title: Iron-catalyzed cross-coupling reactions.
abstract: Simple iron salts such as FeCl(n), Fe(acac)(n) (n = 2,3) or the salen complex 4 turned out to be highly efficient, cheap, toxicologically benign, and environmentally friendly precatalysts for a host of cross-coupling reactions of alkyl or aryl Grignard reagents, zincates, or organomanganese species with aryl and heteroaryl chlorides, triflates, and even tosylates. An "inorganic Grignard reagent" of the formal composition [Fe(MgX)(2)] prepared in situ likely constitutes the propagating species responsible for the catalytic turnover, which occurs in many cases at an unprecedented rate even at or below room temperature. Because of the exceptionally mild reaction conditions, a series of functional groups such as esters, ethers, nitriles, sulfonates, sulfonamides, thioethers, acetals, alkynes, and -CF(3) groups are compatible. The method also allows for consecutive cross-coupling processes in one pot, as exemplified by the efficient preparation of compound 12, and has been applied to the first synthesis of the cytotoxic marine natural product montipyridine 8. In contrast to the clean reaction of (hetero)aryl chlorides, the corresponding bromides and iodides are prone to a reduction of their C-X bonds in the presence of the iron catalyst.
authors.affiliation: Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim/Ruhr, Germany. fuerstner@mpi-muelheim.mpg.de
authors.forename: Alois
authors.initials: A
authors.lastname: Fürstner
authors.forename: Andreas
authors.initials: A
authors.lastname: Leitner
authors.forename: María
authors.initials: M
authors.lastname: Méndez
authors.forename: Helga
authors.initials: H
authors.lastname: Krause
mesh_terms: D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D007501:Iron / Q000737:chemistry*; D058085:Iron Compounds / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*
chemical_list: D058085:Iron Compounds; D009942:Organometallic Compounds; D007501:Iron