Aqueous-Phase, Palladium-Catalyzed Cross-Coupling of Aryl Bromides under Mild Conditions, Using Water-Soluble, Sterically Demanding Alkylphosphines

2004 ◽  
Vol 69 (23) ◽  
pp. 7919-7927 ◽  
Author(s):  
Rebecca B. DeVasher ◽  
Lucas R. Moore ◽  
Kevin H. Shaughnessy
Keyword(s):  
Aqueous Phase ◽  
Cross Coupling ◽  
Water Soluble ◽  
Mild Conditions ◽  
Aryl Bromides ◽  
Sterically Demanding ◽  
Palladium Catalyzed

Monodentate Trialkylphosphines: Privileged Ligands in Metal-catalyzed Crosscoupling Reactions

2020 ◽  
Vol 24 (3) ◽  
pp. 231-264 ◽  
Author(s):  
Kevin H. Shaughnessy
Keyword(s):  
Transition Metal ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Aryl Bromides ◽  
Wide Range ◽  
Sterically Demanding ◽  
Transition Metal Catalyzed ◽  
Catalyzed Reactions ◽  
Metal Catalyzed

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.

Solvent-free palladium-catalyzed C–O cross-coupling of aryl bromides with phenols

2021 ◽  
Vol 31 (3) ◽  
pp. 409-411
Author(s):  
Sergey A. Rzhevskiy ◽  
Maxim A. Topchiy ◽  
Vasilii N. Bogachev ◽  
Lidiya I. Minaeva ◽  
Ilia R. Cherkashchenko ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Solvent Free ◽  
Aryl Bromides ◽  
Palladium Catalyzed

Scope of the Desulfinylative Palladium-Catalyzed Cross-Coupling of Aryl Sulfinates with Aryl Bromides

Synthesis ◽  
2013 ◽  
Vol 45 (05) ◽  
pp. 694-702 ◽  
Author(s):  
Pat Forgione ◽  
Dirk Ortgies ◽  
Alexandre Barthelme ◽  
Sara Aly ◽  
Brigitte Desharnais ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Aryl Bromides ◽  
Palladium Catalyzed

Synthesis of Trifluorostyrene Derivatives by Palladium-Catalyzed Cross-Coupling of Lithium Trimethoxy(trifluorovinyl)borate with Aryl Bromides

2011 ◽  
Vol 18 (2) ◽  
pp. 437-441 ◽  
Author(s):  
Sasa Duric ◽  
Bernd M. Schmidt ◽  
Nina M. Ninnemann ◽  
Dieter Lentz ◽  
C. Christoph Tzschucke
Keyword(s):  
Cross Coupling ◽  
Aryl Bromides ◽  
Palladium Catalyzed

Efficient symmetrical bidentate dioxime ligand-accelerated homogeneous palladium-catalyzed Suzuki–Miyaura coupling reactions of aryl chlorides

2017 ◽  
Vol 41 (1) ◽  
pp. 372-376 ◽  
Author(s):  
Jinyi Song ◽  
Hongyan Zhao ◽  
Yang Liu ◽  
Huatao Han ◽  
Zhuofei Li ◽  
...  
Keyword(s):  
High Activity ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Bidentate Ligands ◽  
Aryl Chlorides ◽  
Arylboronic Acids ◽  
Mild Conditions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

A series of N,O-bidentate ligands were synthesized and studied as high activity ligands for palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of aryl chlorides with arylboronic acids under mild conditions.

scholarly journals Mechanistic Studies of the Palladium-Catalyzed Desulfinative Cross-Coupling of Aryl Bromides and (Hetero)Aryl Sulfinate Salts

2020 ◽  
Vol 142 (7) ◽  
pp. 3564-3576 ◽  
Author(s):  
Antoine de Gombert ◽  
Alasdair I. McKay ◽  
Christopher J. Davis ◽  
Katherine M. Wheelhouse ◽  
Michael C. Willis
Keyword(s):  
Cross Coupling ◽  
Mechanistic Studies ◽  
Aryl Bromides ◽  
Palladium Catalyzed

Facile Buchwald–Hartwig coupling of sterically encumbered substrates effected by PNP ligands

2019 ◽  
Vol 48 (8) ◽  
pp. 2730-2734 ◽  
Author(s):  
Neha Kathewad ◽  
Anagha M. C. ◽  
Nasrina Parvin ◽  
Sneha Parambath ◽  
Pattiyil Parameswaran ◽  
...  
Keyword(s):  
Good Yield ◽  
Cross Coupling ◽  
Sterically Demanding ◽  
Palladium Catalyzed

We employed Ph2PN(Ar)PPh2 ligands for the palladium catalyzed C–N cross coupling of a variety of sterically demanding substrates and isolated very good yield of coupling products.

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