In Situ Generation of Phosphoryl Alkylindiums and Their Synthetic Application to Arylalkyl Phosphonates via Palladium-Catalyzed Cross-Coupling Reactions

2014 ◽  
Vol 16 (21) ◽  
pp. 5552-5555 ◽  
Author(s):  
Sanghyuck Kim ◽  
Cheol-Eui Kim ◽  
Boram Seo ◽  
Phil Ho Lee
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
In Situ Generation ◽  
Synthetic Application

Base-Free Synthesis and Synthetic Application of Novel 3-(organochalcogenyl)prop-2-yn-1-yl Esters: Promising Anticancer Agents

Synthesis ◽  
2021 ◽  
Author(s):  
Fabiane Gritzenco ◽  
Jean Carlo Kazmierczak ◽  
Thiago Anjos ◽  
Adriane Sperança ◽  
Maura Luise Bruckchem Peixoto ◽  
...  
Keyword(s):  
Anticancer Agents ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Chalcogen Bond ◽  
Cross Coupling Reactions ◽  
Air Atmosphere ◽  
Carbon Carbon Bonds ◽  
Palladium Catalyzed ◽  
Synthetic Application

This manuscript portrays the CuI-catalyzed Csp-chalcogen bond formation through cross-coupling reactions of propynyl esters and diorganyl dichalcogenides by using DMSO as solvent, at room temperature, under base-free and open-to-air atmosphere. Generally, the reactions have proceeded very smoothly, being tolerant to range of substituents present in both substrates, affording the novel 3-(organochalcogenyl)prop-2-yn-1-yl esters in moderate to good yields. Noteworthy, the 3-(butylselanyl)prop-2-yn-1-yl benzoate proved to be useful as synthetic precursor in palladium-catalyzed Suzuki and Sonogashira type cross-coupling reactions by replacing the carbon-chalcogen bond by new carbon-carbon bonds. Moreover, the 3-(phenylselanyl)prop-2-yn-1-yl benzoate has shown promising in vitro activity against glioblastoma cancer cells.

scholarly journals Regioselective Synthesis of New 2,4-(Het)aryl-3H-pyrido[1′,2′:1,5]pyrazolo[4,3-d]pyrimidines Involving Palladium-Catalyzed Cross-Coupling Reactions

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 2740 ◽  
Author(s):  
Abdelaziz Ejjoummany ◽  
Rabia Belaroussi ◽  
Ahmed El Hakmaoui ◽  
Mohamed Akssira ◽  
Gérald Guillaumet ◽  
...  
Keyword(s):  
Process Optimization ◽  
Cross Coupling ◽  
Regioselective Synthesis ◽  
Coupling Reactions ◽  
Pyrimidine Derivatives ◽  
Release Process ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
High Yields

The design of some novel di-(het)arylated-3H-pyrido[1′,2′:1,5]pyrazolo[4,3-d]pyrimidine derivatives is reported. The series was developed from 1-aminopyridinium iodide, which afforded the key intermediate bearing two thiomethyl and amide functions, each of them useful for palladium catalyzed cross coupling reactions by alkyl sulfur release and C-O activation, respectively. The two regioselective and successive cross-coupling reactions were first carried out in C-4 by in situ C-O activation and next in C-2 by a methylsulfur release. Process optimization furnished conditions leading to products in high yields. The scope and limitations of the methodologies were evaluated and the final compounds characterized.

Palladium-Catalyzed Cross-Coupling of Arenediazonium Salts with Organoindium or Organobismuth Reagents

Synlett ◽  
2018 ◽  
Vol 29 (18) ◽  
pp. 2427-2431
Author(s):  
Bernd Schmidt ◽  
Nastja Riemer ◽  
Christin Coswig ◽  
Mike Shipman
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed ◽  
Arenediazonium Salts

Arylindium and isolated triarylbismuth compounds generated in situ react as nucleophiles with arenediazonium salts in palladium-catalyzed cross-coupling reactions to give substituted biphenyls.

scholarly journals Metformin as a versatile ligand for recyclable palladium-catalyzed cross-coupling reactions in neat water

RSC Advances ◽  
2017 ◽  
Vol 7 (34) ◽  
pp. 21036-21044 ◽  
Author(s):  
S. Fortun ◽  
P. Beauclair ◽  
A. R. Schmitzer
Keyword(s):  
Catalytic Activity ◽  
Cross Coupling ◽  
High Catalytic Activity ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Neat Water ◽  
Palladium Catalyzed

We present the high catalytic activity of an in situ generated palladium(ii)/metformin complex in neat water for the Suzuki–Miyaura and Sonogashira cross-coupling reactions.

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