Rearrangement of biaryl monoaminocarbenes via concerted asynchronous insertion into aromatic C-H bonds.
The biphenyl and binaphthyl diisopropylaminocarbenes were found to be only transient species that spontaneously and quantitatively rearrange into the corresponding aminofluorenes. DFT calculations confirm that these insertion reactions of aminocarbenes into proximal aromatic C-H bonds require only a moderate energy barrier and support a concerted, strongly asynchronous, mechanism dominated by C arom-->C carbene proton transfer.
Vignolle
Joan
J
Laboratoire Hétérochimie Fondamentale et Appliquée du CNRS (UMR 5069), Université Paul Sabatier, 118, route de Narbonne, 31062 Toulouse Cedex 09, France.
Asay
Matthew
M
Miqueu
Karinne
K
Bourissou
Didier
D
Bertrand
Guy
G