20765-22-4Relevant academic research and scientific papers
Ring size and nothing else matters: unusual regioselectivity of alkyne hydration by NHC gold(i) complexes
Ageshina, Alexandra A.,Asachenko, Andrey F.,Chesnokov, Gleb A.,Minaeva, Lidiya I.,Nechaev, Mikhail S.,Philippova, Anna N.,Rzhevskiy, Sergey A.,Topchiy, Maxim A.
supporting information, p. 5686 - 5689 (2021/06/16)
We have investigated the role of ring sizes and substituents in NHC ligands in some (NHC)Au(i) complexes in the hydration of internal alkynes. Despite the fact that using (NHC)Au(i) complexes in the hydration of diarylacetylenes leads to Markovnikov-type products, the precise tuning of ligands allows changing the regioselectivity in arylalkylacetylene hydration to the anti-Markovnikov-type.
σ-Bond initiated generation of aryl radicals from aryl diazonium salts
Chan, Bun,McErlean, Christopher S. P.,Nashar, Philippe E.,Tatunashvili, Elene
supporting information, p. 1812 - 1819 (2020/03/17)
σ-Bond nucleophiles and molecular oxygen transform aryl diazonium salts into aryl radicals. Experimental and computational studies show that Hantzsch esters transfer hydride to aryl diazonium species, and that oxygen initiates radical fragmentation of the diazene intermediate to produce aryl radicals. The operational simplicity of this addition-fragmentation process for the generation of aryl radicals, by a polar-radical crossover mechanism, has been illustrated in a variety of bond-forming reactions.
Merging visible-light photoredox and micellar catalysis: Arylation reactions with anilines nitrosated in situ
Bu, Mei-Jie,Lu, Guo-Ping,Jiang, Jianzhong,Cai, Chun
, p. 3728 - 3732 (2018/08/12)
An aqueous photocatalytic system was designed by merging visible-light photoredox catalysis with micellar catalysis. Eosin B, an organic dye, was utilized as the photocatalyst, and Triton X-100 was employed as the surfactant; both are inexpensive and commercially available. This clean and energy-saving catalytic system enables photocatalytic reactions of the diazonium ion generated in situ to proceed smoothly in water without any co-solvents or additives at room temperature.
Salicylic Acid-Catalyzed Arylation of Enol Acetates with Anilines
Felipe-Blanco, Diego,Gonzalez-Gomez, Jose C.
supporting information, p. 2773 - 2778 (2018/07/29)
α-Aryl ketones are both structure moieties commonly found in bioactive compounds and versatile synthetic intermediates for the preparation of drug-like molecules. An operationally simple and scalable protocol has been developed to prepare α-aryl ketones from readily available aromatic amines and enol acetates (or silyl enol ethers). This metal-free methodology features the use of salicylic acid as a convenient catalyst to promote the formation of aryl radicals from in-situ generated aryl diazonium salts, without demanding thermal or photochemical activation. The mild reaction conditions used are compatible with anilines substituted with diverse functionalities. Structural elaboration of some prepared α-aryl ketones was accomplished to illustrate their usefulness as building blocks. (Figure presented.).
Expanding the Hammett Correlations for the Vinylheptafulvene Ring-Closure Reaction
Kilde, Martin Dr?hse,Hansen, Mia Harring,Broman, S?ren Lindb?k,Mikkelsen, Kurt V.,Nielsen, Mogens Br?ndsted
, p. 1052 - 1062 (2017/02/23)
A selection of 2,3-diarylated photochromic dihydroazulenes (DHAs) was prepared by following two different protocols. The first protocol relies on the synthesis of a 3-bromo-substituted dihydroazulene, which is subjected to a Suzuki cross-coupling reaction
Vicinal diaryl azole-based urea derivatives as potential cholesterol lowering agents acting through inhibition of SOAT enzymes
Pal, Palash,Gandhi, Hardik P.,Kanhed, Ashish M.,Patel, Nirali R.,Mankadia, Niraj N.,Baldha, Satish N.,Barmade, Mahesh A.,Murumkar, Prashant R.,Yadav, Mange Ram
, p. 107 - 123 (2017/03/02)
A novel series of vicinal diaryl azole-urea derivatives were synthesized and evaluated for their potential to inhibit SOAT enzyme. Among the reported compounds, compound (12d) emerged as the most potent compound with an IC50value of 2.43?μM. In polaxamer-407 induced lipoprotein lipase inhibition model, compound (12d) reduced triglyceride turnover in?vivo. Compound (12d) also showed dose-dependent prevention of serum total cholesterol and prevention of LDL-C elevation at a dose of 30?mg/kg. Furthermore, compound (12d) showed potential to stop falling levels of serum HDL-C dose-dependently and improved the atherogenic index. Effect of 12d on body weight, plaque formation and development of atherogenic lesions were studied. Toxicological study of compound (12d) indicated that at a dose of 2000?mg/kg, 12d was devoid of any signs of toxicity or mortality.
