Synthesis of an Electron-Rich KITPHOS Monophosphine, Preparation of Derived Metal Complexes and Applications in Catalysis

  1. Lookup NU author(s)
  2. Dr Simon Doherty
  3. Catherine Smyth
  4. Dr Julian Knight
Author(s)Doherty S, Smyth CH, Knight JG, Hashmi SAK
Publication type Article
JournalNature Protocols
ISSN (print)1754-2189
ISSN (electronic)1750-2799
Full text for this publication is not currently held within this repository. Alternative links are provided below where available.
This protocol describes the synthesis of a representative example of the electron-rich biaryl-like KITPHOS class of monophosphine, 11-dicyclohexylphosphino-12-phenyl-9,10-ethenoanthracene (H-KITPHOS). The bicyclic architecture of H-KITPHOS is constructed via [4+2] Diels-Alder cycloaddition between 1-(dicyclohexylphosphinoylethynyl)benzene and anthracene. H-KITPHOS monophosphine is prepared via an operationally straightforward three step procedure and isolated in an overall yield of ~55%. The synthesis of palladium and gold precatalysts of H-KITPHOS are also described; each complex is isolated in excellent yield and in analytically pure form. The palladium complex of H-KITPHOS forms a highly active catalyst for C-C and C-N cross coupling of a range of aryl and heteroaryl chlorides and bromides and the electrophilic Lewis acid gold complex efficiently catalyzes a host of cycloisomerizations. The total time required for the synthesis of H-KITPHOS is 95 h; preparation of corresponding palladium and gold precatalysts requires an additional 7-8 h and if required crystallizations will require a further 48 h.
PublisherNature Publishing Group
Actions    Link to this publication

Altmetrics provided by Altmetric