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Issue 68, 2012
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Synthesis of unsymmetrical biaryl ethers through nickel-promoted coupling of polyfluoroarenes with arylboronic acids and oxygen

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Abstract

Polyfluoro-substituted unsymmetrical biaryl ethers were synthesized via a novel Ni-catalyzed cross-coupling reaction of polyfluoroarenes with arylboronic acids and oxygen. The polyfluorinated arenes presumably captured the phenoxide intermediate efficiently, which made the oxygen-insertion proceed smoothly via the SNAr protocol. The 18O labeling experiment demonstrated that the oxygen introduced into unsymmetrical diaryl ether originated from very trace amounts of oxygen in the reaction system. A plausible mechanism was also suggested.

Graphical abstract: Synthesis of unsymmetrical biaryl ethers through nickel-promoted coupling of polyfluoroarenes with arylboronic acids and oxygen

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Publication details

The article was received on 26 Apr 2012, accepted on 06 Jul 2012, published on 06 Jul 2012 and first published online on 06 Jul 2012


Article type: Communication
DOI: 10.1039/C2CC33755J
Citation: Chem. Commun., 2012,48, 8553-8555
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    Synthesis of unsymmetrical biaryl ethers through nickel-promoted coupling of polyfluoroarenes with arylboronic acids and oxygen

    J. Zhang, J. Wu, Y. Xiong and S. Cao, Chem. Commun., 2012, 48, 8553
    DOI: 10.1039/C2CC33755J

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