Cyclometallation of 2-(1-naphthyl)-pyridine is described. While cyclopalladation results in a five-membered metallacycle, cycloauration displays a completely orthogonal regioselectivity, resulting in the six-membered ring analogue. Bromination of the gold metallacycle results in the new C–H functionalisation product 2-(8-bromonaphth-1-yl)pyridine.
M. Kondrashov, S. Raman and O. F. Wendt, Chem. Commun., 2015, 51, 911 DOI: 10.1039/C4CC07962K
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