Barbier-type allylation of carbonyl derivatives by use of aluminum as an electron pool. Double allylation of carboxylic esters

Citation
H. Tanaka et al., Barbier-type allylation of carbonyl derivatives by use of aluminum as an electron pool. Double allylation of carboxylic esters, INORG CHIM, 296(1), 1999, pp. 204-207
Citations number
28
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Inorganic & Nuclear Chemistry
Journal title
INORGANICA CHIMICA ACTA
ISSN journal
0020-1693 → ACNP
Volume
296
Issue
1
Year of publication
1999
Pages
204 - 207
Database
ISI
SICI code
0020-1693(199912)296:1<204:BAOCDB>2.0.ZU;2-4
Abstract
Double allylation of carboxylic eaters with allyl bromide was performed suc cessfully by the action of aluminum metal and a catalytic amount of lead(II ) bromide in tetrahydrofuran (THF). The proper choice of solvent is essenti al for the reaction; thus, among the examined solvents, ethers, e.g. THF, 1 ,2-dimethoxyethane (DME), and diethyl ether, could be successfully used for the double allylation but with N,N-dimethylformamide (DMF), aqueous MeOH, and aqueous THF, no appreciable reaction occurred. Allylation of benzaldehy de dimethyl acetal and N-benzylimine in THF under the same conditions took place smoothly to afford the corresponding allylation products. In a simila r manner, allylation of benzonitrile was also performed to afford the doubl y allylated benzylamine. (C) 1999 Elsevier Science S.A, All rights reserved .