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Rollover-assisted C(sp2)-C(sp3) bond formation

Zucca, Antonio and Maidich, Luca and Canu, Laura and Petretto, Giacomo Luigi and Stoccoro, Sergio and Cinellu, Maria Agostina and Clarkson, Guy J. and Rourke, Jonathan P. (2014) Rollover-assisted C(sp2)-C(sp3) bond formation. Chemistry: a European Journal, Vol. 20 (18), p. 5501-5510. ISSN 0947-6539. Article.

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DOI: 10.1002/chem.201304257


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)—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—H bond in the C(3) position of bidentate heterocyclic compounds, a position usually difficult to functionalize.

Item Type:Article
ID Code:10235
Uncontrolled Keywords:Bond coupling, NMR spectroscopy, platinum, reductive elimination, rollover cyclometalation
Subjects:Area 03 - Scienze chimiche > CHIM/03 Chimica generale e inorganica
Divisions:001 Università di Sassari > 01-a Nuovi Dipartimenti dal 2012 > Chimica e Farmacia
Deposited On:29 Oct 2014 14:58

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