Functionalization of pyridine via direct metallation

…, AVE George, RLP de Jong, L Brandsma

Index: Verbeek, Jacob; George, Albert V. E.; Jong, Robertus L. P. de; Brandsma, Lambert Journal of the Chemical Society, Chemical Communications, 1984 , # 4 p. 257 - 258

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Citation Number: 19

Abstract

The isolation of mixtures of 2-, 3-, and 4-deuteriopyridine, 2-, 3-, and 4-trimethylsilylpyridine, or 2-, 3-, and 4-methylthiopyridine indicates successful metallation of pyridine with a 1 : 1 mixture of BuLi-ButOK in tetrahydrofuran-hexane at -100°C. ... Whereas for most heterocyclic compounds a-metallated derivatives have been obtained by direct metallation with strongly basic organometallic reagents, all efforts to metallate pyridine have so far failed.' Very strong bases such as ...