Copper(I)-catalyzed addition of trifluoromethylated benzyl radicals derived from aryltrifluoroethyl bromides to terminal olefins

A class of compounds with a trifluoromethyl group on a long alkyl chain were prepared via radical reaction followed by tin hydride reduction. Relatively unreactive aryltrifluoroethyl bromides were reacted with 1-octene in the presence of CuCl and 2,2′-bipyridyl at high temperatures. Trifluoromethyla...

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Bibliographic Details
Published in:Journal of fluorine chemistry 2002-03, Vol.114 (1), p.91-98
Main Authors: Okano, Takashi, Sugiura, Hirokazu, Fumoto, Masataka, Matsubara, Hiroyoshi, Kusukawa, Takahiro, Fujita, Makoto
Format: Article
Language:English
Subjects:
Atom-transfer reaction
Cu(I) catalysts
Radical addition
Tin hydride reduction
Trifluoromethyl compound
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Summary:A class of compounds with a trifluoromethyl group on a long alkyl chain were prepared via radical reaction followed by tin hydride reduction. Relatively unreactive aryltrifluoroethyl bromides were reacted with 1-octene in the presence of CuCl and 2,2′-bipyridyl at high temperatures. Trifluoromethylated benzyl radical was generated, and a diastereomer mixture of radical adducts was obtained with a (60–70):(40–30) diastereomer ratio. Ph3SnH reduction of the adducts gave the corresponding hydrocarbons with an isolated trifluoromethyl group. The reactions with styrene or aromatic and aliphatic silyl enol ethers led to the formation of trifluorodiphenylbutene and β-trifluoromethylated ketones, respectively.
ISSN:0022-1139
1873-3328
DOI:10.1016/S0022-1139(02)00002-7