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

Lookup NU author(s): Dr Simon Doherty, Catherine Smyth, Dr Julian Knight

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Abstract

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.


Publication metadata

Author(s): Doherty S, Smyth CH, Knight JG, Hashmi SAK

Publication type: Article

Publication status: Published

Journal: Nature Protocols

Year: 2012

Volume: 7

Pages: 1870-1883

Print publication date: 20/09/2012

ISSN (print): 1754-2189

ISSN (electronic): 1750-2799

Publisher: Nature Publishing Group

URL: http://dx.doi.org/10.1038/nprot.2012.107

DOI: 10.1038/nprot.2012.107


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