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Synthesis of an electron-rich KITPHOS monophosphine, preparation of derived metal complexes and applications in catalysis

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-dihydro-9,10-ethenoanthracene (H-KITPHOS). The bicyclic architecture of H-KITPHOS is constructed via [4+2] Diels-Alder cycloaddit...

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Hauptverfasser: Doherty, Simon (VerfasserIn) , Hashmi, A. Stephen K. (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 2012
In: Nature protocols
Year: 2012, Jahrgang: 7, Heft: 10, Pages: 1870-1883
ISSN:1750-2799
DOI:10.1038/nprot.2012.107
Online-Zugang:Verlag, Volltext: http://dx.doi.org/10.1038/nprot.2012.107
Verlag, Volltext: https://www.nature.com/articles/nprot.2012.107
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Verfasserangaben:Simon Doherty, Catherine H. Smyth, Julian G. Knight & Stephen A.K. Hashmi

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520 |a 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-dihydro-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 is isolated in an overall yield of ∼55%. The synthesis of palladium and gold precatalysts of H-KITPHOS are also described; the yields of analytically pure complexes are high (75-85% and 85-90%, respectively). 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; the preparation of corresponding palladium and gold precatalysts requires an additional 7-8 h, and, if necessary, crystallizations will require a further 48 h. 
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