Chemoselective Activation of Diethyl Phosphonates: Modular Synthesis of Biologically Relevant Phosphonylated Scaffolds

Pauline Adler, Amandine Pons, Jing Li, Jörg Heider, Bogdan R. Brutiu, Nuno Maulide

Research output: Contribution to journalArticlepeer-review

13 Citations (Scopus)

Abstract

Phosphonates have garnered considerable attention for years owing to both their singular biological properties and their synthetic potential. State-of-the-art methods for the preparation of mixed phosphonates, phosphonamidates, phosphonothioates, and phosphinates rely on harsh and poorly selective reaction conditions. We report herein a mild method for the modular preparation of phosphonylated derivatives, several of which exhibit interesting biological activities, that is based on chemoselective activation with triflic anhydride. This procedure enables flexible and even iterative substitution with a broad range of O, S, N, and C nucleophiles.

Original languageEnglish
Pages (from-to)13330-13334
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number40
DOIs
Publication statusPublished - 2018 Oct 1
Externally publishedYes

Keywords

  • phosphinates
  • phosphonamidates
  • phosphonates
  • phosphonothioates
  • triflic anhydride

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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