Superior Effect of a π-Acceptor Ligand (Phosphine−Electron-Deficient Olefin Ligand) in the Negishi Coupling Involving Alkylzinc Reagents

Palladium-catalyzed Negishi cross-coupling involving primary and secondary alkyls, even in the presence of β-H, can be achieved at ambient temperature using chelating ligands containing a phosphine and an electron-deficient olefin. The superior effects of the ligands were shown not only in the desir...

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Bibliographic Details
Published in:Organic letters 2007-10, Vol.9 (22), p.4571-4574
Main Authors: Luo, Xiancai, Zhang, Heng, Duan, Hui, Liu, Qiang, Zhu, Lizheng, Zhang, Tony, Lei, Aiwen
Format: Article
Language:English
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Summary:Palladium-catalyzed Negishi cross-coupling involving primary and secondary alkyls, even in the presence of β-H, can be achieved at ambient temperature using chelating ligands containing a phosphine and an electron-deficient olefin. The superior effects of the ligands were shown not only in the desired cross-coupling product yields but also in the fast reaction at mild conditions. This reaction has been also scaled up to 50 g in 0.005 mol % catalyst (20,000 TONs) at room temperature.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol701995t