scholarly journals A Green Synthesis Strategy of Binuclear Catalyst for the C-C Cross-Coupling Reactions in the Aqueous Medium: Hiyama and Suzuki–Miyaura Reactions as Case Studies

2021 ◽  
Vol 9 ◽  
Author(s):  
Pouya Ghamari Kargar ◽  
Ghodsieh Bagherzade

Cellulose, as a green and available phytochemical, was immobilized on the surface of magnetite nanoparticles then doped with imidazole and Co. complex (Fe3O4@CNF ∼ ImSBL ∼ Co.) and used as a water-dispersible, recyclable and efficient nano catalyst for the synthesis of C−C cross-coupling reactions including fluoride-free Hiyama and Suzuki reactions in an aqueous medium as an efficient and vital solvent, due to their high application and importance in various fields of science. Different spectroscopic and microscopic techniques were used for the catalyst characterization such XRD, FESEM, TEM, FT-IR, EDX, DLS, VSM, UV-Vis, and ICP analyses. The presence of imidazole as ionic section tags with hydrophilic character on the Co-complex supported on magnetic nanoparticles provides dispersion of the catalyst particles in water, which leads to both higher catalytic performance and also facile catalyst recovery and reuse six times by successive extraction and final magnetic separation. High catalytic activity was found for the catalyst and high to excellent efficiency was obtained for all Suzuki (80–98% yield; E factor: 1.1–1.9) and Hiyama (87–98% yield; E factor: 0.26–1.1) derivatives in short reaction times under mild reaction conditions in the absence of any hazardous or expensive materials. There is not any noticeable by-product found whether for Suzuki or Hiyama derivatives, which reflects the high selectivity and also the lower the E factor the more favorable is the process in view of green chemistry. The bi-aryls were achieved from the reaction of various aryl iodides/bromides and even chlorides as the highly challenging substrates, which are more available and cheaper, with triethoxyphenylsilane or phenylboronic acid. To prove the performance of the catalyst components (synergistic of SBL ∼ Co. and IL), its different homologs were incorporated individually and studied for a model reaction. Exclusively, this is an introductory statement on the use of Cobalt binuclear symmetric ionic liquid catalysts in Hiyama reactions.

2004 ◽  
Vol 82 (2) ◽  
pp. 206-214 ◽  
Author(s):  
Richard W Friesen ◽  
Laird A Trimble

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 ◽  
2013 ◽  
Vol 44 (18) ◽  
pp. no-no
Author(s):  
Egor V. Verbitskiy ◽  
Gennady L. Rusinov ◽  
Valery N. Charushin ◽  
Oleg N. Chupakhin ◽  
Ekaterina M. Cheprakova ◽  
...  

RSC Advances ◽  
2017 ◽  
Vol 7 (53) ◽  
pp. 33162-33165 ◽  
Author(s):  
Seongsoo Kim ◽  
Hong-Jun Cho ◽  
Namhun Lee ◽  
Yoon-Sik Lee ◽  
Dong-Sik Shin ◽  
...  

A sphere-to-bridge-shaped peptide/Pd(ii) nanostructure was constructed and used as a recyclable Pd nano-catalyst for cross-coupling reactions.


RSC Advances ◽  
2014 ◽  
Vol 4 (53) ◽  
pp. 28148-28155 ◽  
Author(s):  
Joaquim Fernando Mendes da Silva ◽  
Andres Felipe Yepes Perez ◽  
Natália Pinto de Almeida

A simple methodology for Suzuki–Miyaura cross-coupling reactions using microencapsulated palladium and (het)aryl MIDA boronates in water–alcohol under phosphine-free conditions was developed.


Synthesis ◽  
2017 ◽  
Vol 49 (18) ◽  
pp. 4372-4382 ◽  
Author(s):  
Mohammed Waheed ◽  
Naseem Ahmed

2-Hydroxyindan-1-ones have been efficiently synthesized and successfully applied as ligands in Pd-catalyzed Ullmann type, Suzuki–Miyaura, and Mizoroki–Heck cross-coupling reactions with aryl tosylates and aryl halides. The ligands are air- and moisture-stable and have shown high catalytic activity with Pd(OAc)2 in these cross-coupling reactions. The system tolerates a variety of functional groups in the product and can be re-used at least three times with maximum efficiency.


2003 ◽  
Vol 68 (5) ◽  
pp. 837-848 ◽  
Author(s):  
Michal Hocek ◽  
Dana Hocková ◽  
Jan Štambaský

Regioselective Suzuki-Miyaura reaction of 8-bromo-6-iodo-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine with phenylboronic acid gave 8-bromo-6-phenylpurine derivative that was used for cross-coupling reactions (with PhB(OH)2, Me3Al, Et3Al, BnZnCl) or nucleophilic substitutions (with NaOH, NaOMe, NH3, NHMe2 or thiourea). A series of 8-X-substituted 6-phenyl-9-(β-D-ribofuranosyl)purines (X = Ph, Me, Et, Bn, OH, OMe, NH2, NMe2, SH) was prepared in this way directly or after deprotection. None of the title nucleosides exhibited any considerable cytostatic activity.


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