107624-96-4Relevant articles and documents
Aerobic ligand-free Suzuki coupling reaction of aryl chlorides catalyzed by in situ generated palladium nanoparticles at room temperature
Han, Wei,Liu, Chun,Jin, Zilin
, p. 501 - 508 (2008)
An aerobic, ligand-free Suzuki coupling reaction catalyzed by in situ generated palladium nanoparticles in polyethylene glycol with an average molecular weight of 400 Da (PEG-400) at room temperature has been developed. This catalytic system is a very simple and highly active protocol for the Suzuki coupling of aryl chlorides with arylboronic acids, which proceed smoothly in excellent yields in short times using low catalyst loadings. Control experiments demonstrated that the Suzuki reaction catalyzed by the in situ generated palladium nanoparticles can be carried out much quicker than that using the preprepared particles under the same conditions. The formation of palladium nanoparticles in PEG-400 was promoted by arylboronic acids.
Palladium nanoparticles in catalytic carbon nanoreactors: The effect of confinement on Suzuki-Miyaura reactions
Cornelio,Saunders,Solomonsz,Laronze-Cochard,Fontana,Sapi,Khlobystov,Rance
, p. 3918 - 3927 (2015)
We explore the construction and performance of a range of catalytic nanoreactors based on palladium nanoparticles encapsulated in hollow graphitised nanofibres. The optimum catalytic material, with small palladium nanoparticles located almost exclusively at the graphitic step-edges within nanoreactors, exhibits attractive catalytic properties in Suzuki-Miyaura cross-coupling reactions. Confinement of nanoparticles at the step-edges facilitates retention of catalytic centres and recycling of catalytic nanoreactors without any significant loss of activity or selectivity over multiple catalytic cycles. Furthermore, careful comparison of the catalytic properties of palladium nanoparticles either on or in nanoreactors reveals that nanoscale confinement of catalysts fundamentally affects the pathways of the Suzuki-Miyaura reaction, with the yield and selectivity for the cross-coupled product critically dependent on the steric properties of the aryl iodide reactant, whereas no effects of confinement are observed for aryl boronic acid reactants possessing substituents in different positions. These results indicate that the oxidative addition step of the Suzuki-Miyaura reaction occurs at the step-edge of nanofibres, where the mechanisms and kinetics of chemical reactions are known to be sensitive to nanoscale confinement, and thus the extent of confinement in carbon nanoreactors can be discretely controlled by careful selection of the aryl iodide reactant.
Acetanilide palladacycle: An efficient catalyst for room-temperature Suzuki-Miyaura cross-coupling reaction
Dewan, Anindita,Buragohain, Zenith,Mondal, Manoj,Sarmah, Gayatri,Borah, Geetika,Bora, Utpal
, p. 230 - 233 (2014)
The catalytic activity of three acetanilide palladacycles derived from easily accessible and commercially available acetanilide derivatives, viz. N-phenylacetamide (L1), N-(4-chlorophenyl)acetamide (L2) and N-(4-methylphenyl)acetamide (L3) has been examined in Pd-catalyzed Suzuki-Miyaura reaction of arylboronic acid with aryl bromides at room temperature. The complex 1L3 exhibited efficient activity in the Suzuki-Miyaura reaction (up to 99% isolated yield) under mild reaction conditions. Copyright
Polystyrene-resin supported N-heterocyclic carbene-Pd(II) complex based on plant-derived theophylline: A reusable and effective catalyst for the Suzuki-Miyaura cross-coupling reaction of arenediazonium tetrafluoroborate salts with arylboronic acids
Mohammadi, Elmira,Movassagh, Barahman
, p. 62 - 66 (2016)
Polystyrene-supported NHC-Pd(II) complex based on theophylline as a sustainable NHC precursor was employed in the Suzuki-Miyaura cross-coupling reaction of substituted arenediazonium tetrafluoroborate salts with a variety of arylboronic acids to afford functionalized biaryl derivatives in good to excellent yields without using base or additive as promoters. The catalyst was easily recovered by ?ltration and reused for six successive cycles.
