Alkali-metal mediated zincation of N-heterocyclic substrates using the lithium zincate complex, (THF)Li(TMP)Zn(tBu)(2) and applications in in situ cross coupling reactions

Victoria L. Blair, David C. Blakemore, Duncan Hay, Eva Hevia, David C. Pryde

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Abstract

This study investigates the ability of the mixed-metal reagent [Li(TMP)Zn(tBu)(2)] 1 to promote direct Zn-H exchange reactions (zincations) of a wide range of N-heterocyclic molecules. The generated metallated intermediates from these reactions are intercepted with I-2 and some of them are also employed as precursors in Pd-catalysed Negishi cross-coupling applications. A comparison with recent precedents in metallation chemistry reveals that for some of these heterocycles, 1 allows improved conversions, under milder conditions and in certain cases, even gives unique regioselectivities.

Original languageEnglish
Pages (from-to)4590-4594
Number of pages5
JournalTetrahedron Letters
Volume52
Issue number36
DOIs
Publication statusPublished - 7 Sep 2011

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Keywords

  • metallation
  • zincation
  • N-Heterocycles
  • lithium
  • mixed-metal reagents
  • directed ortho-metalation
  • polysubstituted aromatics
  • functionalized aromatics
  • structual basis
  • magnesium
  • lithiation
  • bases
  • efficient
  • diazines
  • pyrazines

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