Tetrahedron

Regioselectivity in arene-catalyzed reductive lithiation of acetals of chlorobenzaldehydes

U Azzena, G Dettori, G Sforazzini, M Yus, F Foubelo

Index: Azzena, Ugo; Dettori, Giovanna; Sforazzini, Giuseppe; Yus, Miguel; Foubelo, Francisco Tetrahedron, 2006 , vol. 62, # 7 p. 1557 - 1563

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Citation Number: 10

Abstract

The regioselectivity of arene-catalyzed reductive lithiation of acetals of chlorobenzaldehydes strongly depends on the form of lithium metal employed as a reducing agent. According to previous findings, naphthalene catalyzed reductions run in the presence of lithium powder (high Na content) led to competitive metalations of both aromatic carbon–chlorine and benzylic carbon–oxygen bonds. At variance with these results, naphthalene catalyzed ...