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

Zucca, Antonio, Maidich, Luca, Canu, Laura, Petretto, Giacomo L., Stoccoro, Sergio, Cinellu, Maria Agostina, Clarkson, Guy J. and Rourke, Jonathan P. 2014. Rollover‐assisted C(sp2)-C(sp3) bond formation. Chemistry - A European Journal 20 (18) , pp. 5501-5510. 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)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
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Wiley
ISSN: 0947-6539
Last Modified: 21 Jan 2019 12:46
URI: http://orca-mwe.cf.ac.uk/id/eprint/118443

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