Regioselective ortho lithiation of 3-aryl and 3-styryl furans |
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Authors: | Tofi Maria Georgiou Thomas Montagnon Tamsyn Vassilikogiannakis Georgios |
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Affiliation: | Department of Chemistry, University of Crete, Greece. |
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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. |
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