66693-06-9Relevant academic research and scientific papers
Copper-Catalyzed Cross-Nucleophile Coupling of β-Allenyl Silanes with Tertiary C-H Bonds: A Radical Approach to Branched 1,3-Dienes
Shan, Qi-Chao,Hu, Lu-Min,Qin, Wei,Hu, Xu-Hong
supporting information, p. 6041 - 6045 (2021/08/03)
Described herein is a distinctive approach to branched 1,3-dienes through oxidative coupling of two nucleophilic substrates, β-allenyl silanes, and hydrocarbons appending latent functionality by copper catalysis. Notably, C(sp3)-H dienylation proceeded in a regiospecific manner, even in the presence of competitive C-H bonds that are capable of occurring hydrogen atom transfer process, such as those located at benzylic and other tertiary sites, or adjacent to an oxygen atom. Control experiments support the intermediacy of functionalized alkyl radicals.
Cross coupling of sulfonyl radicals with silver-based carbenes: A simple approach to β-carbonyl arylsulfones
Li, Jingjing,Lian, Pengcheng,Wan, Xiaobing,Wang, Hanghang,Zheng, Yonggao
, p. 2163 - 2169 (2020/03/27)
A coupling reaction between sulfonyl radicals and silver-based carbenes has been well established. This simple radical-carbene coupling (RCC) process provided an efficient approach to a variety of β-carbonyl arylsulfones from sodium arylsulfinates and diazo compounds, and was characterized by wide substrate scope, easy scale-up, simple manipulation, accessible starting materials, and mild reaction conditions.
Method for preparing beta-carbonyl sulfone
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Paragraph 0029; 0030, (2020/03/12)
The invention discloses a method for preparing beta-carbonyl sulfone. The preparation method comprises the following steps: by taking an alpha-carbonyl diazo compound and sodium arylsulfinate as reaction substrates, cheap silver nitrate as an optimal catalyst, 1, 10-phenanthroline as a ligand and potassium persulfate as an oxidant, carrying out coupling reaction in a mixed solvent of acetonitrileand water to obtain the beta-carbonyl sulfone compound. Compared with the prior art, the method has the advantages of wide reaction substrate range, short reaction time, high reaction yield, mild reaction conditions and the like. Non-toxic and harmless reagents are used as reaction raw materials, so that the method is harmless to the environment and meets the requirements of modern green chemicaldevelopment. Post-reaction treatment is simple, and separation and purification are facilitated. In addition, the reaction can realize gram-scale synthesis, and lays a foundation for practical application.
Switching of Sulfonylation Selectivity by Nature of Solvent and Temperature: The Reaction of β-Dicarbonyl Compounds with Sodium Sulfinates under the Action of Iron-Based Oxidants
Mulina, Olga M.,Pirgach, Dmitry A.,Nikishin, Gennady I.,Terent'ev, Alexander O.
, p. 4179 - 4188 (2019/05/08)
Selectivity of sulfonylation of β-keto esters with sodium sulfinates under the action of iron(III) salts as oxidants can be regulated by the type of solvent used and the reaction temperature. α-Sulfonyl β-keto esters are obtained when the process is conducted in THF/H2O solution at 40 °C. The change of the solvent to iPrOH/H2O and refluxing of a reaction mixture provides α-sulfonyl esters – the products of successive sulfonylation-deacylation. When β-diketones are applied as starting materials, only α-sulfonyl ketones are formed. The reaction pathway includes sulfonylation of dicabonyl compounds under the action of Fe(III) to form α-sulfonylated dicarbonyl compounds, which are then attacked by a solvent as the nucleophile, resulting in the products of successive sulfonylation-deacylation. Participation of the solvent in the reaction pathway determines the products structure.
