Comparison of the Suzuki Cross-Coupling Reactions of 4,7-Dichloroquinoline and 7-Chloro-4-iodoquinoline with Arylboronic Acids Using Phosphine-Free Palladium Catalysis in Water.

ChemInform ◽  
2004 ◽  
Vol 35 (33) ◽  
Author(s):  
Richard W. Friesen ◽  
Laird A. Trimble
Keyword(s):  
Palladium Catalysis ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Arylboronic Acids ◽  
Cross Coupling Reactions

Comparison of the Suzuki cross-coupling reactions of 4,7-dichloroquinoline and 7-chloro-4-iodoquinoline with arylboronic acids using phosphine-free palladium catalysis in water

2004 ◽  
Vol 82 (2) ◽  
pp. 206-214 ◽  
Author(s):  
Richard W Friesen ◽  
Laird A Trimble
Keyword(s):  
Phenylboronic Acid ◽  
Palladium Catalysis ◽  
Suzuki Reaction ◽  
Tetrabutylammonium Bromide ◽  
Cross Coupling ◽  
Palladium Acetate ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Arylboronic Acids ◽  
Cross Coupling Reactions

4,7-Dichloroquinoline (1a) and 7-chloro-4-iodoquinoline (1b) undergo Suzuki cross-coupling reactions with arylboronic acids catalyzed by phosphine-free palladium acetate in boiling water. Using phenylboronic acid (2), the reaction of 1a provides 7-chloro-4-phenylquinoline (3) (78%) together with diphenylquinoline (4) (12%), while 1b reacts in a much more regioselective fashion and provides 3 in 98% isolated yield. Although 1b undergoes a more regioselective Suzuki reaction than 1a, additional important observations are that the overall reaction of 1b with 2 is three times slower than 1a and that the reaction occurs in the absence of tetrabutylammonium bromide. Using optimized reaction conditions, a variety of aryl and vinylboronic acids undergo regioselective Suzuki cross-coupling with 1b to provide the products 7, 10, and 11 in good to excellent yield.Key words: palladium, cross-coupling, regioselectivity, quinolines, boronic acids.

Efficient symmetrical bidentate dioxime ligand-accelerated homogeneous palladium-catalyzed Suzuki–Miyaura coupling reactions of aryl chlorides

2017 ◽  
Vol 41 (1) ◽  
pp. 372-376 ◽  
Author(s):  
Jinyi Song ◽  
Hongyan Zhao ◽  
Yang Liu ◽  
Huatao Han ◽  
Zhuofei Li ◽  
...  
Keyword(s):  
High Activity ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Bidentate Ligands ◽  
Aryl Chlorides ◽  
Arylboronic Acids ◽  
Mild Conditions ◽  
Cross Coupling Reactions ◽  
Palladium Catalyzed

A series of N,O-bidentate ligands were synthesized and studied as high activity ligands for palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of aryl chlorides with arylboronic acids under mild conditions.

Palladium-catalysed cross-coupling reactions of arylboronic acids with π-deficient heteroaryl chlorides

Tetrahedron ◽  
1992 ◽  
Vol 48 (37) ◽  
pp. 8117-8126 ◽  
Author(s):  
Naji M. Ali ◽  
Alexander McKillop ◽  
Michael B. Mitchell ◽  
Ricardo A. Rebelo ◽  
Philip J. Wallbank
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Arylboronic Acids ◽  
Cross Coupling Reactions
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