Pd(η3-1-PhC3H4)(η5-C5H5), an Unusually Effective Catalyst Precursor for Suzuki–Miyaura Cross-Coupling Reactions Catalyzed by Bis-Phosphine Palladium(0) Compounds

2012 ◽  
Vol 31 (6) ◽  
pp. 2470-2475 ◽  
Author(s):  
Andrew W. Fraser ◽  
Jessica E. Besaw ◽  
Laura E. Hull ◽  
Michael C. Baird
Keyword(s):  
Cross Coupling ◽  
Catalyst Precursor ◽  
Coupling Reactions ◽  
Effective Catalyst ◽  
Cross Coupling Reactions

Pd(η3-1-PhC3H4)(η5-C5H5), an Unusually Effective Catalyst Precursor for Heck–Mizoroki and Sonogashira Cross-Coupling Reactions Catalyzed by Bis-Phosphine Palladium(0) Compounds

2012 ◽  
Vol 32 (1) ◽  
pp. 9-11 ◽  
Author(s):  
Andrew W. Fraser ◽  
Bryan E. Jaksic ◽  
Rhys Batcup ◽  
Christopher D. Sarsons ◽  
Michael Woolman ◽  
...  
Keyword(s):  
Cross Coupling ◽  
Catalyst Precursor ◽  
Coupling Reactions ◽  
Effective Catalyst ◽  
Cross Coupling Reactions

Suzuki–Miyaura Cross-Coupling Reactions in Acetic Acid Employing Sydnone-Derived Catalyst Systems

Synlett ◽  
2017 ◽  
Vol 28 (15) ◽  
pp. 1990-1993 ◽  
Author(s):  
Andreas Schmidt ◽  
Ana-Luiza Lücke ◽  
Sascha Wiechmann ◽  
Tyll Freese
Keyword(s):  
Acetic Acid ◽  
Palladium Complex ◽  
Cross Coupling ◽  
Catalyst System ◽  
Boronic Acids ◽  
Coupling Reactions ◽  
Effective Catalyst ◽  
Cross Coupling Reactions ◽  
Catalyst Systems

The catalyst system consisting of lithium N-phenylsydnone-4-carboxylate/Pd(PPh3)4 has proven to be an effective catalyst for the Suzuki–Miyaura reaction of 2,4-dinitrochlorobenzene with boronic acids in acetic acid at pH 5.7, whereas the N-phenylsydnone carbene palladium complex [sydPd(PPh3)2Br] required pH 8.0.

scholarly journals Palladium(II)-catalyzed Suzuki–Miyaura Reactions of Arylboronic Acid with Aryl Halide in the Presence of Aryl-Ferrocenyl-Phosphines

2013 ◽  
Vol 16 (1) ◽  
pp. 79
Author(s):  
A.T. Khabiyev ◽  
B.S. Selenova
Keyword(s):  
Catalytic Activity ◽  
Phenylboronic Acid ◽  
Potassium Phosphate ◽  
Cross Coupling ◽  
Phosphine Ligands ◽  
Catalyst Precursor ◽  
Coupling Reactions ◽  
Weak Base ◽  
Aryl Chlorides ◽  
Cross Coupling Reactions

<p>This study examined investigation of catalytic activity of aryl-ferrocenyl-phosphine (2-methoxyphenyl diferrocenyl phosphine (cat. 1), 2-tert-butyloxyphenyl diferrocenyl phosphine (cat. 2), 2-methoxynaphtyl diferrocenyl phosphine (cat. 3), 1,1’-bis(diphenylphosphino) ferrocene (cat. 4), phenyl diferrocenyl phosphine (cat. 5)) ligands with palladium salts as precursors in Suzuki–Miyaura reaction. Suzuki–Miyaura reaction is one of the important cross-coupling reactions and extremely powerful in forming C–C bonds. Aryl-ferrocenyl-phosphine ligands confer unprecedented activity for these processes, allowing reactions to be performed at low catalyst levels, to prepare extreme This study examined investigation of catalytic activity of aryl-ferrocenyl-phosphine (2-methoxyphenyl diferrocenyl phosphine (cat. 1), 2-tert-butyloxyphenyl diferrocenyl phosphine (cat. 2), 2-methoxynaphtyl diferrocenyl phosphine (cat. 3), 1,1’-bis(diphenylphosphino) ferrocene (cat. 4), phenyl diferrocenyl phosphine (cat. 5)) ligands with palladium salts as precursors in Suzuki–Miyaura reaction. Suzuki–Miyaura reaction is one of the important cross-coupling reactions and extremely powerful in forming C–C bonds. Aryl-ferrocenyl-phosphine ligands confer unprecedented activity for these processes, allowing reactions to be performed at low catalyst levels, to prepare extremely hindered biaryls and to be carried out, in general, also for reactions of aryl chlorides by temperature 100 ºC and pressure 1 atm. Sterically demanding and strongly Lewis-basic ferrocene-based phosphines are water- and oxygen-resistant. The Suzuki–Miyaura reaction is also an important reaction in the ground and fine organic synthesis, in the production of drugs and intermediates. To analyze the conversion of halogen aryl compounds the <sup>1</sup>H NMR spectroscopy was used. The advantage of Suzuki–Miyaura reaction in comparison with other cross-coupling reactions (Kumada-, Heck-, Heck-Carbonylation-, Murahashi-, Sonogashira-, Negishi-, Stille-reaktion, etc.) is in the usage of low toxic, water- and oxygen-insensitive thermostable organoboron compounds. As boronic acid was used phenylboronic acid and as weak base – potassium phosphate. Catalyst, precursor and weak base were dissolved in toluene. All reactions were performed under an atmosphere of nitrogen or argon. The catalytic cycle of Suzuki–Miyaura reaction typically includes three main steps: oxidative addition of the haloaromatic to catalytic active palladium (0) species, transmetalation, and reductive elimination of the product under back formation of catalytically active species. All used catalysts showed good activity with aryl bromides and weak activity with aryl chlorides.</p>

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