13145-58-9Relevant academic research and scientific papers
Stereoselective reductive coupling of carbonyl compounds by a Sm/Et2AlI system
Nishiyama, Yutaka,Shinomiya, Eiji,Kimura, Shouji,Itoh, Kazuyoshi,Sonoda, Noboru
, p. 3705 - 3708 (1998)
A new method for generation of the samarium (II) species by the reaction of samarium metal with diethylaluminium iodide (Et2AlI) under mild conditions has been developed. Divalent samarium species generated in situ from a Sm/Et2AlI system caused the reductive coupling of aromatic ketones with moderate stereoselectivity to afford corresponding dl-vic-diols in moderate yields.
A novel, solventless reductive coupling of carbonyl compounds by alkali metals, catalysed by bromobenzene
Zhao, Hui,Li, De-Jin,Deng, Lan,Liu, Lei,Guo, Qing-Xiang
, p. 506 - 507 (2003)
Catalysed by bromobenzene, alkali metals including Li, Na, and K can mediate the reductive coupling of carbonyl compounds under mild, solventless conditions to furnish the corresponding pinacol products.
Luminescent tungsten(vi) complexes as photocatalysts for light-driven C-C and C-B bond formation reactions
Chan, Kaai-Tung,Che, Chi-Ming,Du, Lili,Liu, Yungen,Phillips, David Lee,To, Wai-Pong,Tong, Glenna So Ming,Wu, Liang-Liang,Yu, Daohong
, p. 6370 - 6382 (2020/07/15)
The realization of photocatalysis for practical synthetic application hinges on the development of inexpensive photocatalysts which can be prepared on a large scale. Herein an air-stable, visible-light-absorbing photoluminescent tungsten(vi) complex which can be conveniently prepared at the gram-scale is described. This complex could catalyse photochemical organic transformation reactions including borylation of aryl halides, such as aryl chloride, reductive coupling of benzyl bromides for C-C bond formation, reductive coupling of phenacyl bromides, and decarboxylative coupling of redox-active esters of alkyl carboxylic acid with high product yields and broad functional group tolerance.
Lewis Acid Assisted Electrophilic Fluorine-Catalyzed Pinacol Rearrangement of Hydrobenzoin Substrates: One-Pot Synthesis of (±)-Latifine and (±)-Cherylline
Shi, Hui,Du, Chuan,Zhang, Xinhang,Xie, Fukai,Wang, Xiaoyu,Cui, Shanshan,Peng, Xiaoshi,Cheng, Maosheng,Lin, Bin,Liu, Yongxiang
, p. 1312 - 1319 (2018/02/09)
A microwave-irradiated solvent-free pinacol rearrangement of hydrobenzoin substrates catalyzed by a combination of N-fluorobenzenesulfonimide and FeCl3·6H2O was developed. Its selectivity was first investigated by density functional theory (DFT) calculations. Then the functional group tolerance was examined by synthesizing a series of substrates designed based on the insight provided by the DFT calculations. The application of the methodology was demonstrated by the efficient one-pot synthesis of (±)-latifine and (±)-cherylline, both are 4-aryltetrahydroisoquinoline alkaloids isolated from Amaryllidacecae plants.
Air-Stable Blue Phosphorescent Tetradentate Platinum(II) Complexes as Strong Photo-Reductant
Li, Kai,Wan, Qingyun,Yang, Chen,Chang, Xiao-Yong,Low, Kam-Hung,Che, Chi-Ming
supporting information, p. 14129 - 14133 (2018/10/15)
Strong photo-reductants have applications in photo-redox organic synthesis involving reductive activation of C?X(halide) and C=O bonds. We report herein air-stable PtII complexes supported by tetradentate bis(phenolate-NHC) ligands having peripheral electron-donating N-carbazolyl groups. Photo-physical, electrochemical, and computational studies reveal that the presence of N-carbazolyl groups enhances the light absorption and redox reversibility because of its involvement into the frontier MOs in both ground and excited states, making the complexes robust strong photo-reductant with E([Pt]+/*) over ?2.6 V vs. Cp2Fe+/0. The one-electron reduced [Pt]? species are stronger reductants with EPC([Pt]0/?) up to ?3.1 V vs. Cp2Fe+/0. By virtue of the strong reducing nature of these species generated upon light excitation, they can be used in light-driven reductive coupling of carbonyl compounds and reductive debromination of a wide range of unactivated aryl bromides.
