119-56-2Relevant articles and documents
Grignard-type carbonyl phenylation in water and under an air atmosphere [1]
Li, Chao-Jun,Meng, Yue
, p. 9538 - 9539 (2000)
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Novel reduction of carbonyl compounds with Al/NH3/halide under irradiation of ultrasonic wave
Sato,Nagaoka,Goto,Saito
, p. 290 - 292 (1990)
Various carbonyl compounds, such as benzophenones and acetophenones, were reduced by Al/NH3/halide under ultrasonic wave irradiation to give the corresponding monohydric alcohols and/or pinacols in satisfactory yields. The addition of inorganic halides improved the selectivity in the formation of monohydric alcohols and pinacols.
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Kohnstam
, p. 2066,2073 (1960)
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Surface modification of CdS quantum dots with fluorinated thiophenol
Hosokawa, Hiroji,Ogata, Tomoyuki,Wada, Yuji,Murakoshi, Kei,Sakata, Takao,Mori, Hirotaro,Yanagida, Shozo
, p. 4575 - 4580 (1996)
CdS nanocrystallites prepared by capping with pentafluorothiophenol, 2,3,5,6-tetrafluorothiophenol or 4-fluorothiophenol are characterized as quantum dots by TEM, FTIR, NMR, UV-VIS and fluorescence spectroscopy. The crystalline size tends to increase with an increase in the number of fluorine atoms in the capping molecules while maintaining high solubility in organic solvents, with solubility in alcohols depending on the number of fluorine atoms in the capping molecules. Pentafluorophenyl-capped CdS nanocrystallites have the highest solubilities in alcohols, and exhibit quantum dot photocatalysis in methanol, leading to the efficient two-electron transfer photoreduction under visible-light irradiation.
Tuning the reactivity of dirhodium(II) complexes with axial N-heterocyclic carbene ligands: The arylation of aldehydes
Gois, Pedro M. P.,Trindade, Alexandre F.,Veiros, Luis F.,Andre, Vania,Duarte, M. Teresa,Afonso, Carlos A. M.,Caddick, Stephen,Cloke, F. Geoffrey N.
, p. 5750 - 5753 (2007)
(Chemical Equation Presented) Efficient dinuclear catalysts: A complex of {Rh2(OAc)4} with two N-heterocyclic carbenes (NHCs) at the axial positions catalyzes the arylation of aldehydes (see picture; R = alkyl, aryl). DFT calculations reveal subtle stereoelectronic effects resulting from the NHC coordination to the dirhodium(II) complex and suggest that complexes with one axial NHC ligand are the catalytically active species.
Semiconductor Photocatalysis: Size Control of Surface-Capped CdS Nanocrystallites and the Quantum Size Effect in Their Photocatalysis
Yanagida, Shozo,Ogata, Tomoyuki,Shindo, Akihiro,Hosokawa, Hiroji,Mori, Hirotaro,et al.
, p. 752 - 758 (1995)
Size-controlled CdS nanocrystallites were prepared by using thiophenol or hexanethiol as a capping reagent by controlling the ratio of Cd2+ to bis(trimethylsilyl) sulfide (S(TMS)2) as a source of the sulfide ion in reversed micelles.Their solubility and photocatalysis were examined.A series of size-controlled phenyl-capped CdS nanocrystallites catalyze the photoreduction of aromatic ketones in the presence of triethylamine as an electron donor under visible-light irradiation.The photocatalytic activity is affected by the particle size, i.e., the reducing power of the photogenerated electron on CdS nanocrystallites toward the ketones increases with decreasing the particle size.The enhancement of photocatalytic activity observed by reducing the particle size should be ascribed to not only a negative shift of the conduction band edge, but also suppression of the formation of surface defects.
