Tetrahedron letters

Lithiated benzyllithiums from chlorobenzyl chlorides by a DTBB-catalysed lithiation

C Gómez, FF Huerta, M Yus

Index: Gomez, Cecilia; Huerta, Fernando F.; Yus, Miguel Tetrahedron Letters, 1997 , vol. 38, # 4 p. 687 - 690

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Citation Number: 19

Abstract

The reaction of 2-, 3-or 4-chlorobenzyl chlorides (1a-c) with an excess of lithium and a catalytic amount of DTBB (7 mol%) in the presence of different electrophiles [PriCHO, ButCHO, Et2CO,(CH2) 5CO, PhCOMe, Me3SiCl] in THF at− 50° C leads after hydrolysis with water, to the expected dioles or disilylated compounds 2aa-2cf.