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: Pd-Catalyzed Ligand-Free Suzuki Reaction of β-Substituted Allylic Halides with Arylboronic Acids in Water.

ChemInform ◽  
2014 ◽  
Vol 45 (43) ◽  
pp. no-no
Author(s):  
Chaonan Dong ◽  
Lingjuan Zhang ◽  
Xiao Xue ◽  
Huanrong Li ◽  
Zhiyong Yu ◽  
...  
Keyword(s):  
Suzuki Reaction ◽  
Arylboronic Acids ◽  
Ligand Free ◽  
Allylic Halides

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.

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

Inhibition of Homo-coupling of Arylboronic Acids in Ligand Free Pd(II)-Catalyzed Suzuki Reaction

2007 ◽  
Vol 25 (9) ◽  
pp. 1326-1329 ◽  
Author(s):  
Xiao-Chun Tao ◽  
Yue-Ping Zhang ◽  
Tian-Xiong He ◽  
Dong Shen
Keyword(s):  
Suzuki Reaction ◽  
Arylboronic Acids ◽  
Ligand Free

scholarly journals Autocatalytic photoredox Chan-Lam coupling of free diaryl sulfoximines with arylboronic acids

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Cong Wang ◽  
Hui Zhang ◽  
Lucille A. Wells ◽  
Tian Liu ◽  
Tingting Meng ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Hydrogen Atom Abstraction ◽  
Coupling Reactions ◽  
Ambient Light ◽  
Environmental Friendliness ◽  
Copper Species ◽  
Arylboronic Acids ◽  
Ligand Free ◽  
Byproduct Formation ◽  
Electron Reduction

AbstractN-Arylation of NH-sulfoximines represents an appealing approach to access N-aryl sulfoximines, but has not been successfully applied to NH-diaryl sulfoximines. Herein, a copper-catalyzed photoredox dehydrogenative Chan-Lam coupling of free diaryl sulfoximines and arylboronic acids is described. This neutral and ligand-free coupling is initiated by ambient light-induced copper-catalyzed single-electron reduction of NH-sulfoximines. This electron transfer route circumvents the sacrificial oxidant employed in traditional Chan-Lam coupling reactions, increasing the environmental friendliness of this process. Instead, dihydrogen gas forms as a byproduct of this reaction. Mechanistic investigations also reveal a unique autocatalysis process. The C–N coupling products, N-arylated sulfoximines, serve as ligands along with NH-sulfoximine to bind to the copper species, generating the photocatalyst. DFT calculations reveal that both the NH-sulfoximine substrate and the N-aryl product can ligate the copper accounting for the observed autocatalysis. Two energetically viable stepwise pathways were located wherein the copper facilitates hydrogen atom abstraction from the NH-sulfoximine and the ethanol solvent to produce dihydrogen. The protocol described herein represents an appealing alternative strategy to the classic oxidative Chan-Lam reaction, allowing greater substrate generality as well as the elimination of byproduct formation from oxidants.

ChemInform Abstract: Base Promoted Highly Efficient Copper Fluorapatite Catalyzed Coupling of Phenols with Arylboronic Acids under Mild and Ligand-Free Conditions.

ChemInform ◽  
2013 ◽  
Vol 44 (16) ◽  
pp. no-no
Author(s):  
Shafeek A. R. Mulla ◽  
Suleman M. Inamdar ◽  
Mohsinkhan Y. Pathan ◽  
Santosh S. Chavan
Keyword(s):  
Arylboronic Acids ◽  
Highly Efficient ◽  
Ligand Free

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.

ChemInform Abstract: Arylation of Pyridine N-Oxides via a Ligand-Free Suzuki Reaction in Water.

ChemInform ◽  
2015 ◽  
Vol 46 (22) ◽  
pp. no-no
Author(s):  
Chun Liu ◽  
Shao-Ke Zhang ◽  
Yi-Xia Zhang ◽  
Zi-Lin Jin
Keyword(s):  
Suzuki Reaction ◽  
Ligand Free ◽  
Reaction In Water

scholarly journals Ligand-Free (Z)-Selective Transfer Semihydrogenation of Alkynes Catalyzed by in situ Generated Oxidizable Copper Nanoparticles

2021 ◽  
Author(s):  
Rafał Kusy ◽  
Karol Grela
Keyword(s):  
Suzuki Reaction ◽  
Ammonia Borane ◽  
Water Soluble ◽  
Selective Transfer ◽  
One Pot ◽  
Ammonia Complex ◽  
Ligand Free ◽  
Simple Phase ◽  
Operational Simplicity

Herein, we present (<i>Z</i>)-selective transfer semihydrogenation of alkynes based on in situ generated CuNPs in the presence of hydrogen donors, such as ammonia-borane and a protic solvent. This environmentally-friendly method is characterized by operational simplicity combined with high stereo- and chemoselectivity and functional group compatibility. Auto-oxidation of CuNPs after the semihydrogenation reaction is completed results in the formation of water-soluble ammonia complex, so that the catalyst may be reused several times by simple phase-separation with no need of any special regeneration process. Formed NH<sub>4</sub>B(OR)<sub>4</sub> can be easily transformed back to ammonia-borane or to boric acid. In addition, one-pot tandem sequence involving Suzuki reaction followed by semihydrogenation was presented.<br>

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