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Rollover-Assisted C(sp2)C(sp3) Bond Formation

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Zucca, Antonio, Maidich, Luca, Canu, Laura, Petretto, Giacomo L., Stoccoro, Sergio, Cinellu, Maria Agostina, Clarkson, Guy J. and Rourke, Jonathan (2014) Rollover-Assisted C(sp2)C(sp3) Bond Formation. Chemistry - A European Journal, 20 (18). pp. 5501-5510. doi:10.1002/chem.201304257

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Official URL: http://dx.doi.org/10.1002/chem.201304257

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Abstract

Rollover cyclometalation involves bidentate heterocyclic donors, unusually acting as cyclometalated ligands. The resulting products, possessing a free donor atom, react differently from the classical cyclometalated complexes. Taking advantage of a “rollover”/“retro-rollover” reaction sequence, a succession of oxidative addition and reductive elimination in a series of platinum(II) complexes [Pt(N,C)(Me)(PR3)] resulted in a rare C(sp2)[BOND]C(sp3) bond formation to give the bidentate nitrogen ligands 3-methyl-2,2′-bipyridine, 3,6-dimethyl-2,2′-bipyridine, and 3-methyl-2-(2′-pyridyl)-quinoline, which were isolated and characterized. The nature of the phosphane PR3 is essential to the outcome of the reaction. This route constitutes a new method for the activation and functionalization of C[BOND]H bond in the C(3) position of bidentate heterocyclic compounds, a position usually difficult to functionalize.

Item Type: Journal Article
Divisions: Faculty of Science > Chemistry
Journal or Publication Title: Chemistry - A European Journal
Publisher: Wiley - V C H Verlag GmbH & Co. KGaA
ISSN: 0947-6539
Official Date: 28 March 2014
Dates:
DateEvent
28 March 2014Available
31 October 2013Submitted
Volume: 20
Number: 18
Page Range: pp. 5501-5510
DOI: 10.1002/chem.201304257
Status: Peer Reviewed
Publication Status: Published
Access rights to Published version: Restricted or Subscription Access

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