Carbenes As Catalysts for Transformations of Organometallic Iron Complexes

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Science  23 Oct 2009:
Vol. 326, Issue 5952, pp. 559-562
DOI: 10.1126/science.1178919

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Compared with the enormous arsenal of catalysts used to produce organic compounds, complementary species that are able to mediate sophisticated organometallic transformations are virtually nonexistent. We found that stable N-heterocyclic carbenes (NHCs) can mediate unusual organometallic transformations in solution at room temperature. Depending on the choice of NHC initiator, stoichiometric or catalytic reactions of bis(cyclooctatetraene)iron [Fe(COT)2] ensue. The stoichiometric reaction leads to the isolation of a previously unknown mixed-valent species, featuring distinct and directly bonded Fe(0) and Fe(I) centers. In the catalytic process, three iron atoms are fused to afford the tri-iron cluster Fe3(COT)3, which is a hydrocarbon analog of Dewar’s classic Fe3(CO)12 complex. The key step in both of these processes is proposed to involve the NHC’s ability to induce metal–metal bond formation. These NHC-mediated reactions provide a foundation on which to develop future organometallic transformations that are catalyzed by organic species.

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