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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![[BOND]](http://onlinelibrarystatic.wiley.com/undisplayable_characters/00f8ff.gif)
N and CC Bond Formation
Article first published online: 24 JUL 2008
DOI: 10.1002/adsc.200800307
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Doherty, S., Knight, Julian G., Smyth, Catherine H. and Jorgenson, Graeme A. (2008), Electron-Rich, Bicyclic Biaryl-Like KITPHOS Monophosphines via [4+2] Cycloaddition between 1-Alkynylphosphine Oxides and Anthracene: Highly Efficient Ligands for Palladium-Catalysed CN and CC Bond Formation. Adv. Synth. Catal., 350: 1801–1806. doi: 10.1002/adsc.200800307
Publication History
- Issue published online: 31 JUL 2008
- Article first published online: 24 JUL 2008
- Manuscript Received: 17 MAY 2008
Funded by
- EPSRC
Keywords:
- aminations;
- aryl chlorides;
- biaryl-like compounds;
- electron-rich species;
- phosphines;
- Suzuki–Miyaura coupling
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.