Synthesis of an Electron-Rich KITPHOS Monophosphine, Preparation of Derived Metal Complexes and Applications in Catalysis
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- Dr Simon Doherty
- Catherine Smyth
- Dr Julian Knight
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| Author(s) | | Doherty S, Smyth CH, Knight JG, Hashmi SAK |
| Publication type | | Article |
| Journal | | Nature Protocols |
| Year | | 2012 |
| Volume | | 7 |
| Issue | | |
| Pages | | 1870-1883 |
| ISSN (print) | | 1754-2189 |
| ISSN (electronic) | | 1750-2799 |
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| Full text for this publication is not currently held within this repository. Alternative links are provided below where available. |
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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. |
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| Publisher | | Nature Publishing Group |
| URL | | http://dx.doi.org/10.1038/nprot.2012.107 |
| DOI | | 10.1038/nprot.2012.107 |
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