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          Institute: MPI für Kohlenforschung     Collection: Publikationen MPI für Kohlenforschung     Display Documents



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ID: 19678.0, MPI für Kohlenforschung / Publikationen MPI für Kohlenforschung
Iron-catalyzed cross-coupling reactions
Authors:Fürstner, A.; Leitner, A.; Mendéz, M.; Krause, H.
Language:English
Date of Publication (YYYY-MM-DD):2002-11-20
Title of Journal:Journal of the American Chemical Society
Journal Abbrev.:J. Am. Chem. Soc.
Volume:124
Issue / Number:46
Start Page:13856
End Page:13863
Review Status:Peer-review
Audience:Experts Only
Abstract / Description:Simple iron salts such as FeCln, 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 -CF3 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.
Comment of the Author/Creator:Date: 2002, NOV 20
External Publication Status:published
Document Type:Article
Communicated by:N. N.
Affiliations:MPI für Kohlenforschung
Identifiers:ISI:000179269800046 [ID No:1]
ISSN:0002-7863 [ID No:2]
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