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

Ligand-assisted nickel-catalysed sp3–sp3 homocoupling of unactivated alkyl bromides and its application to the active template synthesis of rotaxanes
Ligand-assisted nickel-catalysed sp3–sp3 homocoupling of unactivated alkyl bromides and its application to the active template synthesis of rotaxanes
An efficient, mild and operationally simple Ni-catalysed sp3-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 ?-hydride elimination of alkyl-Ni intermediates.
1478-6524
383-386
Goldup, Stephen M.
0a93eedd-98bb-42c1-a963-e2815665e937
Leigh, David A.
826353b6-267f-44cd-a7e7-adf0c34f66c9
McBurney, Roy T.
200683de-6158-4a21-8d22-68adc26f0e59
McGonigal, Paul R.
c76f3367-e206-42ae-b433-dd5fa6473142
Plant, Andrew
40edb12b-3ef5-4a99-abbf-9171a9a3657f
Goldup, Stephen M.
0a93eedd-98bb-42c1-a963-e2815665e937
Leigh, David A.
826353b6-267f-44cd-a7e7-adf0c34f66c9
McBurney, Roy T.
200683de-6158-4a21-8d22-68adc26f0e59
McGonigal, Paul R.
c76f3367-e206-42ae-b433-dd5fa6473142
Plant, Andrew
40edb12b-3ef5-4a99-abbf-9171a9a3657f

Goldup, Stephen M., Leigh, David A., McBurney, Roy T., McGonigal, Paul R. and Plant, Andrew (2010) Ligand-assisted nickel-catalysed sp3–sp3 homocoupling of unactivated alkyl bromides and its application to the active template synthesis of rotaxanes. Chemical Science, 1 (3), 383-386. (doi:10.1039/c0sc00279h).

Record type: Article

Abstract

An efficient, mild and operationally simple Ni-catalysed sp3-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 ?-hydride elimination of alkyl-Ni intermediates.

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More information

Published date: 28 May 2010
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow

Identifiers

Local EPrints ID: 370660
URI: http://eprints.soton.ac.uk/id/eprint/370660
ISSN: 1478-6524
PURE UUID: c3584343-1242-4fe3-b8af-c1176dea358b
ORCID for Stephen M. Goldup: ORCID iD orcid.org/0000-0003-3781-0464

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Date deposited: 03 Nov 2014 13:43
Last modified: 14 Mar 2024 18:20

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Contributors

Author: David A. Leigh
Author: Roy T. McBurney
Author: Paul R. McGonigal
Author: Andrew Plant

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