Palladium-catalyzed cross-coupling reactions of dry arenediazonium o-benzenedisulfonimides with aryltin compounds
Dughera, Stefano
, p. 1117 - 1122 (2006)
The palladium-catalyzed cross-coupling reaction between various arenediazonium o-benzenedisulfonimides and aryltin derivatives is described. The procedure is general, easy and gives pure biaryls in good yields (25 examples, average yield 79%). o-Benzenedisulfonimide can be recovered (>80%) and reused to prepare again the starting material. Georg Thieme Verlag Stuttgart.
Synthesis of aryl trimethylstannanes from aryl amines: A sandmeyer-type stannylation reaction
Qiu, Di,Meng, He,Jin, Liang,Wang, Shuai,Tang, Shengbo,Wang, Xi,Mo, Fanyang,Zhang, Yan,Wang, Jianbo
, p. 11581 - 11584 (2013)
Sandmeyer-type stannylation: Stille coupling is one of the most powerful coupling reactions for C-C bond formation, whereas there are only limited methods to access aryl stannane compounds. A mild stannylation process based on a Sandmeyer-type transformation using aromatic amines as the starting materials is described. DCE: 1,2-dichloroethane. Copyright
PVC-supported palladium nanoparticles: An efficient catalyst for suzuki cross-coupling reactions at room temperature
Samarasimhareddy, Mamidi,Prabhu, Girish,Vishwanatha, Thimmalapura M.,Sureshbabu, Vommina V.
, p. 1201 - 1206 (2013)
A simple and efficient protocol is described for a Suzuki reaction catalyzed by poly(vinyl chloride)-supported nanoparticles of metallic palladium at room temperature. Aryl iodides, bromides, and chlorides underwent smooth Suzuki reactions in aqueous ethanol, an environmentally friendly solvent, under ligand-free conditions to give good yields of the desired biaryl products. The heterogeneous catalyst could be used up to four times with no detectable metal leaching or loss of catalytic efficiency. Georg Thieme Verlag Stuttgart.New York.
N-heterocyclic carbene coordinated heterogeneous Pd nanoparticles as catalysts for suzuki-miyaura coupling
Min, Hyemin,Miyamura, Hiroyuki,Kobayashi, Shu
, p. 837 - 839 (2016)
Palladium nanoparticle (Pd NP) catalysts immobilized in a polymer with an N-heterocyclic carbene (NHC) moiety (PICBNHC-Pd) have been developed, wherein the NHC moiety plays dual roles as a crosslinker and a ligand to activate the Pd NPs. The presence of both Pd NPs and NHC was confirmed by STEM/EDS and SR-MAS NMR analyses, respectively. This PICB-NHC-Pd catalyst showed excellent activity in the Suzuki-Miyaura coupling reaction without leaching of Pd. Excellent results were obtained in gram-scale synthesis, and catalyst recovery/reuse experiments were completed without loss of catalyst activity.
Fingerprints of singlet and triplet phenyl cations
Slegt, Micha,Overkleeft, Hermen S.,Lodder, Gerrit
, p. 5364 - 5375 (2007)
The photolyses of seven phenyl cation precursors in acetonitrile in the presence of anisole resulted in four distinct product patterns. These patterns are due to the chemoselective and regioselective chemistry of various phenyl cation isomers. This spin-selective chemistry provides a tool with which to fingerprint the singlet/triplet nature of any phenyl cation. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Pyrazole-Mediated C-H Functionalization of Arene and Heteroarenes for Aryl-(Hetero)aryl Cross-Coupling Reactions
Kundu, Abhishek,Dey, Dhananjay,Pal, Subhankar,Adhikari, Debashis
, p. 15665 - 15673 (2021/11/16)
Herein we introduce a transition-metal-free protocol that involves a commercially available, inexpensive pyrazole molecule to conduct C-C cross-coupling reactions at room temperature via a radical pathway. Using this method, an aryldiazonium salt has been coupled to a wide range of arenes and heteroarenes including benzene, mesitylene, thiophene, furan, benzoxazole to result the corresponding biaryl products. The full reaction mechanism is elucidated along with the crystallographic probation of an active initiator species. A potassium-stabilized deprotonated pyrazole steers single-electron transfer to the substrate and behaves as an initiator for the reaction.