Novel rhodium-1,3-dialkyl-3,4,5,6-tetrahydropyrimidin-2-ylidene complexes as catalysts for arylation of aromatic aldehydes
?zdemir, Ismail,Demir, Serpil,?etinkaya, Bekir,?etinkaya, Engin
, p. 5849 - 5855 (2005)
Six new rhodium-tetrahydropyrimidin-2-ylidene complexes (2a-f) have been prepared and characterized by C, H, N analysis, 1H NMR and 13C NMR. Phenylboronic acid reacts with aldehydes in the presence of a catalytic amount of the new rhodium(I)-carbene complexes, RhCl(COD)(1,3- dialkyl-3,4,5,6-tetrahydropyrimidin-2-ylidene), (2a-f), to give the corresponding secondary aryl alcohols in good yields (72-96%).
[Ir(COD)Cl]2/tris(2,4-di-t-butylphenyl)phosphite-catalyzed addition reactions of arylboronic acids with aldehydes
Liao, Yuan-Xi,Dong, Jie,Hu, Qiao-Sheng
, p. 1548 - 1550 (2018)
[Ir(COD)Cl]2/tris(2,4-di-t-butylphenyl)phosphite-catalyzed addition reactions of arylboronic acids with aldehydes were described. The Ir(I) catalyst, generated from [Ir(COD)Cl]2 and tris(2,4-di-t-butylphenyl)phosphite, was an efficient catalyst system for the addition reactions of a variety of arylboronic acids with aromatic and aliphatic aldehydes. The easy availability of the catalyst and good yields make these reactions potentially useful in organic synthesis.
Formation of Secondary Alcohols from the Reaction of Trimethyl- and Methyldiphenyl-telluronium Salts with Aldehydes by Use of Organolithium Reagents
Shi, Li-Lan,Zhou, Zhang-Lin,Huang, Yao-Zeng
, p. 2847 - 2848 (1990)
The telluronium salts (1) and (2), precursors of the non-stabilized telluronium ylide, on treatment with organolithium reagents, reacted with aldehydes to afford secondary alcohols via tetraorganyl tellurium intermediates.
The remarkable role of water during the chemoselective reduction of ketones mediated by metallic aluminium
Bhar, Sanjay,Guha, Sharmistha
, p. 3775 - 3777 (2004)
Diaryl ketones are reduced selectively to the corresponding benzhydrols in good yield by aluminium powder in the presence of sodium hydroxide in the solvent system MeOH:H2O=2:1 whereas dialkyl ketones, α-tetralone, aryl alkyl ketones and cycloalkanones remain mostly unaffected. Interestingly, diaryl ketones remain totally unchanged by the present reagent combination in the absence of water, that is in anhydrous methanol.
In situ generated rhodium-based catalyst for addition of phenylboronic acid to aldehydes
Yigit, Murat,Oezdemir, Ismail,Cetinkaya, Engin,Cetinkaya, Bekir
, p. 461 - 465 (2005)
New 1,3-dialkylperhydrobenzimidazolinium and 1,3-dialkylimidazolinium salts (2,4) as NHC precursors have been synthesized and characterized. These salts in combination with [RhCl(COD)]2 provided active catalysts for the addition of phenylboronic acid to aldehydes under mild conditions. The in situ prepared three-component system [RhCl(COD)]2/imidazolinium salts (2,4) and KOBut catalyse the addition of phenylboronic acid to sterically hindered aldehydes affording the corresponding arylated secondary alcohols in good yields
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Bachmann
, p. 391,394 (1933)
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Nucleophilic substitution reactions of aminoalkylbenzotriazoles with ytterbium metal umpoled diaryl ketones
Su, Weike,Yang, Bibo,Zhang, Yongmin
, p. 2251 - 2253 (2002)
The reaction of diaryl ketones such as benzophenone with aminoalkylbenzotriazoles in the presence of ytterbium metal at room temperature has been found to give 2-amino alcohols in good yields under mild and neutral conditions.
Evidence for rate limiting C-H bond cleavage in the leuckart reaction
Awachie, Peter I.,Agwada, Vincent C.
, p. 1899 - 1910 (1990)
A rho value of +0.21 is reported for the reaction of mono 4-substi- tuted benzophenones with formamide. This, in conjunction with a kinetic iso- tope effect value of 1.80 obtained for the system, suggests a rate-limiting C-H bond cleavage.
