; alkylating agent; coordination compound; free radical; iridium; ruthenium; transition element; alkylation; catalysis; chemistry; halogenation; light; oxidation reduction reaction; photochemistry; Alkylating Agents; Alkylation; Catalysis; Coordination Complexes; Free Radicals; Halogenation; Iridium; Light; Oxidation-Reduction; Photochemical Processes; Ruthenium; Transition Elements
Año:2015
Volumen:13
Número:46
Página de inicio:11153
Página de fin:11183
DOI: http://dx.doi.org/10.1039/c5ob01486g
Título revista:Organic and Biomolecular Chemistry
Título revista abreviado:Org. Biomol. Chem.
ISSN:14770520
CODEN:OBCRA
CAS:iridium, 13967-67-4, 7439-88-5; ruthenium, 7440-18-8; Alkylating Agents; Coordination Complexes; Free Radicals; Iridium; Ruthenium; Transition Elements
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v13_n46_p11153_BarataVallejo

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Citas:

---------- APA ----------
Barata-Vallejo, S., Bonesi, S.M. & Postigo, A. (2015) . Photocatalytic fluoroalkylation reactions of organic compounds. Organic and Biomolecular Chemistry, 13(46), 11153-11183.
http://dx.doi.org/10.1039/c5ob01486g
---------- CHICAGO ----------
Barata-Vallejo, S., Bonesi, S.M., Postigo, A. "Photocatalytic fluoroalkylation reactions of organic compounds" . Organic and Biomolecular Chemistry 13, no. 46 (2015) : 11153-11183.
http://dx.doi.org/10.1039/c5ob01486g
---------- MLA ----------
Barata-Vallejo, S., Bonesi, S.M., Postigo, A. "Photocatalytic fluoroalkylation reactions of organic compounds" . Organic and Biomolecular Chemistry, vol. 13, no. 46, 2015, pp. 11153-11183.
http://dx.doi.org/10.1039/c5ob01486g
---------- VANCOUVER ----------
Barata-Vallejo, S., Bonesi, S.M., Postigo, A. Photocatalytic fluoroalkylation reactions of organic compounds. Org. Biomol. Chem. 2015;13(46):11153-11183.
http://dx.doi.org/10.1039/c5ob01486g