scholarly journals Polystyrene-Supported Acyclic Diaminocarbene Palladium Complexes in Sonogashira Cross-Coupling: Stability vs. Catalytic Activity

Catalysts ◽  
2018 ◽  
Vol 8 (4) ◽  
pp. 141 ◽  
Author(s):  
Vladimir Mikhaylov ◽  
Viktor Sorokoumov ◽  
Denis Liakhov ◽  
Alexander Tskhovrebov ◽  
Irina Balova
Keyword(s):  
Catalytic Activity ◽  
High Activity ◽  
Cross Coupling ◽  
Palladium Complexes ◽  
Lower Activity ◽  
Coupling Conditions ◽  
Acyclic Diaminocarbene ◽  
Supported Palladium ◽  
Polymer Supported

Two types of immobilized on the amino-functionalized polystyrene-supported acyclic diaminocarbene palladium complexes (ADC-PdII) are investigated under Sonogashira cross-coupling conditions. Depending on substituents in the diaminocarbene fragment immobilized ADC-PdII, systems are found to have different catalytic activity and stability regarding Pd-leaching. PdII-diaminocarbenes possessing protons at both nitrogen atoms smoothly decompose into Pd0-containing species providing a catalytic “cocktail system” with high activity and ability to reuse within nine runs. Polymer-supported palladium (II) complex bearing NBn–Ccarbene–NH-moiety exhibits greater stability while noticeably lower activity under Sonogashira cross-coupling. Four molecular ADC-PdII complexes are also synthesized and investigated with the aim of confirming proposed base-promoted pathway of ADC-PdII conversion through carbodiimide into an active Pd0 forms.

scholarly journals Amine-Catalysed Suzuki–Miyaura-Type Coupling? the Identification and Isolation of the Palladium Culprits.

2021 ◽  
Author(s):  
Mickaël Avanthay ◽  
Robin Bedford ◽  
Callum Begg ◽  
Dietrich Böse ◽  
Jonathan Clayden ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Cross Coupling ◽  
Boronic Acids ◽  
Palladium Complexes ◽  
Aryl Halides ◽  
Type Coupling ◽  
Paradigm Shifting

A recent report in Nature Catalysis detailed the potentially paradigm-shifting organocatalysis of Suzuki cross-coupling of aryl halides with aryl boronic acids, catalysed by simple amine species. We have conducted a reinvestigation of key claims in this paper across multiple academic and industrial laboratories that shows that the observed catalytic activity cannot be due to the amine, but rather is due to tricyclohexylphosphine palladium complexes that are readily entrained during the purification of the amine<b>.</b>

High activity and stability in the cross-coupling of aryl halides with disulfides over Cu-doped hierarchically porous zeolite ZSM-5

2015 ◽  
Vol 51 (27) ◽  
pp. 5890-5893 ◽  
Author(s):  
Wenqian Fu ◽  
Taotao Liu ◽  
Zhongxue Fang ◽  
Yuli Ma ◽  
Xiang Zheng ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
High Activity ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Macroporous Structure ◽  
Hierarchically Porous ◽  
The Cross

A Cu-doped zeolite ZSM-5 (Cu-ZSM-5-M) with a micro-meso-macroporous structure was directly synthesized, and it exhibits excellent catalytic activity and good recyclability in the cross-coupling of aryl halides with diphenyl disulfides.

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