A family of low molecular-weight, organic catalysts for reductive C-C bond formation
Shaaban, Saad,Jolit, Ana?s,Petkova, Desislava,Maulide, Nuno
, p. 13902 - 13905 (2015/09/15)
Hydrazines form a new family of low molecular-weight reducing agents for diazonium salts. Using only small amounts of hydrazine catalyst, the coupling of diazonium salts to a variety of reactive partners has been achieved, without the requirement for either metal adjuvants or irradiation with visible or ultraviolet light. The generality of the concept proposed herein as well as its advantages in the preparative scale is outlined and discussed.
A new class of "electro-acid/base"-induced reversible methyl ketone colour switches
Zhang, Yu-Mo,Li, Minjie,Li, Wen,Huang, Zhiyuan,Zhu, Shaoyin,Yang, Bing,Wang, Xiao-Chun,Zhang, Sean Xiao-An
, p. 5309 - 5314 (2013/09/23)
Methyl ketone has been designed as a switching unit for electrically addressable molecular colour switches. A newly proposed mechanism of "electro-acid/base" (radical ions)-induced intermolecular proton transfer for the colour switch is proven clearly by cyclic voltammetry (CV), X-ray photoelectron spectroscopy (XPS), infrared spectroscopy (IR) and in situ UV-Vis spectroscopy. A dramatic spectral absorption shift (about 291 nm) is observed during the switching, and blue, yellow and green colours are obtained by adjusting the substituents on the methyl ketone-bridged unit. The in situ "electro-acid/base" is far more convenient than the conventional chemical stimulus of acids or bases for the manipulation of the molecular switching properties. This new switching method and molecular structure manipulation will inspire and accelerate the further development of broad switching materials and applications in ultrathin flexible displays, etc.
On the synthesis and biological properties of isocombretastatins: A case of ketone homologation during Wittig reaction attempts
Stocker, Vivien,Ghinet, Alina,Leman, Marie,Rigo, Benoit,Millet, Regis,Farce, Amaury,Desravines, Deborah,Dubois, Joelle,Waterlot, Christophe,Gautret, Philippe
, p. 3683 - 3696 (2013/04/11)
New isocombretastatins were synthesized by reacting the corresponding phenstatin analogs with CH3PPh3Br in presence of tBuOK. These new derivatives showed significant activities against cellular proliferation and tubulin polymerization. In particular, monomethoxylated derivatives of phenstatin and isoCA-4 exhibit similar activities to those of parent phenstatin. Attempts of the Wittig reaction on 2- (or 4-) methoxy-4′-nitrobenzophenones in the same conditions do not lead to the expected isocombretastatins but to methyleneketones with the exclusion of triphenylphosphine. A mechanism for this new ketone homologation was proposed.
Visible-light-mediated α-arylation of enol acetates using aryl diazonium salts
Hering, Thea,Hari, Durga Prasad,Koenig, Burkhard
, p. 10347 - 10352 (2013/01/15)
Visible light mediates efficiently the α-arylation of enol acetates by aryl diazonium salts under mild conditions using [Ru(bpy)3]Cl 2 as a photoredox catalyst. The broad scope of the reaction toward various diazonium salts and enol acetates was explored. The application of this reaction in the concise synthesis of 2-substituted indoles was demonstrated
