TY - JOUR T1 - Selective iron-catalyzed cross-coupling reactions of grignard reagents with enol triflates, acid chlorides, and dichloroarenes. AU - Scheiper,Bodo, AU - Bonnekessel,Melanie, AU - Krause,Helga, AU - Fürstner,Alois, PY - 2004/5/22/pubmed PY - 2004/5/22/medline PY - 2004/5/22/entrez SP - 3943 EP - 9 JF - The Journal of organic chemistry JO - J Org Chem VL - 69 IS - 11 N2 - Cheap, readily available, air stable, nontoxic, and environmentally benign iron salts such as Fe(acac)(3) are excellent precatalysts for the cross-coupling of Grignard reagents with alkenyl triflates and acid chlorides. Moreover, it is shown that dichloroarene and -heteroarene derivatives as the substrates can be selectively monoalkylated by this method. All cross-coupling reactions proceed very rapidly under notably mild conditions and turned out to be compatible with a variety of functional groups in both reaction partners. A detailed analysis of the preparative results suggests that iron-catalyzed C-C bond formations can occur via different pathways. Thus, it is likely that reactions of methylmagnesium halides involve iron-ate complexes as the active components, whereas reactions of Grignard reagents with two or more carbon atoms are effected by highly reduced iron-clusters of the formal composition [Fe(MgX)(2)](n) generated in situ. Control experiments using the ate-complex [Me(4)Fe]Li(2) corroborate this interpretation. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/15153029/Selective_iron_catalyzed_cross_coupling_reactions_of_grignard_reagents_with_enol_triflates_acid_chlorides_and_dichloroarenes_ DB - PRIME DP - Unbound Medicine ER -