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

被引:31
作者
Doherty, Simon [1 ]
Knight, Julian G. [1 ]
Smyth, Catherine H. [1 ]
Jorgenson, Graeme A. [1 ]
机构
[1] Univ Newcastle, Sch Nat Sci, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England
基金
英国工程与自然科学研究理事会;
关键词
aminations; aryl chlorides; biaryl-like compounds; electron-rich species; phosphines; Suzuki-Miyaura coupling;
D O I
10.1002/adsc.200800307
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Electron-rich, bicyclic biaryl-like KIT-PHOS 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.
引用
收藏
页码:1801 / 1806
页数:6
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