Deprotonation of thiophenes using lithium magnesates

Omar Bayh, Haçan Awad, Florence Mongin*, Christophe Hoarau, François Trécourt, Guy Quéguiner, Francis Marsais, Fernando Blanco, Belén Abarca and Rafael Ballesteros

*Laboratoire de Chimie Organique Fine et Hétérocyclique, UMR 6014, IRCOF, CNRS, Université et INSA de Rouen, Place E. Blondel, BP 08, 76131 Mont-Saint-Aignan Cedex, France, Email: florence.monginuniv-rennes1.fr

O. Bayh, H. Awad, F. Mongin, C. Hoarau, F. Trécourt, G. Quéquiner, F. Marsais, F. Blanco, B. Abarca, R. Ballesteros, Tetrahedron, 2005, 61, 4779-4784.

DOI: 10.1016/j.tet.2005.03.024

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Abstract

Thiophene was regioselectively deprotonated by treatment with Bu₃MgLi in THF at room temperature. The lithium arylmagnesate formed was either trapped with electrophiles or cross-coupled in a ‘one-pot' procedure with aryl halides under palladium catalysis.

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Key Words

Deprotonation, Ate complexes, Magnesium, Thiophenes, Heterobiaryls

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ID: J72-Y2005-2920