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Abstract:

This account is focused on highlighting the recent advances on synthetically-useful organic reactions employing siliconcentered radicals in water, and presenting new reactions in water, mediated by silyl radicals. In doing so, several types of organic radical transformations will be discussed, such as reduction of organic halides utilizing non toxic organosilane reducing agents in water, transformation of azides into amines, synthesis of protecting silyl ethers in water, hydrosilylation reactions of carbon-carbon double and triple bonds, and radical cyclization reactions in water induced by silicon-centered radicals. More recently, intermolecular radical carboncarbon bond formation reactions mediated by silyl radicals have allowed the synthesis of perfluoroalkyl-substituted compounds in water, widening the scope for the syntheses of fluorophoes. These silicon radical-mediated chain reactions in water are initiated through different methods, among which, thermal, photochemical, and dioxygen initiations are reported to be the most successful methods in water. A versatile aspect of the radical methodology employed in water will be presented in terms of dealing with water-soluble and organic solvent- soluble substrates in these silicon radical-mediated reactions in water. In this regard, for an efficient chain process to take place in water, a chain carrier must be used when water-soluble substrates are employed, whereas organic solvent-soluble materials do not require a chain transporter when silyl radicals are used in water. © 2011 Bentham Science Publishers Ltd.

Registro:

Documento: Artículo
Título:Organic synthesis in water mediated by silyl radicals
Autor:Barata-Vallejo, S.; Nudelman, N.S.; Postigo, A.
Filiación:Department of Chemistry, Faculty of Science, University of Belgrano, Villanueva 1324, CP 1426-Buenos Aires, Argentina
Sebastián Barata-Vallejo and Norma Sbarbati Nudelman, Departamento de Química Orgánica-Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón II, 3er piso, Ciudad Universitaria, 1428-Buenos Aires, Argentina
Palabras clave:Chain carrier; Radical carbon-carbon bond formation in water; Silyl radicals; Silyl radicals in water
Año:2011
Volumen:15
Número:11
Página de inicio:1826
Página de fin:1842
DOI: http://dx.doi.org/10.2174/138527211795656589
Título revista:Current Organic Chemistry
Título revista abreviado:Curr. Org. Chem.
ISSN:13852728
CODEN:CORCF
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_13852728_v15_n11_p1826_BarataVallejo

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Citas:

---------- APA ----------
Barata-Vallejo, S., Nudelman, N.S. & Postigo, A. (2011) . Organic synthesis in water mediated by silyl radicals. Current Organic Chemistry, 15(11), 1826-1842.
http://dx.doi.org/10.2174/138527211795656589
---------- CHICAGO ----------
Barata-Vallejo, S., Nudelman, N.S., Postigo, A. "Organic synthesis in water mediated by silyl radicals" . Current Organic Chemistry 15, no. 11 (2011) : 1826-1842.
http://dx.doi.org/10.2174/138527211795656589
---------- MLA ----------
Barata-Vallejo, S., Nudelman, N.S., Postigo, A. "Organic synthesis in water mediated by silyl radicals" . Current Organic Chemistry, vol. 15, no. 11, 2011, pp. 1826-1842.
http://dx.doi.org/10.2174/138527211795656589
---------- VANCOUVER ----------
Barata-Vallejo, S., Nudelman, N.S., Postigo, A. Organic synthesis in water mediated by silyl radicals. Curr. Org. Chem. 2011;15(11):1826-1842.
http://dx.doi.org/10.2174/138527211795656589