Journal
DALTON TRANSACTIONS
Volume 40, Issue 4, Pages 933-943Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c0dt01239d
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Funding
- Memorial University of Newfoundland
- Natural Sciences and Engineering Research Council (NSERC) of Canada
- Canada Foundation for Innovation (CFI)
- Government of Newfoundland and Labrador
- CFI Leaders Opportunity Fund
- NSERC Research Tools and Instruments
- Newfoundland Research Development Corporation
- Memorial University of Newfoundland School of Graduate Studies
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Reaction of n-propylamino-N, N-bis(2-methylene-4-tert-butyl-6-methylphenol), H(2)L1, n-propylamino-N, N-bis(2-methylene-4,6-di-tert-butylphenol), H(2)L2, and benzylamino-N,N-bis(2-methylene-4-tert-butyl-6-methylphenol), H(2)L3, with anhydrous ferric chloride in the presence of base yields the products, [FeL1(m-Cl)](2) (1), [FeL2(mu-Cl)](2) (2) and [FeL3(mu-Cl)](2) (3). In the solid state, these complexes exist as chloride-bridged dimers giving distorted trigonal bipyramidal iron(III) ions. Reaction of H(2)L1 with FeBr3, however, results in the formation of a tetrahedral iron(III) complex possessing two bromide ligands. The amine-bis(phenolate) ligand is bidentate in this complex and bonds to the iron(III) ion via the phenolate O-donors. The central amine donor is protonated, resulting in a quaternized ammonium fragment and the iron(III) centre possesses a negative formal charge. As a result, this complex is zwitterionic and formulated as FeBr(2)L1H (4). Complex 1 is an air-stable, non-hygroscopic, single-component catalyst for C-C cross-coupling of aryl Grignard reagents with primary and secondary alkyl halides, including chlorides. Good to excellent yields of cross-coupled products are obtained in diethyl ether at room temperature. In some cases where low yields are obtained under these conditions, the use of microwave-assisted heating of the reaction mixture can improve yields.
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