Electron-Rich, Bicyclic Biaryl-Like KITPHOS Monophosphines via [4+2] Cycloaddition between 1-Alkynylphosphine Oxides and Anthracene: Highly Efficient Ligands for Palladium-Catalysed C‒N and C‒C Bond Formation

  1. Lookup NU author(s)
  2. Dr Simon Doherty
  3. Dr Julian Knight
  4. Catherine Smyth
  5. Emeritus Professor William Clegg
Author(s)Doherty S, Knight JG, Smyth CH, Jorgenson GA
Publication type Article
JournalAdvanced Synthesis & Catalysis
Year2008
Volume350
Issue11-12
Pages1801-1806
ISSN (print)1615-4150
ISSN (electronic)1615-4169
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Electron-rich, bicyclic biaryl-like KITPHOS monophosphines have been prepared via Diels-Alder cycloaddition between 1-alkynylphosphine oxides and anthracene in an operationally straightforward and highly modular synthetic protocol that will allow access to an architecturally and electronically diverse family of ligands. Palladium complexes of these ligands are highly efficient catalysts for the Buchwald-Hartwig amination and Suzuki-Miyaura coupling of a wide range of aryl chlorides, which for the vast majority of substrate combinations outperform their o-(dicyclohexylphosphino)biphenyl based counterparts. Keywords: electron rich; biaryl-like; phosphine; aminations; Suzuki-Miyaura coupling; aryl chlorides.
PublisherWiley - VCH Verlag GmbH & Co. KGaA
URLhttp://dx.doi.org/10.1002/adsc.200800307
DOI10.1002/adsc.200800307
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