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Structural and synthetic insights into pyridine homocouplings mediated by a beta-diketiminato magnesium amide complex

Lookup NU author(s): Emeritus Professor Bill Clegg, Dr Mike Probert

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This is the authors' accepted manuscript of an article that has been published in its final definitive form by Wiley - VCH Verlag GmbH & Co. KGaA, 2018.

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Abstract

The reaction of [(DippNacnac)Mg(TMP)] (1) with 4-subtituted pyridines proceeds via sequential regioselectivemetalation and 1,2-addition to furnish a range of symmetric4,4’-R2-2,2’-bipyridines in good yield, representing a newentry into bipyridine synthesis. Interestingly, the reactionwith of 1 with 2-OMe-pyridine led to formation of asymmetricbipyridine 6, resulting from the C6-magnesiation of theheterocycle followed by a CC coupling step by addition tothe C2 position of a second, non-metallated molecule, andsubsequent elimination of [DippNacnacMgOMe]2 (7). Synthesiscombined with spectroscopic and structural analysis help rationalisethe underlying processes resulting in the observedreactivity, and elucidates the key role of the sterically encumberedb-diketiminate ligand plays in determining regioselectivity.


Publication metadata

Author(s): Hevia E, McLellan R, Davin L, Clegg W, Kennedy AR, Probert MR

Publication type: Article

Publication status: Published

Journal: Chemistry - A European Journal

Year: 2018

Volume: 24

Issue: 55

Pages: 14830-14835

Print publication date: 01/10/2018

Online publication date: 27/07/2018

Acceptance date: 27/07/2018

ISSN (electronic): 1521-3765

Publisher: Wiley - VCH Verlag GmbH & Co. KGaA

URL: https://doi.org/10.1002/chem.201803297

DOI: 10.1002/chem.201803297


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