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

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.
Citing Articles
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This article has been cited by 18 ACS Journal articles (5 most recent appear below).

Organozinc Chemistry Enabled by Micellar Catalysis. Palladium-Catalyzed Cross-Couplings between Alkyl and Aryl Bromides in Water at Room Temperature
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Christophe Duplais, Arkady Krasovskiy, and Bruce H. LipshutzOrganometallics2011 30 (22), 6090-6097Negishi-like cross-couplings between (functionalized) alkyl and aryl bromides are described. Despite the fact that organozinc reagents are intolerant of water, their formation as well as their use in an aqueous micellar environment is discussed herein. ...

TPGS-750-M: A Second-Generation Amphiphile for Metal-Catalyzed Cross-Couplings in Water at Room Temperature
Bruce H. Lipshutz, Subir Ghorai, Alexander R. Abela, Ralph Moser, Takashi Nishikata, Christophe Duplais, and Arkady Krasovskiy , Ricky D. Gaston and Robert C. GadwoodThe Journal of Organic Chemistry2011 Article ASAPTPGS-750-M: A Second-Generation Amphiphile for Metal-Catalyzed Cross-Couplings in Water at Room Temperature
Bruce H. Lipshutz, Subir Ghorai, Alexander R. Abela, Ralph Moser, Takashi Nishikata, Christophe Duplais, and Arkady Krasovskiy , Ricky D. Gaston and Robert C. GadwoodThe Journal of Organic Chemistry2011 Article ASAPAn environmentally benign surfactant (TPGS-750-M), a diester composed of racemic α-tocopherol, MPEG-750, and succinic acid, has been designed and readily prepared as an effective nanomicelle-forming species for general use in metal-catalyzed cross-...

Nickel-Catalyzed Kumada Cross-Coupling Reactions of Tertiary Alkylmagnesium Halides and Aryl Bromides/Triflates
Amruta Joshi-Pangu , Chao-Yuan Wang , and Mark R. BiscoeJournal of the American Chemical Society 0 (ja),Nickel-Catalyzed Kumada Cross-Coupling Reactions of Tertiary Alkylmagnesium Halides and Aryl Bromides/Triflates
Amruta Joshi-Pangu , Chao-Yuan Wang , and Mark R. BiscoeJournal of the American Chemical Society 0 (ja),We report a Ni-catalyzed process for the cross-coupling of tertiary alkyl nucleophiles and aryl bromides. This process is extremely general for a wide range of electrophiles and generally occurs with a ratio of retention to isomerization >30:1. The same ...

Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners
Ranjan Jana, Tejas P. Pathak, and Matthew S. SigmanChemical Reviews2011 111 (3), 1417-1492Advances in Transition Metal (Pd,Ni,Fe)-Catalyzed Cross-Coupling Reactions Using Alkyl-organometallics as Reaction Partners
Ranjan Jana, Tejas P. Pathak, and Matthew S. SigmanChemical Reviews2011 111 (3), 1417-1492

Bond Formations between Two Nucleophiles: Transition Metal Catalyzed Oxidative Cross-Coupling Reactions
Chao Liu, Hua Zhang, Wei Shi, and Aiwen LeiChemical Reviews2011 111 (3), 1780-1824Bond Formations between Two Nucleophiles: Transition Metal Catalyzed Oxidative Cross-Coupling Reactions
Chao Liu, Hua Zhang, Wei Shi, and Aiwen LeiChemical Reviews2011 111 (3), 1780-1824
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History
- Published In Issue October 25, 2007
- Received August 23, 2007
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