For a variety of organometallic catalytic processes, including Suzuki-Miyaura cross coupling, the oxidative addition of aryl and alkyl halides is a key intermediate step. The two-electron oxidative addition of both aryl and alkyl halides to neutral iron compounds, however, has little precedent. The aryl-substituted bis(imidazol-2-ylidene)pyridine iron dinitrogen complex (3,5-Me2MesCNC)Fe(N2)2 (3,5-Me2MesCNC = 2,6-(2,4,6-Me3-C6H2-imidazol-2-ylidene)2-3,5-Me2-pyridine) reacts rapidly with non-coordinating aryl and alkyl halides (R–X) at room temperature to give the corresponding oxidative addition products, (3,5-Me2MesCNC)Fe(R)(X)(N2), in good yields (70 – 80%). Competition experiments between the aryl halides are consistent with the order of halide reactivity I &gt; Br &gt; Cl, and mechanistic studies are consistent with a concerted oxidative addition pathway. Further reactivity of the (3,5-Me2MesCNC)Fe(R)(X)(N2) products such as transmetallation with neutral boron electrophiles and C–C bond forming reductive elimination will also be discussed.

Strong-field CNC ligands enable two-electron oxidative addition to iron(0)

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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