Ionic liquids are not innocent in Pd catalysis. C–H arylation of thiazolium and imidazolium ionic liquids with aryl halides

2017 ◽  
Vol 4 (9) ◽  
pp. 1863-1866 ◽  
Author(s):  
Takahide Fukuyama ◽  
Md. Taifur Rahman ◽  
Hiroshi Mashima ◽  
Hideo Takahashi ◽  
Ilhyong Ryu
Keyword(s):  
Ionic Liquids ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Imidazolium Ionic Liquids ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

The ionic liquids bearing an aromatic vinylic C–H moiety are not innocent during Pd-catalyzed cross-coupling reactions of aryl halides. Palladium-catalyzed direct C–H arylation of thiazolium and imidazolium ionic liquids took place to give arylated ionic liquids.

Stereodivergent Hydrosilylation, Hydrostannylation, and Hydrogermylation of α-Trifluoromethylated Alkynes and Their Synthetic Applications

Synthesis ◽  
2016 ◽  
Vol 48 (19) ◽  
pp. 3317-3330 ◽  
Author(s):  
Cédric Tresse ◽  
Stéphane Schweizer ◽  
Philippe Bisseret ◽  
Jacques Lalevée ◽  
Gwilherm Evano ◽  
...  
Keyword(s):  
Functional Group ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

Stereoselective hydrometalation reactions of aryl- and alkyl-substituted trifluoromethylated alkynes with triethylsilane, tributylstannane, and triphenylgermane have been investigated. (E)-α-CF3-Vinylsilanes, -stannanes, and -germanes were obtained under palladium-catalyzed conditions whereas the corresponding (Z)-α-CF3-vinylgermanes were obtained under radical conditions. These reactions proceed in good to excellent yields and possess a broad functional group tolerance. Applications of the (Z)- and (E)-α-CF3-vinylgermanes in palladium-catalyzed cross-coupling reactions with aryl halides having diverse electronic requirements were also investigated. The corresponding (Z)- and (E)-α-CF3-styrenes were obtained as single isomers, thus demonstrating the utility of these versatile synthons for the synthesis of stereodefined trifluoromethylated alkenes.

One-pot Synthesis of Dibenzofurans via SNAr and Subsequent Ligand-free Palladium-catalyzed Intramolecular Aryl-aryl Cross-coupling Reactions under Microwave Irradiation

2011 ◽  
Vol 66 (8) ◽  
pp. 833-836
Author(s):  
Zhiping Che ◽  
Hui Xu
Keyword(s):  
Microwave Irradiation ◽  
Cross Coupling ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
One Pot ◽  
One Pot Synthesis ◽  
Cross Coupling Reactions ◽  
Ligand Free ◽  
Palladium Catalyzed ◽  
Snar Reaction

An efficient one-pot synthesis of dibenzofurans, via SNAr reaction of aryl halides and ortho-bromophenols in the presence of anhydrous K2CO3 and subsequent ligand-free palladium-catalyzed intramolecular aryl-aryl cross-coupling cyclization under microwave irradiation, is described.

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