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

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  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
Year2012
Volume7
Issue
Pages1870-1883
ISSN (print)1754-2189
ISSN (electronic)1750-2799
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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
URLhttp://dx.doi.org/10.1038/nprot.2012.107
DOI10.1038/nprot.2012.107
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