Copper catalyzed magnesium-Barbier reaction for γ-selective alkyl-allyl coupling
CuCN catalyzed alkyl-allyl coupling under magnesium-Barbier conditions occurs regioselectively and affords predominantly the γ-products in good to high yields. This one-pot CuCN catalyzed reaction utilising Mg, an alkyl halide and an allylic substrate in THF at room temperature provides an easy alternative to the classical CuCN catalyzed γ-allylation of alkyl Grignard reagents.
Erdik, Ender,Ko?o?lu, Melike
p. 4211 - 4214
(2008/02/08)
A one-pot synthesis of ibuprofene involving three consecutive steps of superbase metalation
A one-pot reaction sequence consisting of three consecutive metalation and electrophilic substitution stages leads to 2-(4-isobutylphenyl)propanoic acid with 52% over-all yield. A crucial step is the alkylation of deprotonated p-ethyltoluene with isopropyl bromide. In general terms, sec-alkyl halides and benzyl or allyl type alkalimetal reagents undergo coupling reactions with surprising ease.
Faigl,Schlosser
p. 3369 - 3370
(2007/10/02)
THERMISCHE STABILITAET VON BIS(ALK-2-ENYL)ZINK-VERBINDUNGEN
The dialk-2-enylzinc compounds I-III react slowly at 20 to 50 deg C by addition of the Zn-C bond to the C=C bond of an alk-2-enyl group to give oligomers from which the alkenes XIII-XV are released on hydrolysis.For I-III homolytic cleavage of the Zn-Callyl bond, followed by coupling of the allyl radicals to give the alkadienes V-VII, IX and XI predominates above 50 deg C.IV decomposes mainly homolytically even at 20 deg C.
Lehmkuhl, Herbert,Doering, Ingo,Nehl, Hans
p. 7 - 12
(2007/10/02)
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