Ligand-assisted nickel-catalysed sp3-sp3 homocoupling of unactivated alkyl bromides and its application to the active template synthesis of rotaxanes

Stephen M. Goldup; David A. Leigh; Roy T. McBurney; Paul R. McGonigal; Andrew Plant

doi:10.1039/c0sc00279h

Ligand-assisted nickel-catalysed sp³-sp³ homocoupling of unactivated alkyl bromides and its application to the active template synthesis of rotaxanes

Stephen M. Goldup, David A. Leigh^*, Roy T. McBurney, Paul R. McGonigal, Andrew Plant

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

99 Citations (Scopus)

Abstract

An efficient, mild and operationally simple Ni-catalysed sp ³-carbon-to-sp³-carbon homocoupling of unactivated alkyl bromides has been developed and utilised in the active metal template synthesis of an alkyl chain axle [2]rotaxane. The key to the transformation is the use of tridentate nitrogen-donor-atom (terpy or pybox derived) ligands which inhibit competing β-hydride elimination of alkyl-Ni intermediates.

Original language	English
Pages (from-to)	383-386
Number of pages	4
Journal	Chemical Science
Volume	1
Issue number	3
DOIs	https://doi.org/10.1039/c0sc00279h
Publication status	Published - 1 Sept 2010

ASJC Scopus subject areas

General Chemistry

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10.1039/c0sc00279h

Cite this

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abstract = "An efficient, mild and operationally simple Ni-catalysed sp 3-carbon-to-sp3-carbon homocoupling of unactivated alkyl bromides has been developed and utilised in the active metal template synthesis of an alkyl chain axle [2]rotaxane. The key to the transformation is the use of tridentate nitrogen-donor-atom (terpy or pybox derived) ligands which inhibit competing β-hydride elimination of alkyl-Ni intermediates.",

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AU - McGonigal, Paul R.

AU - Plant, Andrew

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N2 - An efficient, mild and operationally simple Ni-catalysed sp 3-carbon-to-sp3-carbon homocoupling of unactivated alkyl bromides has been developed and utilised in the active metal template synthesis of an alkyl chain axle [2]rotaxane. The key to the transformation is the use of tridentate nitrogen-donor-atom (terpy or pybox derived) ligands which inhibit competing β-hydride elimination of alkyl-Ni intermediates.

AB - An efficient, mild and operationally simple Ni-catalysed sp 3-carbon-to-sp3-carbon homocoupling of unactivated alkyl bromides has been developed and utilised in the active metal template synthesis of an alkyl chain axle [2]rotaxane. The key to the transformation is the use of tridentate nitrogen-donor-atom (terpy or pybox derived) ligands which inhibit competing β-hydride elimination of alkyl-Ni intermediates.

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