Tetrahedron Letters

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

S Usugi, H Yorimitsu, K Oshima

文献索引：Usugi, Shin-ichi; Yorimitsu, Hideki; Oshima, Koichiro Tetrahedron Letters, 2001 , vol. 42, # 27 p. 4535 - 4538

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被引用次数: 41

摘要

An allylgallium reagent is found to be effective for radical allylation of α-iodo or α-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 ...