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Triethylborane-induced radical allylation of α-halo carbonyl compounds with allylgallium reagent in aqueous media

✍ Scribed by Shin-ichi Usugi; Hideki Yorimitsu; Koichiro Oshima

Book ID: 104230880
Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 65 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)00815-2

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✦ Synopsis

An allylgallium reagent is found to be effective for radical allylation of a-iodo or a-bromo carbonyl compounds. Treatment of benzyl bromoacetate with allylgallium, prepared from allylmagnesium chloride and gallium trichloride, in the presence of triethylborane in THF provided benzyl 4-pentenoate in good yield. The addition of water as a cosolvent improved the yields of allylated products. It was revealed that the allylgallium species resists immediate decomposition on exposure to water.

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