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Synlett 1990; 1990(12): 755-757
DOI: 10.1055/s-1990-21240
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Preparation and Applications of 2-Iodo-5-lithiothiophene: Synthesis of 8, 11-Thioleukotriene B3

Paulo T. De Sousa Jr.* , Richard J. K. Taylor
  • *School of Chemical Sciences, University of East Anglia, Norwich NR4 7TJ, England
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Publication Date:
08 March 2002 (online)

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The title reagent, prepared by lithiation of 2-iodothiophene using lithium diisopropylamide, reacts with a range of electrophiles; the resulting 5-substituted 2-iodothiophenes undergo efficient Sonogashira alkyne coupling reactions, thereby providing an efficient route to 5-substituted 2-(1-alkynyl)-thiophenes and derivatives. Preliminary details of the scope of this sequence are described as is its application to the synthesis of 8,11-thioleukotriene B3 lithium salt.