[reaction: see text] The Suzuki-Miyaura coupling of aryl halides (8 varieties) and aryl- or vinylboronic acids (12 varieties) took place in water in the presence of a palladium complex of an amphiphilic polystyrene-poly(ethylene glycol) copolymer resin-supported N-anchored 2-aza-1,3-bis(diphenylphosphino)propane ligand and potassium carbonate to give uniform and quantitative yields of the corresponding biaryls (96 varieties).
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ol0264298 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Aqueous Asymmetric 1,4-Addition of Arylboronic Acids to Enones Catalyzed by an Amphiphilic Resin-Supported Chiral Diene Rhodium Complex under Batch and Continuous-Flow Conditions.
J Org Chem
July 2018
Institute for Molecular Science (IMS), JST-ACCEL , Okazaki 444-8787 , Japan.
A rhodium-chiral diene complex immobilized on amphiphilic polystyrene-poly(ethylene glycol) (PS-PEG) resin (PS-PEG-diene*-Rh) has been developed. The immobilized rhodium-chiral diene complex (PS-PEG-diene*-Rh) efficiently catalyzed the asymmetric 1,4-addition of various arylboronic acids to cyclic or linear enones in water under batch conditions to give the corresponding β-arylated carbonyl compounds in excellent yields and with excellent enantioselectivity. The catalyst was readily recovered by simple filtration and reused 10 times without loss of its catalytic activity and enantioselectivity.
View Article and Find Full Text PDFHeterogeneous aromatic amination of aryl halides with arylamines in water with PS-PEG resin-supported palladium complexes.
Chem Asian J
August 2010
Frontier Biochemical & Medical Research Laboratories, KANEKA Corporation, Takasago 676-8688, Japan.
Catalytic aromatic amination is achieved in water under heterogeneous conditions by the use of immobilized palladium complexes coordinated with the amphiphilic polystyrene-poly(ethylene glycol) resin-supported di(tert-butyl)phosphine ligand. Aromatic amination of aryl halides with diphenylamine and N,N-double arylation of anilines with bromobenzene were found to proceed in water with broad substrate tolerance to give the triarylamines in high yield with high recyclability of the polymeric catalyst beads. Very little palladium leached from the polymeric catalyst under the water-based reaction conditions to provide a green and clean (metal-uncontaminated) protocol for the preparation of triarylamines, including the optoelectronically active N,N,N',N'-tetraaryl-1,1'-biphenyl-4,4'-diamines (TPDs).
View Article and Find Full Text PDFClean synthesis of triarylamines: Buchwald-Hartwig reaction in water with amphiphilic resin-supported palladium complexes.
Chem Commun (Camb)
February 2010
Institute for Molecular Science, Myodaiji, Okazaki, Aichi 444-8787, Japan.
Catalytic aromatic amination was achieved in water under heterogeneous conditions by the use of palladium complexes anchored to the amphiphilic PS-PEG resin with little palladium leaching to provide a green and clean (metal-uncontaminated) protocol for the preparation of triarylamines, including the optoelectronically active N,N,N',N'-tetraaryl-1,1'-biphenyl-4,4'-diamines (TPDs).
View Article and Find Full Text PDFDevelopment of an amphiphilic resin-dispersion of nanopalladium and nanoplatinum catalysts: design, preparation, and their use in green organic transformations.
Chem Rec
April 2009
Institute for Molecular Science, Higashiyama 5-1, Myodaiji, Okazaki 444-8787, Japan.
An amphiphilic polymer resin-dispersion of nanoparticles of palladium was designed and prepared with a view toward use for catalysis in water. The amphiphilic polystyrene-poly(ethylene glycol) (PS-PEG) resin-dispersion of nanoparticles of palladium exhibited high catalytic performance in the hydrodechlorination of chloroarenes under aqueous conditions. The amphiphilic resin-supported nanopalladium and nanoplatinum particles also catalyzed aerobic oxidation of various alcohols including nonactivated aliphatic and alicyclic alcohols, which is one of the most fundamental and important yet immature processes in organic chemistry, in water under an atmospheric pressure of oxygen gas to form aldehydes, ketones, and carboxylic acids to meet green chemical requirements.
View Article and Find Full Text PDFpi-Allylic C1-substitution in water with nitromethane using amphiphilic resin-supported palladium complexes.
J Org Chem
October 2006
Institute for Molecular Science (IMS) and CREST, Higashiyama 5-1, Myodaiji, Okazaki 444-8787, Japan.
Nitromethane was safely applied as a C1 nucleophile for palladium-catalyzed pi-allylic substitution in water with amphiphilic PS-PEG resin-supported phosphine-palladium complexes. Catalytic asymmetric nitromethylation of cycloalkenyl esters was achieved in water as a single reaction medium under heterogeneous conditions using 5 mol % palladium of a PS-PEG resin-supported palladium-imidazoindolephosphine complex to give optically active (cycloalkenyl)nitromethanes with up to 98% ee.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!