Addition of a Cyclophosphine to Nitriles: An Inorganic Click Reaction Featuring Protio, Organo, and Main-Group Catalysis: An Inorganic Click Reaction Featuring Protio, Organo, and Main-Group Catalysis

Saurabh Chitnis, Hazel Sparkes, Vincent Annibale, Natalie Pridmore, Alex Oliver, Ian Manners

Research output: Contribution to journalArticle (Academic Journal)peer-review

21 Citations (Scopus)
347 Downloads (Pure)

Abstract

We report the addition of a cyclotriphosphine to a broad range of nitriles giving access to the first examples of free 1-aza-2,3,4-triphospholenes in a rapid, ambient temperature, one-pot, high-yield protocol. The reaction produces electron-rich heterocycles (four lone pairs) and features homoatomic σ-bond heterolysis, thereby combining the key features of the 1,3-dipolar cycloaddition chemistry of azides and cyclopropanes. We also report the first catalytic addition of P-P bonds to the C≡N triple bond. The coordination chemistry of the new heterocycles is explored.
Original languageEnglish
Pages (from-to)9536
Number of pages9540
JournalAngewandte Chemie - International Edition
Volume56
Early online date7 Jul 2017
DOIs
Publication statusPublished - 27 Jul 2017

Keywords

  • click chemistry
  • Cycloaddition
  • HETEROCYCLES
  • main-group elements
  • Phosphorus

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