title: Regioselective ortho lithiation of 3-aryl and 3-styryl furans.
abstract: [structure: see text]. An unusual regioselectivity pattern for the ortho lithiation of 3-aryl and 3-styryl furans has been uncovered wherein lithiation occurs preferentially at the sterically encumbered 2-position. The results are attributed, at least in part, to stabilization of the intermediate furyl anion by through-space donation of pi-electron density from the substituent appended at the 3-position to the lithium cation. This ortho lithiation reaction may be applied as a useful synthetic tool for accessing 2,3-disubstituted furans.
authors: Department of Chemistry, University of Crete, Greece.
authors: Maria
authors: M
authors: Tofi
authors: Thomas
authors: T
authors: Georgiou
authors: Tamsyn
authors: T
authors: Montagnon
authors: Georgios
authors: G
authors: Vassilikogiannakis