Regiospecific silylation of 2, 5-dibromothiophene: a reinvestigation

E Lukevics, P Arsenyan, S Belyakov, J Popelis…

Index: Lukevics, Edmunds; Arsenyan, Pavel; Belyakov, Sergey; Popelis, Juris; Pudova, Olga Tetrahedron Letters, 2001 , vol. 42, # 10 p. 2039 - 2041

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Citation Number: 20

Abstract

Lithiation of 2, 5-dibromothiophene by LDA with ensuing silylation proceeds regiospecifically in accordance with the halogen dance mechanism to yield 3, 5-dibromo-2- trimethylsilylthiophene or 3, 4-dibromo-2, 5-bis (trimethylsilyl) thiophene depending on the ratio of reagents. The outcome of the reaction was confirmed by further chemical transformations of the latter compound to 2, 5-bis (trimethylsilyl) thiophene and 2, 5-bis ( ...