Monodentate Trialkylphosphines: Privileged Ligands in Metal-Catalyzed Cross- Coupling Reactions

Author(s): Kevin H. Shaughnessy*.

Journal Name: Current Organic Chemistry

Volume 24 , Issue 3 , 2020

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Phosphines are widely used ligands in transition metal-catalyzed reactions. Arylphosphines, such as triphenylphosphine, were among the first phosphines to show broad utility in catalysis. Beginning in the late 1990s, sterically demanding and electronrich trialkylphosphines began to receive attention as supporting ligands. These ligands were found to be particularly effective at promoting oxidative addition in cross-coupling of aryl halides. With electron-rich, sterically demanding ligands, such as tri-tertbutylphosphine, coupling of aryl bromides could be achieved at room temperature. More importantly, the less reactive, but more broadly available, aryl chlorides became accessible substrates. Tri-tert-butylphosphine has become a privileged ligand that has found application in a wide range of late transition-metal catalyzed coupling reactions. This success has led to the use of numerous monodentate trialkylphosphines in cross-coupling reactions. This review will discuss the general properties and features of monodentate trialkylphosphines and their application in cross-coupling reactions of C–X and C–H bonds.

Keywords: Phosphine, cross-coupling, steric parameter, electronic parameter, palladium, monodentate trialkylphosphines, palladiumphosphine.

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Article Details

Year: 2020
Page: [231 - 264]
Pages: 34
DOI: 10.2174/1385272824666200211114540
Price: $95

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