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

Research output: Contribution to journalArticle

22 Citations (Scopus)

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.

LanguageEnglish
Pages4590-4594
Number of pages5
JournalTetrahedron Letters
Volume52
Issue number36
DOIs
Publication statusPublished - 7 Sep 2011

Fingerprint

Thymidine Monophosphate
Alkali Metals
Regioselectivity
Cross Reactions
Lithium
Metals
Molecules
Substrates

Keywords

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

Cite this

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

In: Tetrahedron Letters, Vol. 52, No. 36, 07.09.2011, p. 4590-4594.

Research output: Contribution to journalArticle

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AU - Hevia, Eva

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