Tetrahedron letters

Deprotonation of furans using lithium magnesates

F Mongin, A Bucher, JP Bazureau, O Bayh, H Awad…

Index: Mongin, Florence; Bucher, Aurelien; Bazureau, Jean Pierre; Bayh, Omar; Awad, Hacan; Trecourt, Francois Tetrahedron Letters, 2005 , vol. 46, # 46 p. 7989 - 7992

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Citation Number: 54

Abstract

Furan was deprotonated on treatment with 1/3equiv of Bu3MgLi in THF at rt. The lithium arylmagnesate formed was either trapped with electrophiles or involved in a palladium- catalyzed cross-coupling reaction with 2-bromopyridine. The highly coordinated magnesate Bu4MgLi2 (1/3equiv) proved to be a better deprotonating agent than Bu3MgLi; the monitoring of the reaction using NMR spectroscopy showed that the deprotonation of ...