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

Xiancai Luo, Heng Zhang, Hui Duan, Qiang Liu, Lizheng Zhu, Tony Zhang, and Aiwen Lei*
College of Chemistry and Molecular Sciences, Wuhan University, PR China, and Eli Lilly and Company, Indianapolis, Indiana 46285
Org. Lett., 2007, 9 (22), pp 4571–4574
DOI: 10.1021/ol701995t
Publication Date (Web): October 6, 2007
Copyright © 2007 American Chemical Society

Abstract

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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.

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History

  • Published In Issue October 25, 2007
  • Received August 23, 2007

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