Functionalized arylzinc compounds in ethereal solvent: direct synthesis from aryl iodides and zinc powder and application to Pd-catalyzed reaction with allylic halides.
Arylzinc compounds, ArZnX, were conveniently prepared in high yields by the reaction of zinc powder with aryl iodides, which contain electron-withdrawing groups such as CO(2)CH(3), CN, Br, or CF(3) at the ortho-, meta- or para-position, or electron-donating groups such as CH(3), OCH(3), or H, at 70 degrees C in THF, at 100 degrees C, or at 130 degrees C in diglyme, respectively. Pd(dba)(2) exhibited an outstanding efficient catalytic effect for the cross-coupling of these ethereal solutions of ArZnX with allylic halides to afford a variety of functionalized allylbenzenes in high yields; the reactions were mostly carried out at 0 degrees C for 5-30 min in the presence of 5 mol % of catalyst. The conversion of the aryl iodides to allylbenzenes via two reactions could be accomplished in one pot.
Ikegami
Ryo
R
Department of Chemistry, Faculty of Science, Okayama Univesity, Tsushima, Okayama 700-8530, Japan.
Koresawa
Akiko
A
Shibata
Takanori
T
Takagi
Kentaro
K