(Me₃Si)₃SiH-Mediated Intermolecular Radical Perfluoroalkylation Reactions of Olefins in Water

Sebastián Barata-Vallejo and Al Postigo*

*Faculty of Science, University of Belgrano, Villanueva 1324 CP 1426-Buenos Aires, Argentina, Email: alberto.postigoub.edu.ar

S. Barata-Vallejo, A. Postigo, J. Org. Chem., 2010, 75, 6141-6148.

DOI: 10.1021/jo100901z

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Abstract

Intermolecular addition of perfluoroalkyl radicals on electron rich alkenes and alkenes with electron withdrawing groups in water, mediated by silyl radicals gives perfluoroalkyl-substituted compounds in good yields. The radical triggering events employed consist of thermal decomposition of 1,1′-azobis(cyclohexanecarbonitrile) (ACCN) or dioxygen initiation.

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Key Words

Perfluoroalkylation, Green Chemistry, TTMSS

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ID: J42-Y2010-2440