Air-stable Pd(0) catalyst bearing dual phosphine ligands: a detailed evaluation of air stability and catalytic property in cross-coupling reactions

2020 ◽  
Vol 49 (36) ◽  
pp. 12814-12819
Author(s):  
Ryota Sato ◽  
Takaki Kanbara ◽  
Junpei Kuwabara

The Pd(0) complex bearing donor and acceptor phosphine ligands shows long-term air stability and good catalytic activity even in a reaction with a relatively inactive substrate.

2013 ◽  
Vol 16 (1) ◽  
pp. 79
Author(s):  
A.T. Khabiyev ◽  
B.S. Selenova

<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>


2019 ◽  
Vol 10 (1) ◽  
Author(s):  
Tian-Nan Ye ◽  
Yangfan Lu ◽  
Zewen Xiao ◽  
Jiang Li ◽  
Takuya Nakao ◽  
...  

AbstractSuzuki cross-coupling reactions catalyzed by palladium are powerful tools for the synthesis of functional organic compounds. Excellent catalytic activity and stability require negatively charged Pd species and the avoidance of metal leaching or clustering in a heterogeneous system. Here we report a Pd-based electride material, Y3Pd2, in which active Pd atoms are incorporated in a lattice together with Y. As evidenced from detailed characterization and density functional theory (DFT) calculations, Y3Pd2 realizes negatively charged Pd species, a low work function and a high carrier density, which are expected to be beneficial for the efficient Suzuki coupling reaction of activated aryl halides with various coupling partners under mild conditions. The catalytic activity of Y3Pd2 is ten times higher than that of pure Pd and the activation energy is lower by nearly 35%. The Y3Pd2 intermetallic electride catalyst also exhibited extremely good catalytic stability during long-term coupling reactions.


2008 ◽  
Vol 61 (8) ◽  
pp. 610 ◽  
Author(s):  
Guozhi Fan ◽  
Hanjun Zhang ◽  
Siqing Cheng ◽  
Zhandong Ren ◽  
Zhijun Hu ◽  
...  

Palladium chloride anchored on polystyrene modified by 5-amino-1,10-phenanthroline was prepared and used as an efficient recoverable catalyst for Suzuki cross-coupling reactions. The heterogeneous catalysts can be easily separated from the reaction mixture and reused for five cycles without significant Pd leaching and loss of catalytic activity. Rate enhancement in the Suzuki reaction by Lewis acids was also studied.


2014 ◽  
Vol 38 (9) ◽  
pp. 4267-4274 ◽  
Author(s):  
Manoj Trivedi ◽  
Sanjeev kumar Ujjain ◽  
Raj Kishore Sharma ◽  
Gurmeet Singh ◽  
Abhinav Kumar ◽  
...  

A cyano-bridged Cu(ii)–Cu(i) complex was synthesized and transformed into CuO nanoparticles. Their catalytic activity in C–N, C–O, and C–S cross-coupling reactions was explored.


RSC Advances ◽  
2014 ◽  
Vol 4 (69) ◽  
pp. 36437-36443 ◽  
Author(s):  
Zhenhong Guan ◽  
Buyi Li ◽  
Guoliang Hai ◽  
Xinjia Yang ◽  
Tao Li ◽  
...  

Microporous polymers with built-in triphenylphosphine palladium exhibit highly efficient catalytic activity for cross-coupling reactions of benzyl chloride under mild conditions.


2020 ◽  
Vol 2020 (9) ◽  
pp. 1122-1128
Author(s):  
Ádám Sinai ◽  
Dániel Cs. Simkó ◽  
Fruzsina Szabó ◽  
Attila Paczal ◽  
Tamás Gáti ◽  
...  

RSC Advances ◽  
2019 ◽  
Vol 9 (50) ◽  
pp. 28936-28945
Author(s):  
Farzana Begum ◽  
Muhammad Ikram ◽  
Brendan Twamley ◽  
Robert J. Baker

Phosphine ligands containing a perfluorous ponytail can be sorbed onto Teflon tape and used as ligands for C–C cross coupling reactions with little leaching.


Polyhedron ◽  
2016 ◽  
Vol 117 ◽  
pp. 90-96 ◽  
Author(s):  
Vladimír Kuchtanin ◽  
Lucia Kleščíková ◽  
Michal Šoral ◽  
Róbert Fischer ◽  
Zdeňka Růžičková ◽  
...  

Sign in / Sign up

Export Citation Format

Share Document