82491-65-4Relevant academic research and scientific papers
Bifunctional copper-based photocatalyst for reductive pinacol-type couplings
Caron, Antoine,Morin, émilie,Collins, Shawn K.
, p. 9458 - 9464 (2019/10/11)
A bifunctional copper-based photocatalyst has been prepared that employs a pyrazole-pyridine ligand incorporating a sulfonamide moiety that functions as an intramolecular hydrogen-bond donor for a photochemical PCET process. In typical reductive PCET processes, the photocatalyst and H-bond donor must have an appropriate redox potential and pKa, respectively, to promote the PCET. When working in concert in a bifunctional catalyst such as Cu(pypzs)(BINAP)BF4, the pKa of the H-bond donor can have an acidity that is orders of magnitude less and still efficiently promote the PCET process. A reductive pinacol-type coupling can be performed using a base-metal derived photocatalyst to afford valuable diols (24 examples, 46-99% yield), from readily available aldehydes and ketones.
Highly regioselective and chemoselective titanocene mediated Barbier-type allylation reactions
Morcillo, Sara P.,Martinez-Peragon, Angela,Jakoby, Verena,Mota, Antonio J.,Kube, Christian,Justicia, Jose,Cuerva, Juan M.,Gansaeuer, Andreas
supporting information, p. 2211 - 2213 (2014/02/14)
Titanocene carboxylate 1 is an excellent chemoselective reagent for unprecedented α-regioselective Barbier-type reactions. It constitutes the first titanocene(iii) able to tolerate epoxides and readily reduced carbonyl compounds, such as aromatic and α,β-unsaturated aldehydes. The Royal Society of Chemistry.
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.
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 (2007/10/03)
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.
Efficient method for pinacol coupling of aromatic and aliphatic ketones by using titanium(II) chloride and zinc in the presence of pivalonitrile
Mukaiyama, Teruaki,Kagayama, Akifumi,Shiina, Isamu
, p. 1107 - 1108 (2007/10/03)
The reductive coupling reaction of aromatic and aliphatic ketones including acyclic aliphatic ketones proceeded smoothly to give the corresponding pinacols in good to high yields below room temperature by the combined use of titanium(II) chloride and zinc in the presence of pivalonitrile. Meso-selective formation of the coupling products was observed in the cases with some acyclic aliphatic ketones.
A Convenient Electrochemical Method for Conversion of 4-Haloacetophenone to 1-(4-Halophenyl)ethanol
Ikeda, Yoshikazu
, p. 1719 - 1720 (2007/10/02)
In the presence of a catalytic amount of Sb(III), 4-fluoro-, 4-chloro-, 4-bromo-, and 4-iodoacetophenone were converted into the corresponding 1-(4-halophenyl)ethanols by an electrochemical method (-3,7 mA/cm2, 6F/mol, Pb cathode).Each alcohol yielded 91, 94, 98, and 94percent, respectively.
Kinetics and Mechanism of Polarographic Reduction of Acetophenone and p-Bromoacetophenone in Aqueous Ethanol
Srivastava, M. M.,Singh, Mukhtar,Srivastava, S. N.
, p. 516 - 517 (2007/10/02)
The polarographic behaviour of acetophenone and p-bromoacetophenone in aqueous ethanol (20percent v/v) has been studied at 25+/-O.1 deg C as a function of pH, using Britton-Robinson (BR) buffer.The reduction of the depolarizers in different steps has been found to be diffusion-controlled and irreversible.The kinetic parameters (αna and k0f,h) have been calculated by Koutecky's method.A tentative mechanism has been put forward for the reduction process of each depolarizer.Besides, the effect of substituent (Br) on the kinetics of the electrode reaction of acetophenone has also been investigated.
REDUCTIVE COUPLING OF CARBONYL COMPOUNDS TO PINACOLS BY USING LOW-VALENT CERIUM
Imamoto, Tsuneo,Kusumoto, Tetsuo,Hatanaka, Yasuo,Yokoyama, Masataka
, p. 1353 - 1356 (2007/10/02)
Aldehydes and ketones, on treatment with a low-valent cerium reagent, undergo reductive dimerization to produce the corresponding pinacols in high yield.
