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Less hindered ligands give improved catalysts for the nickel catalysed Grignard cross-coupling of aromatic ethers

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Abstract

The challenging reaction of unactivated ortho-substituted aromatic ethers with Grignard reagents has been found to be most effectively catalysed using nickel complexes of less sterically hindered ligands. Air stable, cheap, commercially available [NiCl2(PnBu3)2] stands out as an improved catalyst for this type of transformation. The improved results with this catalyst even extend to some couplings of a more activated substrate when examined at higher temperatures and at catalyst loadings down to 0.1 mol%. Unusual induction periods in these latter reactions have been related to the by-product magnesium salts acting as co-catalysts.

Graphical abstract: Less hindered ligands give improved catalysts for the nickel catalysed Grignard cross-coupling of aromatic ethers

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Publication details

The article was received on 15 Jun 2017, accepted on 22 Nov 2017 and first published on 01 Dec 2017


Article type: Paper
DOI: 10.1039/C7CY01205E
Citation: Catal. Sci. Technol., 2018, Advance Article
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    Less hindered ligands give improved catalysts for the nickel catalysed Grignard cross-coupling of aromatic ethers

    G. J. Harkness and M. L. Clarke, Catal. Sci. Technol., 2018, Advance Article , DOI: 10.1039/C7CY01205E

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