Ambident reactivity of P CH N heterocycles: Lithiation and substitution sites

Joachim Heinicke, Bhaskar R. Aluri, Basit Niaz, Sebastian Burck, Dietrich Gudat, Mark Niemeyer, Oldamur Holloczki, Laszlo Nyulaszi, Peter G. Jones

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Benzofused 1H-1,3-azaphospholes are lithiated at the N-atom by tBuLi but phosphinylation takes place at either the N- or the P-atom. Smaller chlorophosphines react at nitrogen, bulkier react at phosphorus. Substituents at C2 promote the latter mode. N-Substituted 2H-1,3-benzazaphospholes undergo CH-metalation or addition at the P C bond, depending on the conditions, and allow access to 2-functionally substituted benzazaphospholes or their 2,3-dihydro derivatives, new σ2P,X or σ3P,X hybrid ligands (X=O,P).

Original languageEnglish
Pages (from-to)683-687
Number of pages5
JournalPhosphorus, Sulfur and Silicon and the Related Elements
Volume186
Issue number4
DOIs
Publication statusPublished - May 13 2011

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Keywords

  • Ambident reactivity
  • Hybrid ligands
  • Lithiation
  • Phosphenes
  • Phosphinylation
  • Phosphorus heterocycles

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

Heinicke, J., Aluri, B. R., Niaz, B., Burck, S., Gudat, D., Niemeyer, M., Holloczki, O., Nyulaszi, L., & Jones, P. G. (2011). Ambident reactivity of P CH N heterocycles: Lithiation and substitution sites. Phosphorus, Sulfur and Silicon and the Related Elements, 186(4), 683-687. https://doi.org/10.1080/10426507.2010.514486