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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

Lookup NU author(s): Dr Simon Doherty, Dr Julian Knight, Catherine Smyth, Emeritus Professor Bill Clegg

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Abstract

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.


Publication metadata

Author(s): Doherty S, Knight JG, Smyth CH, Jorgenson GA

Publication type: Article

Journal: Advanced Synthesis & Catalysis

Year: 2008

Volume: 350

Issue: 11-12

Pages: 1801-1806

ISSN (print): 1615-4150

ISSN (electronic): 1615-4169

Publisher: Wiley - VCH Verlag GmbH & Co. KGaA

URL: http://dx.doi.org/10.1002/adsc.200800307

DOI: 10.1002/adsc.200800307


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