Triethylborane-induced radical allylation of alpha-halo carbonyl compoundswith allylgallium reagent in aqueous media

Authors
Usugi, S Yorimitsu, H Oshima, K
Citation
S. Usugi et al., Triethylborane-induced radical allylation of alpha-halo carbonyl compoundswith allylgallium reagent in aqueous media, TETRAHEDR L, 42(27), 2001, pp. 4535-4538
Citations number
36
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
27
Year of publication
2001
Pages
4535 - 4538
Database
ISI
SICI code
0040-4039(20010702)42:27<4535:TRAOAC>2.0.ZU;2-O
Abstract
An allylgallium reagent is found to be effective for radical allylation of alpha -iodo or alpha -bromo carbonyl compounds. Treatment of benzyl bromoac etate with allylgallium, prepared from allylmagnesium chloride and gallium trichloride, in the presence of triethylborane in THF provided benzyl 4-pen tenoate in good yield. The addition of water as a cosolvent improved the yi elds of allylated products. It was revealed that the allylgallium species r esists immediate decomposition on exposure to water. (C) 2001 Elsevier Scie nce Ltd. All rights reserved.