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Science 29 August 2008:
Vol. 321. no. 5893, pp. 1188 - 1190
DOI: 10.1126/science.1159979
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Reports

Hydrodefluorination of Perfluoroalkyl Groups Using Silylium-Carborane Catalysts

Christos Douvris and Oleg V. Ozerov*

Carbon-fluorine bonds are among the most unreactive functionalities in chemistry. Interest in their activation arises in part from the high global warming potentials of anthropogenic polyfluoroorganic compounds. Conversion to carbon-hydrogen bonds (hydrodefluorination) is the simplest modification of carbon-fluorine bonds, but efficient catalytic hydrodefluorination of perfluoroalkyl groups has been an unmet challenge. We report a class of carborane-supported, highly electrophilic silylium compounds that act as long-lived catalysts for hydrodefluorination of trifluoromethyl and nonafluorobutyl groups by widely accessible silanes under mild conditions. The reactions are completely selective for aliphatic carbon-fluorine bonds in preference to aromatic carbon-fluorine bonds.

Department of Chemistry, Brandeis University, MS 015, 415 South Street, Waltham, MA 02454, USA.

* To whom correspondence should be addressed. E-mail: ozerov{at}brandeis.edu

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THIS ARTICLE HAS BEEN CITED BY OTHER ARTICLES:
A Cryptand-Encapsulated Germanium(II) Dication.
P. A. Rupar, V. N. Staroverov, and K. M. Baines (2008)
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Science. ISSN 0036-8075 (print), 1095-9203 (online)