Superior effect of a pi-acceptor ligand (Phosphine-Electron-Deficient olefin ligand) in the Negishi coupling involving alkylzinc reagents

作者:Luo Xiancai; Zhang Heng; Duan Hui; Liu Oiang; Zhu Wheng; Zhang Tony; Lei Aiwen*
来源:Organic Letters, 2007, 9(22): 4571-4574.
DOI:10.1021/o1701995t

摘要

[GRAPHICS]
Palladium-catalyzed Negishi cross-coupling involving primary and secondary alkyls, even in the presence of beta-H, can be achieved at ambient temperature using chelating ligands containing a phospline 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.