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

Hideo Tanaka, Sigeru Nakahata, Hiroshi Watanabe, Jinfeng Zhao, Manabu Kuroboshi, Sigeru Torii

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Double allylation of carboxylic esters with allyl bromide was performed successfully by the action of aluminum metal and a catalytic amount of lead(II) bromide in tetrahydrofuran (THF). The proper choice of solvent is essential 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 benzaldehyde dimethyl acetal and N-benzylimine in THF under the same conditions took place smoothly to afford the corresponding allylation products. In a similar manner, allylation of benzonitrile was also performed to afford the doubly allylated benzylamine.

Original languageEnglish
Pages (from-to)204-207
Number of pages4
JournalInorganica Chimica Acta
Volume296
Issue number1
Publication statusPublished - Dec 15 1999

Fingerprint

Allylation
tetrahydrofuran
Aluminum
esters
Esters
Electrons
Derivatives
aluminum
bromides
electrons
Ethers
acetals
Dimethylformamide
diethyl ether
Ether
ethers
Bromides
Metals
Lead
products

Keywords

  • Allylation
  • Aluminum metal
  • Barbier-type allylation
  • Double allylation of carboxylic ester
  • Lead(II) salts

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry

Cite this

Barbier-type allylation of carbonyl derivatives by use of aluminum as an electron pool. Double allylation of carboxylic esters. / Tanaka, Hideo; Nakahata, Sigeru; Watanabe, Hiroshi; Zhao, Jinfeng; Kuroboshi, Manabu; Torii, Sigeru.

In: Inorganica Chimica Acta, Vol. 296, No. 1, 15.12.1999, p. 204-207.

Research output: Contribution to journalArticle

Tanaka, Hideo ; Nakahata, Sigeru ; Watanabe, Hiroshi ; Zhao, Jinfeng ; Kuroboshi, Manabu ; Torii, Sigeru. / Barbier-type allylation of carbonyl derivatives by use of aluminum as an electron pool. Double allylation of carboxylic esters. In: Inorganica Chimica Acta. 1999 ; Vol. 296, No. 1. pp. 204-207.
@article{1be14faed41c4451b14b11b13ba51ac1,
title = "Barbier-type allylation of carbonyl derivatives by use of aluminum as an electron pool. Double allylation of carboxylic esters",
abstract = "Double allylation of carboxylic esters with allyl bromide was performed successfully by the action of aluminum metal and a catalytic amount of lead(II) bromide in tetrahydrofuran (THF). The proper choice of solvent is essential 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 benzaldehyde dimethyl acetal and N-benzylimine in THF under the same conditions took place smoothly to afford the corresponding allylation products. In a similar manner, allylation of benzonitrile was also performed to afford the doubly allylated benzylamine.",
keywords = "Allylation, Aluminum metal, Barbier-type allylation, Double allylation of carboxylic ester, Lead(II) salts",
author = "Hideo Tanaka and Sigeru Nakahata and Hiroshi Watanabe and Jinfeng Zhao and Manabu Kuroboshi and Sigeru Torii",
year = "1999",
month = "12",
day = "15",
language = "English",
volume = "296",
pages = "204--207",
journal = "Inorganica Chimica Acta",
issn = "0020-1693",
publisher = "Elsevier BV",
number = "1",

}

TY - JOUR

T1 - Barbier-type allylation of carbonyl derivatives by use of aluminum as an electron pool. Double allylation of carboxylic esters

AU - Tanaka, Hideo

AU - Nakahata, Sigeru

AU - Watanabe, Hiroshi

AU - Zhao, Jinfeng

AU - Kuroboshi, Manabu

AU - Torii, Sigeru

PY - 1999/12/15

Y1 - 1999/12/15

N2 - Double allylation of carboxylic esters with allyl bromide was performed successfully by the action of aluminum metal and a catalytic amount of lead(II) bromide in tetrahydrofuran (THF). The proper choice of solvent is essential 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 benzaldehyde dimethyl acetal and N-benzylimine in THF under the same conditions took place smoothly to afford the corresponding allylation products. In a similar manner, allylation of benzonitrile was also performed to afford the doubly allylated benzylamine.

AB - Double allylation of carboxylic esters with allyl bromide was performed successfully by the action of aluminum metal and a catalytic amount of lead(II) bromide in tetrahydrofuran (THF). The proper choice of solvent is essential 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 benzaldehyde dimethyl acetal and N-benzylimine in THF under the same conditions took place smoothly to afford the corresponding allylation products. In a similar manner, allylation of benzonitrile was also performed to afford the doubly allylated benzylamine.

KW - Allylation

KW - Aluminum metal

KW - Barbier-type allylation

KW - Double allylation of carboxylic ester

KW - Lead(II) salts

UR - http://www.scopus.com/inward/record.url?scp=0001589605&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0001589605&partnerID=8YFLogxK

M3 - Article

VL - 296

SP - 204

EP - 207

JO - Inorganica Chimica Acta

JF - Inorganica Chimica Acta

SN - 0020-1693

IS - 1

ER -