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Facile and Regioselective C–H Bond Activation of Aromatic Substrates by an Fe(II) Complex Involving a Spin-Forbidden Pathway

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posted on 25.03.2013 by Steven E. Kalman, Alban Petit, T. Brent Gunnoe, Daniel H. Ess, Thomas R. Cundari, Michal Sabat
The Fe­(II) complex Cp*Fe­(CO)­(NCMe)­Ph (Cp* = η5-pentamethylcyclopentadienyl) is shown to mediate facile and highly regioselective C–H activation of aromatic substrates including benzene, furan, thiophene, thiazole, and 2-methylfuran. Experimental and computational evidence suggest a mechanism for C–H activation that involves NCMe dissociation, multiple spin intersystem crossings, C–H bond coordination, and C–H bond cleavage by a σ-bond metathesis reaction.