Issue 68, 2012

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

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

Supplementary files

Article information

Article type
Communication
Submitted
26 Apr 2012
Accepted
06 Jul 2012
First published
06 Jul 2012

Chem. Commun., 2012,48, 8553-8555

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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