13389-74-7Relevant academic research and scientific papers
Metal-catalyzed release of supported boronic acids for C-C bond formation
Pourbaix, Christelle,Carreaux, Francois,Carboni, Bertrand
, p. 803 - 805 (2001)
matrix presented The viability of solid-supported boronic acids as reagents for Suzuki couplings and nucleophilic additions to aldehydes and enones was successfully demonstrated. This metal-catalyzed cleavage strategy allows the synthesis of a series of functionalized biphenyl products, benzylic alcohols, and β-substituted ketones.
Nickel Catalyzed Intermolecular Carbonyl Addition of Aryl Halide
Ishida, Seima,Suzuki, Hiroyuki,Uchida, Seiichiro,Yamaguchi, Eiji,Itoh, Akichika
supporting information, p. 7483 - 7487 (2019/12/11)
In this study, we develop a nickel-catalyzed carbonyl arylation reaction employing aldehydes with aryl and allyl halides. Various aryl, α,β-unsaturated aldehyde and aliphatic aldehydes can be converted into their corresponding secondary alcohols in moderate-to-high yields. In addition, we extended this approach to develop an asymmetric reductive coupling reaction that combines nickel salts with chiral bisoxazoline ligands to give secondary alcohols with moderate enantioselectivity.
The arylation of aldehydes with arylboronic acids using metal-organic framework Ni(HBTC)BPY as an efficient heterogeneous catalyst
Phan, Nam T.S.,Nguyen, Tung T.,Ta, Anh H.
, p. 95 - 102 (2013/01/14)
A highly crystalline porous Ni(HBTC)BPY was synthesized from the reaction of 1,3,5-benzenetricarboxylic acid, nickel nitrate hexahydrate, and 4,4′-bipyridine by a solvothermal method. Physical characterizations of the solid catalyst were achieved by using several techniques, including X-ray powder diffraction (XRD), scanning electron microscope (SEM), transmission electron microscopy (TEM), thermogravimetric analysis (TGA), Fourier transform infrared (FT-IR), atomic absorption spectrophotometry (AAS), and nitrogen physisorption measurements. The Ni(HBTC)BPY exhibited high catalytic activity in the arylation of aldehydes with arylboronic acids to form diarylmethanols. The catalyst could be separated from the reaction mixture by simple filtration or centrifugation, and could be reused without a significant degradation in catalytic activity. No contribution from homogeneous catalysis of active species leaching into the liquid phase was detected.
A simple procedure for the polymer-supported N-heterocyclic carbene-rhodium complex via click chemistry: A recyclable catalyst for the addition of arylboronic acids to aldehydes
He, Ying,Cai, Chun
supporting information; experimental part, p. 12319 - 12321 (2011/12/15)
A novel polymer-supported carbene-rhodium complex was prepared using a simple procedure via click chemistry. This polymer-supported N-heterocyclic carbene-rhodium complex was characterized and used as a catalyst for the addition of arylboronic acids to aldehydes in good to excellent yields.
Sodium bisulfite: An efficient catalyst for ether formation via dehydration of aromatic/aliphatic alcohol
Wang, Hui,Zhu, Xingfei,Lu, Yangning,Li, Yue,Gao, Xiang
experimental part, p. 1180 - 1184 (2012/04/23)
Straightforward etherification of benzyl alcohols (1) via intermolecular dehydration can be efficiently catalyzed by sodium bisulfite under solvent-free conditions. In the presence of 0.3 mol% or 0.6 mol% amount of sodium bisulfite, symmetric and unsymmetric ethers are prepared from the corresponding alcohols in high yields (up to 95%). Etherification of benzhydryl alcohols is also discussed. Copyright
Novel hexadentate imidazolium salts in the rhodium-catalyzed addition of arylboronic acids to aldehydes
Chen, Junhua,Zhang, Xiaoqin,Feng, Qiang,Luo, Meiming
, p. 470 - 474 (2007/10/03)
Four novel hexadentate imidazolium salts were synthesized from hexakis(bromomethyl)benzene and 1-substituted imidazole. The arylation of aldehydes with arylboronic acids was effected conveniently and in high yields by a catalyst system generated in situ from these hexadentate imidazolium salts, [Rh(COD)Cl]2 and a base.
Polymer-supported N-heterocyclic carbene-rhodium complex catalyst for the addition of arylboronic acids to aldehydes
Yan, Chun,Zeng, Xiaoming,Zhang, Weifeng,Luo, Meiming
, p. 3391 - 3396 (2007/10/03)
A novel polymer-supported N-heterocylic carbene (NHC)-rhodium complex was prepared from chloromethyl polystyrene (CM PS) resin using a simple procedure. This polymer-supported NHC-rhodium complex was used as a catalyst for the addition of arylboronic acids to aldehydes affording arylmethanols in excellent yields.
Direct observation of aldehyde insertion into rhodium-aryl and -alkoxide complexes
Krug, Christopher,Hartwig, John F.
, p. 1674 - 1679 (2007/10/03)
Several organorhodium(I) complexes of the general formula (PPh3)2(CO)RhR (R = p-tolyl, o-tolyl, Me) were isolated and were shown to insert aryl aldehydes into the aryl-rhodium(I) bond. Under nonaqueous conditions, these reactions provided ketones in good yield. The stability of the arylrhodium(I) complexes allowed these reactions to be run also in mixtures of THF and water. In this solvent system, diarylmethanols were generated exclusively. Mechanistic studies support the formation of ketone and diarylmethanol by insertion of aldehyde into the rhodium-aryl bond and subsequent β-hydride elimination or hydrolysis to form diaryl ketone or diarylmethanol products. Kinetic isotope effects and the formation of diarylmethanols in THF/water mixtures are inconsistent with oxidative addition of the acyl carbon-hydrogen bond and reductive elimination to form ketone. Moreover, the intermediate rhodium diarylmethoxide formed from insertion of aldehyde was observed directly during the reaction. Its structure was confirmed by independent synthesis. This complex undergoes β-hydrogen elimination to form a ketone. This alkoxide also reacts with a second aldehyde to form esters by insertion and subsequent β-hydrogen elimination. Thus, reactions of arylrhodium complexes with an excess of aldehyde formed esters by a double insertion and β-hydrogen elimination sequence.
Synthesis, Absolute Configuration and Circular Dichroism of Some Diarylmethane Derivatives
Stanchev, Stephan,Rakovska, Rosiza,Berova, Nikolina,Snatzke, Guenter
, p. 183 - 198 (2007/10/02)
Synthesis and assignment of the absolute configuration of different types of compounds bearing the diarylmethane moiety is presented.The absolute configuration was determined using chemical correlation and CD approaches based on the sign of the O-O vibronic transition within the α-aromatic (1Lb) band of the substituted phenyl chromophore.
