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.

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.

Chiral Mn(III) Salen Complex Immobilized on CuFe2O4@SiO2-NH2 NPs: A Cheap and Efficient Catalyst for N-arylation of Aryl Halides and Phenylboronic Acid Under Mild Conditions

2020 ◽  
Vol 17 (11) ◽  
pp. 857-863
Author(s):  
Mohammad Ali Nasseri ◽  
Seyyedeh Ameneh Alavi ◽  
Milad Kazemnejadi ◽  
Ali Allahresani
Keyword(s):  
Phenylboronic Acid ◽  
Significant Loss ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Efficient Catalyst ◽  
Aryl Chlorides ◽  
Mild Conditions ◽  
Cross Coupling Reactions ◽  
Salen Complex ◽  
Ft Ir

A convenient and efficient chiral CuFe2O4@SiO2-Mn(III) Ch.salen nanocatalyst has been developed for the C-N cross-coupling reactions of aryl halides/ phenylboronic acid with N-heterocyclic compounds in water and/or DMSO under mild conditions. The catalyst could be applied for the N-arylation of a variety of nitrogen-containing heterocycles with aryl chlorides, bromides, iodides and phenylboronic acid under mild conditions. Moderate to good yields were achieved for all substrates. The structure of catalyst was characterized using various techniques including FT-IR, FE-SEM, EDX, XRD, TEM and TGA. The catalyst can be simply recovered and reused for several times without significant loss of activity.

A Highly Efficient and Recyclable Pd(Pph3)4/Peg-400 System for Stille Cross-Coupling Reactions of Organostannanes with Aryl Bromides

2017 ◽  
Vol 41 (9) ◽  
pp. 547-550
Author(s):  
Xue Huang ◽  
Fang Yao ◽  
Ting Wei ◽  
Mingzhong Cai
Keyword(s):  
Petroleum Ether ◽  
Cross Coupling ◽  
Significant Loss ◽  
Organotin Compounds ◽  
Coupling Reactions ◽  
Efficient Catalyst ◽  
Peg 400 ◽  
Highly Efficient ◽  
Cross Coupling Reactions ◽  
Aryl Bromides

Pd(PPh3)4 in PEG-400 is shown to be a highly efficient catalyst for the Stille cross-coupling reactions of various organotin compounds with aryl bromides. The reaction could be conducted at 80 °C using NaOAc as base, yielding a variety of biaryls, alkynes and alkenes in good to excellent yields. The isolation of the products was readily performed by extraction with petroleum ether and the Pd(PPh3)4/PEG-400 system could be easily recycled and reused five times without any significant loss of activity.

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

ChemInform Abstract: Facile-Prepared Sulfonated Water-Soluble PEPPSI-Pd-NHC Catalysts for Aerobic Aqueous Suzuki-Miyaura Cross-Coupling Reactions.

ChemInform ◽  
2015 ◽  
Vol 46 (17) ◽  
pp. no-no
Author(s):  
Rui Zhong ◽  
Alexander Poethig ◽  
Yinkai Feng ◽  
Korbinian Riener ◽  
Wolfgang A. Herrmann ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Water Soluble ◽  
Coupling Reactions ◽  
Cross Coupling Reactions
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