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Issue 17, 2019
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Fluoroalkenylation of boronic acids via an oxidative Heck reaction

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Abstract

A fluoroalkenylation of boronic acids with fluoroalkyl alkenes has been developed. The Pd-catalyzed oxidative Heck coupling reaction proceeds under an oxygen atmosphere at room temperature, in the absence of a base and/or a ligand, showing excellent practicality of the process. This simple transformation is highly stereoselective to provide only E-isomers. In addition to the general approach using alkenes with functionalized fluoroalkyl reagents, this method, by transferring an aromatic system to the electron-deficient fluoroalkyl alkene, provides an efficient alternative method to yield valuable organofluorines.

Graphical abstract: Fluoroalkenylation of boronic acids via an oxidative Heck reaction

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Publication details

The article was received on 11 Feb 2019, accepted on 04 Apr 2019 and first published on 04 Apr 2019


Article type: Paper
DOI: 10.1039/C9OB00332K
Citation: Org. Biomol. Chem., 2019,17, 4317-4325

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    Fluoroalkenylation of boronic acids via an oxidative Heck reaction

    D. S. Lee and E. J. Cho, Org. Biomol. Chem., 2019, 17, 4317
    DOI: 10.1039/C9OB00332K

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