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Electroreductive “Barbier Type” allylation of imines with a combination of a Pb(0)/Pb(II) redox mediator and sacrificial anode (Al)

✍ Scribed by Hideo Tanaka; Takao Nakahara; Hamid Dhimane; Sigeru Torii

Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 210 KB
Volume: 30
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)99348-1

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✦ Synopsis

An electroreductive "Barbier Type" allylation of imines with ally1 bromide has been performed in a PbBqJ3uqNBqTI-G(Al anode)-(Pt cathode) system. A combination of Pb(O)/Pb(II) redox and a sacrificial aluminum anode works as a mediator for both cathodic and anodic electron transfer processes, respectively. Recently. electroreductive "Barbier Type" allylation of carbonyl compounds in a metal-redox mediatory system has attracted much attention from mechanistic and synthetic viewpoints.1) Several metal redoxes. e.g., Sn(IV)/Sn(O or If),la) Pb(II)/Pb(O).lb) Ni(II)/Ni(O),Ic) and Bi(IlI)/Bi(O),ld) have been investigated for this purpose. Meanwhile, none is known

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Barbier-type allylation of acetals with

Barbier-type allylation of acetals with allyl bromide in a Pb/Al bimetal redox system

✍ Hideo Tanaka; Shiro Yamashita; Youichi Ikemoto; Sigeru Torii 📂 Article 📅 1988 🏛 Elsevier Science 🌐 French ⚖ 224 KB

A novel mono and/or double allylation of acetals is achieved by the action of ally1 bromide, aluminium metal, and a catalytic amount of PbBr2 and A1Br3 in tetrahydrofuran.