Homogeneous and heterogeneous photoredoxcatalyzed hydroxymethylation of ketones and keto esters: Catalyst screening, chemoselectivity and dilution effects
Griesbeck, Axel G.,Reckenthaeler, Melissa
supporting information, p. 1143 - 1150 (2014/06/09)
The homogeneous titanium- and dye-catalyzed as well as the heterogeneous semiconductor particle-catalyzed photohydroxymethylation of ketones by methanol were investigated in order to evaluate the most active photocatalyst system. Dialkoxytitanium dichlorides are the most efficient species for chemoselective hydroxymethylation of acetophenone as well as other aromatic and aliphatic ketones. Pinacol coupling is the dominant process for semiconductor catalysis and ketone reduction dominates the Ti(OiPr)4/methanol or isopropanol systems. Application of dilution effects on the TiO2 catalysis leads to an increase in hydroxymethylation at the expense of the pinacol coupling.
Zn-AlCl3 · 6H2O-mediated reaction in aqueous media: Pinacol coupling reaction
Hazarika, Binod Kumar,Dutta, Dilip Kumar
experimental part, p. 1088 - 1093 (2011/04/25)
(Chemical Equation Presented) Vicinal diols have been prepared in good yield by pinacol coupling reaction of aromatic aldehydes and ketones with commercially available zinc and AlCl3 · 6H2O in water. Copyright Taylor & Francis Group, LLC.
Development of a catalytic electron transfer system mediated by transition metal ate complexes: Applicability and tunability of electron-releasing potential for organic transformations
Uchiyama, Masanobu,Matsumoto, Yotaro,Nakamura, Shinji,Ohwada, Tomohiko,Kobayashi, Nagao,Yamashita, Natsuno,Matsumiya, Atsushi,Sakamoto, Takao
, p. 8755 - 8759 (2007/10/03)
We have developed a catalytic electron transfer (ET) system composed of a transition metal ate complex (Me3M(II)Li; M = Co(II), Mn(II), Fe(II)) and magnesium. This system (catalytic Me3M(II)Li/Mg) turned out to be effective for various ET reactions, such as the desulfonylation of N-phenylsulfonyl amides, and others (the chemoselective cleavage of O-allyl groups, the reduction of nitro groups, the partial reduction of diketones, and the reductive coupling of diphenyliodonium salt). The ET ability of this system can be tuned by changing the ligands of the ate complexes. This tunability was experimentally and electrochemically demonstrated: alkoxy-ligated and dianion-type ET ate complexes showed attenuated and enhanced reducing abilities, respectively. The modification of the ET abilities was evaluated by means of electrochemical measurements and chemical reactions. These results provide a basis for the design of various tailor-made ET ate complexes.
Synthesis of pinacols through electrochemical reduction of carbonyl compounds at platinum cathode in non-aqueous weakly acidic medium
Yadava,Kumar, Sanjeev,Kumar, Anupam,Singh
, p. 595 - 597 (2007/10/03)
The electrochemical reduction of p-methylacetophenone, m-nitrobenzaldehyde p-dimethylaminobenzaldehyde and p-hydroxybenzaldehyde was carried out at controlled potential in weakly acidic medium (phenol, pKa = 9.98) for the purpose of investigating this type of reduction as a possible synthetic procedure for the preparation of 1,2-diol (or pinacol). The products formed during electrolysis at constant cathode potential are reported here.