Nickel salt-catalyzed addition reaction of arylboronic acids to aromatic aldehydes
Zhou, Li,Du, Xin,He, Ren,Ci, Zhenhua,Bao, Ming
, p. 406 - 408 (2009)
Arylation reaction of aromatic aldehydes with arylboronic acids proceeded smoothly in the presence of a base and catalytic amount of a nickel salt, Ni(ClO4)2·6H2O, in toluene/IPA = 5:1 or IPA to afford corresponding diarylmethanols in good to excellent yields.
Semiconductor Photocatalysis: Effect of Light Intensity on Nanoscale CdS-Catalyzed Photolysis of Organic Substrates
Shiragami, Tsutomu,Fukami, Shinako,Wada, Yuji,Yanagida, Shozo
, p. 12882 - 12887 (1993)
The relationship between light intensity and product distribution in semiconductor photocatalysis was investigated by using nanoscale CdS microcrystallites (CdS-0) as photocatalysts, triethylamine (TEA) as the electron donor, and either aromatic ketones, electron-deficient alkenes, or 1-benzylnicotinamide (BNA+) as substrates.In the case of the ketones and BNA+, the yield of their respective one-electron reduction products, pinacols and the dimer, (BNA)2, increases with decreasing light intensity.When alkenes are employed in the CdS-0 system, cis-trans photoisomerization always occur regardless of the light intensity.The kinetics for the photocatalysis of the alkanes and the measuement of the inital formation rate of active lattice Cd atoms (Cd0) (which act as catalytic sites for two-electron-transfer reductions) reveal that Cd0 formation is proportional to the square of the relative light intensity, Ir2.The chemoselectivity in the photocatalysis using nanoscale CdS should be affected by the quantity of the Cd0, whose formation strongly depends on the light intensity.
Enhanced catalytic activity of one-dimensional CdS @TiO2 core-shell nanocomposites for selective organic transformations under visible LED irradiation
Eskandari, Parvin,Kazemi, Foad,Ramdar, Moosa,Zand, Zahra
, (2021/07/10)
In this study, we are interested in the photocatalytic activity under visible LED irradiation of one- dimensional (1D) CdS @TiO2 core–shell nanocomposites (CSNs) prepared through a facile and convenient method. For the synthesis of 1D CdS@TiO2 core/shell structure, titania source (Tetrabutyl titanate) was hydrolyzed by water vapor transmission on the surface of CdS nanowires (NWs) which were prepared via solvothermal method. The characterization of 1D CdS@TiO2 core–shell nanocomposites (CdS@TiO2 CSNs) was performed using X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), UV–Vis spectroscopy, and UV–Vis diffuse reflectance spectroscopy (DRS). The as-synthesized sample was utilized for the selective reduction of nitro compounds to benzimidazole and anilide, and also the reduction of benzophenones to alcohol under blue LED irradiation. The 1D CdS@TiO2 CSNs exhibited enhanced photoactivity compared with the pure TiO2, CdS nanowires and commercial TiO2-P25. The excellent reusability of the photocatalyst was examined for six runs. The results demonstrated that the prepared sample has the potential to provide a promising visible light-driven photocatalyst for other organic transformations.
Tunable System for Electrochemical Reduction of Ketones and Phthalimides
Chen, Gong,Qiao, Tianjiao,Wang, Yaxin,Zhang, Jian,Zhao, Jianyou
supporting information, p. 3297 - 3302 (2021/10/14)
Herein, we report an efficient, tunable system for electrochemical reduction of ketones and phthalimides at room temperature without the need for stoichiometric external reductants. By utilizing NaN3 as the electrolyte and graphite felt as both the cathode and the anode, we were able to selectively reduce the carbonyl groups of the substrates to alcohols, pinacols, or methylene groups by judiciously choosing the solvent and an acidic additive. The reaction conditions were compatible with a diverse array of functional groups, and phthalimides could undergo one-pot reductive cyclization to afford products with indolizidine scaffolds. Mechanistic studies showed that the reactions involved electron, proton, and hydrogen atom transfers. Importantly, an N3/HN3 cycle operated as a hydrogen atom shuttle, which was critical for reduction of the carbonyl groups to methylene groups.