NiII-(σ-Aryl) Complex Catalyzed Suzuki Reaction of Aryl Tosylates with Arylboronic Acids

2010 ◽  
Vol 2010 (13) ◽  
pp. 2457-2460 ◽  
Author(s):  
Xin-Heng Fan ◽  
Lian-Ming Yang
Keyword(s):  
Suzuki Reaction ◽  
Arylboronic Acids ◽  
Aryl Tosylates

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.

NiCl2(PCy3)2:  A Simple and Efficient Catalyst Precursor for the Suzuki Cross-Coupling of Aryl Tosylates and Arylboronic Acids

2001 ◽  
Vol 3 (19) ◽  
pp. 3049-3051 ◽  
Author(s):  
Danilo Zim ◽  
Vanusa R. Lando ◽  
Jairton Dupont ◽  
Adriano L. Monteiro
Keyword(s):  
Cross Coupling ◽  
Catalyst Precursor ◽  
Efficient Catalyst ◽  
Arylboronic Acids ◽  
Aryl Tosylates

scholarly journals Studies on Pd/NiFe2O4 catalyzed ligand-free Suzuki reaction in aqueous phase: synthesis of biaryls, terphenyls and polyaryls

2011 ◽  
Vol 7 ◽  
pp. 310-319 ◽  
Author(s):  
Sanjay R Borhade ◽  
Suresh Babsaheb Waghmode
Keyword(s):  
Active Catalyst ◽  
Suzuki Reaction ◽  
Reaction Times ◽  
Coupling Reaction ◽  
Solvent Mixture ◽  
Phase Synthesis ◽  
Suzuki Coupling Reaction ◽  
Arylboronic Acids ◽  
Highly Active ◽  
Ligand Free

Palladium supported on nickel ferrite (Pd/NiF2O4) was found to be a highly active catalyst for the Suzuki coupling reaction between various aryl halides and arylboronic acids. The reaction gave excellent yields (70–98%) under ligand free conditions in a 1:1 DMF/H2O solvent mixture, in short reaction times (10–60 min). The catalyst could be recovered easily by applying an external magnetic field. The polyaryls were similarly synthesized.

Pd-catalyzed ligand-free Suzuki reaction of β-substituted allylic halides with arylboronic acids in water

RSC Advances ◽  
2014 ◽  
Vol 4 (22) ◽  
pp. 11152-11158 ◽  
Author(s):  
Chaonan Dong ◽  
Lingjuan Zhang ◽  
Xiao Xue ◽  
Huanrong Li ◽  
Zhiyong Yu ◽  
...  
Keyword(s):  
Suzuki Reaction ◽  
Arylboronic Acids ◽  
Ligand Free ◽  
Allylic Halides

The combination of Pd(TFA)2 and KOH could efficiently catalyze the reaction of β-substituted allylic halides with arylboronic acids in water.

ChemInform Abstract: Inhibition of Homocoupling of Arylboronic Acids in Ligand-Free Pd(II)-Catalyzed Suzuki Reaction.

ChemInform ◽  
2008 ◽  
Vol 39 (5) ◽  
Author(s):  
Xiao-Chun Tao ◽  
Yue-Ping Zhang ◽  
Tian-Xiong He ◽  
Dong Shen
Keyword(s):  
Suzuki Reaction ◽  
Arylboronic Acids ◽  
Ligand Free

scholarly journals A Concise Synthesis of Rhodanthpyrone A and B, Natural 4-(Hydroxyphenyl)-substituted α-Pyrones

2017 ◽  
Vol 12 (1) ◽  
pp. 1934578X1701200
Author(s):  
Young Taek Han
Keyword(s):  
Suzuki Reaction ◽  
Coupling Reaction ◽  
Suzuki Coupling ◽  
Boronic Acids ◽  
Suzuki Coupling Reaction ◽  
Arylboronic Acids ◽  
Model Study ◽  
High Yields ◽  
Phenylboronic Acids

A concise synthesis of rhodanthpyrone A and B was accomplished via a Suzuki coupling reaction. To find the conditions appropriate to install hydroxyphenyl moieties to the α-pyrone skeleton, a model study was conducted using commercially available boronic acids. It was revealed that the hydroxy moiety of the phenylboronic acids should be concealed when reacted with labile 4-tosyl α-pyrone. Consequently, rhodanthpyrone A and B could be synthesized in high yields by Suzuki reaction using TIPS-protected arylboronic acids. This procedure provided a concise and versatile route for the synthesis of rhodanthpyrones and their 4-aryl substituted α-pyrone analogs.

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