Ferrocenyl phosphine–oxazaphospholidine oxide ligands for the Suzuki–Miyaura coupling of hindered aryl bromides and chlorides

2009 ◽  
Vol 87 (1) ◽  
pp. 171-175 ◽  
Author(s):  
Daniele Vinci ◽  
Nelson Martins ◽  
Ourida Saidi ◽  
John Bacsa ◽  
Amadeu Brigas ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Boronic Acids ◽  
Coupling Reactions ◽  
Aryl Chlorides ◽  
Cross Coupling Reactions ◽  
Aryl Bromides ◽  
Highly Effective

A series of ferrocenyl oxazaphospholidine phosphines that differ electronically and sterically were investigated as ligands for the Suzuki–Miyaura cross-coupling reactions. One of these compounds, 1, was shown to be highly effective in the coupling reactions of bulky aryl bromides with boronic acids when combined with Pd(OAc)2, while another, 2, was capable of coupling aryl chlorides with boronic acids. However, these ligands were less effective in asymmetric induction.Key words: Suzuki–Miyaura coupling, ferrocenyl phosphines, aryl bromides, aryl chlorides, palladium.

scholarly journals Water-soluble SNS cationic palladium(II) complexes and their Suzuki–Miyaura cross-coupling reactions in aqueous medium

2018 ◽  
Vol 14 ◽  
pp. 1859-1870 ◽  
Author(s):  
Alphonse Fiebor ◽  
Richard Tia ◽  
Banothile C E Makhubela ◽  
Henok H Kinfe
Keyword(s):  
Boronic Acids ◽  
Significant Loss ◽  
Water Soluble ◽  
Pincer Complexes ◽  
Coupling Reactions ◽  
Aryl Chlorides ◽  
Cross Coupling Reactions ◽  
Aryl Bromides ◽  
Cationic Palladium ◽  
Mechanism Of The Reaction

Unlike their SCS analogues, SNS pincer complexes are poorly studied for their use in coupling reactions. Accordingly, a series of water soluble cationic Pd(II) SNS pincer complexes have been successfully synthesised and investigated in detail for their catalytic activity in Suzuki–Miyaura coupling reactions. By using only 0.5 mol % loading of the complexes, the coupling of inactivated aryl bromides and activated aryl chlorides with various boronic acids in water was achieved in excellent yields and the catalysts were found to be reusable for three cycles without a significant loss of activity. The investigation of the mechanism of the reaction revealed that a Pd(II) to Pd(IV) route is the more likely pathway which was further supported by computational studies.

scholarly journals Half-sandwich nickel(II) complexes bearing 1,3-di(cycloalkyl)imidazol-2-ylidene ligands

2015 ◽  
Vol 11 ◽  
pp. 2171-2178 ◽  
Author(s):  
Johnathon Yau ◽  
Kaarel E Hunt ◽  
Laura McDougall ◽  
Alan R Kennedy ◽  
David J Nelson
Keyword(s):  
Cross Coupling ◽  
Nickel Catalysts ◽  
Coupling Reactions ◽  
New Members ◽  
X Ray ◽  
Aryl Chlorides ◽  
X Ray Crystallography ◽  
Cross Coupling Reactions ◽  
Aryl Bromides ◽  
Half Sandwich

Two new nickel catalysts have been prepared using a convenient procedure where nickelocene, the NHC·HBF4 salts, and [Et4N]Cl were heated in THF using microwave irradiation. The resulting [NiCl(Cp)(NHC)] complexes are air- and moisture stable in the solid state, and represent two new members of this valuable and practical class of nickel catalysts. The new species were fully characterised using methods including NMR spectroscopy and X-ray crystallography. When tested in model Suzuki–Miyaura cross-coupling reactions, these complexes were found to be active for the cross-coupling of aryl bromides and aryl chlorides.

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.

The Suzuki-Miyaura Cross-Coupling Reactions of 6-Halopurines with Boronic Acids Leading to 6-Aryl- and 6-Alkenylpurines

Synlett ◽  
1999 ◽  
Vol 1999 (7) ◽  
pp. 1145-1147 ◽  
Author(s):  
Martina Havelková ◽  
Michal Hocek ◽  
Michal Česnek ◽  
Dalimil Dvořák
Keyword(s):  
Cross Coupling ◽  
Boronic Acids ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

scholarly journals Microwave-Enhanced Cross-Coupling Reactions Involving Alkynyltrifluoroborates with Aryl Bromides

Molecules ◽  
2013 ◽  
Vol 18 (2) ◽  
pp. 1755-1761 ◽  
Author(s):  
Vitali Coltuclu ◽  
Eric Dadush ◽  
Abhijit Naravane ◽  
George Kabalka
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Aryl Bromides
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