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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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.
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