G. Cahiez et S. Marquais, HIGHLY CHEMOSELECTIVE AND STEREOSELECTIVE FE-CATALYZED ALKENYLATION OF ORGANOMANGANESE REAGENTS, Tetrahedron letters, 37(11), 1996, pp. 1773-1776
Organomanganese chlorides react with alkenyl iodides, bromides and chl
orides in the presence of 3% Fe(acac)(3). The reaction takes place und
er very mild conditions (THF-NMP, rt, 1h) to afford the substituted ol
efin in excellent yields with a high stereo- and chemoselectivity. Thu
s an unprotected keto alkenyl chloride selectively gives the correspon
ding keto olefin. From a preparative point of view, this procedure is
the first real alternative to the Pd- and Ni-cross coupling reaction u
sed until now.