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

Gavin J. Harkness; Matthew L. Clarke

doi:10.1039/C7CY01205E

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.

Original language	English
Pages (from-to)	328-334
Journal	Catalysis Science & Technology
Volume	8
Issue number	1
Early online date	1 Dec 2017
DOIs	https://doi.org/10.1039/C7CY01205E
Publication status	Published - 7 Jan 2018

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Clarke_2017_CST_LessHinderedLigands_AAM
© 2017 the Authors. This work has been made available online in accordance with the publisher’s policies. This is the author created accepted version manuscript following peer review and as such may differ slightly from the final published version. The final published version of this work is available at: https://doi.org/ 10.1039/C7CY01205E
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title = "Less hindered ligands give improved catalysts for the nickel catalysed Grignard cross-coupling of aromatic ethers",

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.",

author = "Harkness, \{Gavin J.\} and Clarke, \{Matthew L.\}",

note = "The authors thanks the EPSRC for funding in the initial stages of this work from EP/J018139/1 and from the DTG.",

year = "2018",

month = jan,

day = "7",

doi = "10.1039/C7CY01205E",

language = "English",

volume = "8",

pages = "328--334",

journal = "Catalysis Science \& Technology",

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publisher = "Royal Society of Chemistry",

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T1 - Less hindered ligands give improved catalysts for the nickel catalysed Grignard cross-coupling of aromatic ethers

AU - Harkness, Gavin J.

AU - Clarke, Matthew L.

N1 - The authors thanks the EPSRC for funding in the initial stages of this work from EP/J018139/1 and from the DTG.

PY - 2018/1/7

Y1 - 2018/1/7

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/85040160788

U2 - 10.1039/C7CY01205E

DO - 10.1039/C7CY01205E

M3 - Article

SN - 2044-4753

VL - 8

SP - 328

EP - 334

JO - Catalysis Science & Technology

JF - Catalysis Science & Technology

IS - 1

ER -

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

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