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Chiral cyclometalation of 6-(1-phenylbenzyl)-2,2′-bipyridine

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Stoccoro, Sergio, Maidich, Luca, Ruiu, Tiziana, Cinellu, Maria Agostina, Clarkson, Guy J. and Zucca, Antonio (2015) Chiral cyclometalation of 6-(1-phenylbenzyl)-2,2′-bipyridine. Dalton Transactions, 44 (41). pp. 18001-18011. doi:10.1039/c5dt02483h

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Official URL: http://dx.doi.org/10.1039/C5DT02483H

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Abstract

A new bipyridine ligand, 6-(1-phenylbenzyl)-2,2′-bipyridine, has been prepared by a multistep synthesis starting from the corresponding substituted pyridine. The coordinating properties of the new ligand have been tested with two d8 metal ions, Pt(II) and Pd(II), to give the cyclometalated complexes [Pt(N,N,C)Cl] and [Pd(N,N,C)Cl], where N,N,C is a terdentate deprotonated bipyridine containing a new stereogenic carbon atom directly generated by C–H bond activation. The single-crystal of the platinum complex has been solved by X-ray diffraction. DFT calculations confirm the presence of a Pt⋯H interaction that stabilizes one of the two possible conformers by 14.7 kJ mol−1 for Pt and 12.9 kJ mol−1 for Pd. The energy barrier to pass from one conformer to the other is 25.4 and 23.8 kJ mol−1 respectively. Under different reaction conditions, regioselective activation of a pyridine C–H bond gave the less common cyclometalated rollover complex [Pt(L-H)Me(DMSO)], which was isolated and characterised.

Item Type: Journal Article
Subjects: Q Science > QC Physics
Divisions: Faculty of Science > Chemistry
Library of Congress Subject Headings (LCSH): Chirality
Journal or Publication Title: Dalton Transactions
Publisher: Royal Society of Chemistry
ISSN: 1477-9226
Official Date: 7 November 2015
Dates:
DateEvent
7 November 2015Published
18 September 2015Available
17 September 2015Accepted
Date of first compliant deposit: 18 August 2016
Volume: 44
Number: 41
Number of Pages: 11
Page Range: pp. 18001-18011
DOI: 10.1039/c5dt02483h
Status: Peer Reviewed
Publication Status: Published
Access rights to Published version: Restricted or Subscription Access

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