Net Oxidative Addition of C(sp3)-F Bonds to Iridium via Initial C-H Bond Activation

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Science  24 Jun 2011:
Vol. 332, Issue 6037, pp. 1545-1548
DOI: 10.1126/science.1200514

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Carbon-fluorine bonds are the strongest known single bonds to carbon and as a consequence can prove very hard to cleave. Alhough vinyl and aryl C-F bonds can undergo oxidative addition to transition metal complexes, this reaction has appeared inoperable with aliphatic substrates. We report the addition of C(sp3)-F bonds (including alkyl-F) to an iridium center via the initial, reversible cleavage of a C-H bond. These results suggest a distinct strategy for the development of catalysts and promoters to make and break C-F bonds, which are of strong interest in the context of both pharmaceutical and environmental chemistry.

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