Issue 17, 2019

Fluoroalkenylation of boronic acids via an oxidative Heck reaction

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

Supplementary files

Article information

Article type
Paper
Submitted
11 Feb 2019
Accepted
04 Eph 2019
First published
04 Eph 2019

Org. Biomol. Chem., 2019,17, 4317-4325

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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