ChemInform Abstract: Polyfluorinated Phosphine Ligands in the Room Temperature Suzuki Cross-Coupling Reactions.

ChemInform ◽  
2008 ◽  
Vol 39 (8) ◽  
Author(s):  
Shahla Yekta ◽  
Lawrence Cheung ◽  
Andrei K. Yudin
Keyword(s):  
Room Temperature ◽  
Cross Coupling ◽  
Phosphine Ligands ◽  
Coupling Reactions ◽  
Cross Coupling Reactions

Monophosphine Ligands Promote Pd-Catalyzed C–S Cross-Coupling Reactions at Room Temperature with Soluble Bases

2019 ◽  
Author(s):  
Jessica Xu ◽  
Richard Liu ◽  
Charles Yeung ◽  
Stephen L. Buchwald
Keyword(s):  
Transition Metals ◽  
Room Temperature ◽  
Reliable Method ◽  
Cross Coupling ◽  
Phosphine Ligands ◽  
Coupling Reactions ◽  
Late Transition Metals ◽  
Cross Coupling Reactions ◽  
Agricultural Applications ◽  
Late Transition

<div> <p>The Pd-catalyzed cross-coupling of thiols with aromatic electrophiles is a reliable method for the synthesis of aryl thioethers, which are important compounds for pharmaceutical and agricultural applications. Since thiols and thiolates strongly bind late transition metals, previous research has focused on catalysts supported by chelating, bisphosphine ligands, which were considered less likely to be displaced during the course of the reaction. We show that by using monophosphine ligands instead, more effective catalysis can be achieved. Notably, compared to previous methods, this increased reactivity allows for the use of much lower reaction temperature, soluble bases, and base-sensitive substrates. In contrast to conventional wisdom, our mechanistic data suggest that the extent of displacement of phosphine ligands by thiols is, firstly, not correlated with the ligand bulk or thiol nucleophilicity, and secondly, not predictive of the effectiveness of a given ligand in combination with palladium.</p> </div>

Monophosphine Ligands Promote Pd-Catalyzed C–S Cross-Coupling Reactions at Room Temperature with Soluble Bases

2019 ◽  
Author(s):  
Jessica Xu ◽  
Richard Liu ◽  
Charles Yeung ◽  
Stephen L. Buchwald
Keyword(s):  
Transition Metals ◽  
Room Temperature ◽  
Reliable Method ◽  
Cross Coupling ◽  
Phosphine Ligands ◽  
Coupling Reactions ◽  
Late Transition Metals ◽  
Cross Coupling Reactions ◽  
Agricultural Applications ◽  
Late Transition

<div> <p>The Pd-catalyzed cross-coupling of thiols with aromatic electrophiles is a reliable method for the synthesis of aryl thioethers, which are important compounds for pharmaceutical and agricultural applications. Since thiols and thiolates strongly bind late transition metals, previous research has focused on catalysts supported by chelating, bisphosphine ligands, which were considered less likely to be displaced during the course of the reaction. We show that by using monophosphine ligands instead, more effective catalysis can be achieved. Notably, compared to previous methods, this increased reactivity allows for the use of much lower reaction temperature, soluble bases, and base-sensitive substrates. In contrast to conventional wisdom, our mechanistic data suggest that the extent of displacement of phosphine ligands by thiols is, firstly, not correlated with the ligand bulk or thiol nucleophilicity, and secondly, not predictive of the effectiveness of a given ligand in combination with palladium.</p> </div>

Aryl-Diadamantyl Phosphine Ligands in Palladium-Catalyzed Cross-Coupling Reactions: Synthesis, Structural Analysis, and Application

2020 ◽  
Vol 2020 (9) ◽  
pp. 1122-1128
Author(s):  
Ádám Sinai ◽  
Dániel Cs. Simkó ◽  
Fruzsina Szabó ◽  
Attila Paczal ◽  
Tamás Gáti ◽  
...  
Keyword(s):  
Structural Analysis ◽  
Cross Coupling ◽  
Phosphine Ligands ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

scholarly journals Perfluorinated phosphine and hybrid P–O ligands for Pd catalysed C–C bond forming reactions in solution and on Teflon supports

RSC Advances ◽  
2019 ◽  
Vol 9 (50) ◽  
pp. 28936-28945
Author(s):  
Farzana Begum ◽  
Muhammad Ikram ◽  
Brendan Twamley ◽  
Robert J. Baker
Keyword(s):  
Cross Coupling ◽  
Phosphine Ligands ◽  
Coupling Reactions ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Bond Forming Reactions

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.

scholarly journals Synthesis, Structural Analysis and Application of Aryl‐Diadamantyl Phosphine ligands in Palladium Catalyzed Cross‐Coupling Reactions

2020 ◽  
Vol 2020 (34) ◽  
pp. 5634-5634
Author(s):  
Ádám Sinai ◽  
Dániel Cs. Simkó ◽  
Fruzsina Szabó ◽  
Attila Paczal ◽  
Tamás Gáti ◽  
...  
Keyword(s):  
Structural Analysis ◽  
Cross Coupling ◽  
Phosphine Ligands ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

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
Keyword(s):  
Catalytic Activity ◽  
Catalytic Property ◽  
Cross Coupling ◽  
Phosphine Ligands ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Donor And Acceptor ◽  
Detailed Evaluation ◽  
Good Catalytic Activity

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.

Conjugated Polymer Nanoparticles by Suzuki–Miyaura Cross-Coupling Reactions in an Emulsion at Room Temperature

2014 ◽  
Vol 47 (19) ◽  
pp. 6531-6539 ◽  
Author(s):  
Duangratchaneekorn Muenmart ◽  
Andrew B. Foster ◽  
Alan Harvey ◽  
Ming-Tsz Chen ◽  
Oscar Navarro ◽  
...  
Keyword(s):  
Conjugated Polymer ◽  
Room Temperature ◽  
Cross Coupling ◽  
Polymer Nanoparticles ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Conjugated Polymer Nanoparticles
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