Issue 1, 2017

Efficient symmetrical bidentate dioxime ligand-accelerated homogeneous palladium-catalyzed Suzuki–Miyaura coupling reactions of aryl chlorides

Abstract

A series of N,O-bidentate ligands were synthesized using the Vilsmeier–Haack reaction and oximation. 2,5-Dihydroxyterephthalaldehyde dioxime (L8) as an efficient N,O-symmetrical bidentate ligand was prepared from hydroquinone. It was studied as a high activity ligand for palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of aryl chlorides with arylboronic acids under mild conditions. The coupling reactions were performed in the presence of PdCl2 as the catalyst, L8 as the ligand, Na2CO3 as the base, PEG-400 as the PTC and in ethanol/water (1 : 1) as an environmentally benign solvent at 85 °C. Plentiful biaryls were obtained by the optimized reaction with good yields at a low palladium loading of 0.20 mol%.

Graphical abstract: Efficient symmetrical bidentate dioxime ligand-accelerated homogeneous palladium-catalyzed Suzuki–Miyaura coupling reactions of aryl chlorides

Supplementary files

Article information

Article type
Paper
Submitted
08 Sep 2016
Accepted
29 Nov 2016
First published
12 Dec 2016

New J. Chem., 2017,41, 372-376

Efficient symmetrical bidentate dioxime ligand-accelerated homogeneous palladium-catalyzed Suzuki–Miyaura coupling reactions of aryl chlorides

J. Song, H. Zhao, Y. Liu, H. Han, Z. Li, W. Chu and Z. Sun, New J. Chem., 2017, 41, 372 DOI: 10.1039/C6NJ02815B

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements