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Nickel-catalyzed fluoroethylation of arylboronic acids via Suzuki-type coupling

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Abstract

A mild method for efficient access to fluoroethylated (hetero)arenes via Suzuki-type coupling has been developed. This base metal Ni-catalyzed method features selective transformation of the more susceptible C–X bond of 1-fluoro-2-haloethanes (FCH2CH2X, X = I or Br) and leaves the vicinal fluorine intact. Preliminary mechanistic studies illustrate the intermediacy of fluoroethyl radicals in the radical-rebound oxidative addition and Ni–B transmetalation as the rate-limiting step within the catalytic cycle. The practical value of this protocol is further demonstrated by late-stage modification of several complex bioactive molecules.

Graphical abstract: Nickel-catalyzed fluoroethylation of arylboronic acids via Suzuki-type coupling

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Publication details

The article was received on 15 Jan 2019, accepted on 13 Mar 2019 and first published on 14 Mar 2019


Article type: Research Article
DOI: 10.1039/C9QO00066F
Citation: Org. Chem. Front., 2019, Advance Article

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    Nickel-catalyzed fluoroethylation of arylboronic acids via Suzuki-type coupling

    Y. Yang, J. Cai, G. Luo, Y. Jiang, Y. Su, Y. Su, C. Li, Y. Zheng, J. Zeng and Y. Liu, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00066F

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