Regioselective Copper-Catalyzed Oxidative Coupling of α-Alkylated Styrenes with Tertiary Alkyl Radicals
Wang, Cong,Liu, Rui-Hua,Tian, Ming-Qing,Hu, Xu-Hong,Loh, Teck-Peng
supporting information, p. 4032 - 4035 (2018/07/15)
A radical-mediated oxidative cross-coupling of readily accessible α-alkylated styrenes with 1,3-dicarbonyl compounds utilizing a combination of Cu(OAc)2 and air as a catalytic system is described. Rather than requiring α-halocarbonyl compounds, this efficient approach enables direct installation of tertiary functionalized alkyl motifs to olefins with simple carbonyl derivatives. The novel protocol is characterized with high allylic selectivities via a competing β-H elimination. Both radical-clock and -trapping experiments provided clear-cut evidence for the intermediacy of an α-keto carbon-centered radical.
Potent inhibitors of LpxC for the treatment of gram-negative infections
Brown, Matthew F.,Reilly, Usa,Abramite, Joseph A.,Arcari, Joel T.,Oliver, Robert,Barham, Rose A.,Che, Ye,Chen, Jinshan Michael,Collantes, Elizabeth M.,Chung, Seung Won,Desbonnet, Charlene,Doty, Jonathan,Doroski, Matthew,Engtrakul, Juntyma J.,Harris, Thomas M.,Huband, Michael,Knafels, John D.,Leach, Karen L.,Liu, Shenping,Marfat, Anthony,Marra, Andrea,McElroy, Eric,Melnick, Michael,Menard, Carol A.,Montgomery, Justin I.,Mullins, Lisa,Noe, Mark. C.,O'Donnell, John,Penzien, Joseph,Plummer, Mark S.,Price, Loren M.,Shanmugasundaram, Veerabahu,Thoma, Christy,Uccello, Daniel P.,Warmus, Joseph S.,Wishka, Donn G.
supporting information; experimental part, p. 914 - 923 (2012/03/27)
In this paper, we present the synthesis and SAR as well as selectivity, pharmacokinetic, and infection model data for representative analogues of a novel series of potent antibacterial LpxC inhibitors represented by hydroxamic acid 1a.
[2 + 1] Cycloaddition Reactions of a 1-Seleno-2-silylethene to 2-Sulfonylacrylates: Stereoselective Synthesis of Sulfone-Substituted Cyclopropanes
Yamazaki, Shoko,Yanase, Yuichiro,Tanigawa, Etsuko,Yamabe, Shinichi,Tamura, Hatsue
, p. 9521 - 9528 (2007/10/03)
Reaction of 1-(phenylseleno)-2-(trimethylsilyl)ethene 1 and methyl or ethyl 2-p-toluene- or benzene-sulfonylacrylates 3 in the presence of SnCl4 at -78°C gave sulfone-substituted cyclopropanes 4 as single stereoisomers. The structure of one of these crystalline cyclopropane products was elucidated by X-ray crystallographic analysis. The relative stereochemistry of the cyclopropane ring carbon (C2) and selenosilylmethyl group was determined as R,R and S,S, which is consistent with previous mechanical considerations and the NOE determination. 2-Sulfinyl acrylate 2 did not undergo this cycloaddition. The difference in reactivity of the sulfoxide 2 and sulfones 3 toward 1 was explained by comparison of LUMO levels of 2-SnCl4 and 3-SnCl4 complexes and activation energies in the synclinal addition of 1 to the complexes.
Chemoselective oxidation of sulfides to sulfones with magnesium monoperoxyphthalate (MMPP) on silica gel support in methylene chloride solvent
Ali, Mohammed Hashmat,Bohnert, Gary J.
, p. 2983 - 2998 (2007/10/03)
A simple, efficient and chemoselective, non-aqueous procedure for oxidation of sulfides to the corresponding sulfones with magnesium monoperoxyphthalate on hydrated silica gel has been developed.
A new methodology for obtaining α-oxo ester equivalents: Sulfanylation of α-sulfonyl carboxylic esters in a solid/liquid phase transfer catalytic system
Wladislaw, Blanka,Marzorati, Liliana,Junior, Nelson Ferreira Claro,Di Vitta, Claudio
, p. 420 - 422 (2007/10/03)
A new, convenient procedure for the synthesis of a wide range of α-methylsulfanyl-α-phenylsulfonyl carboxylic esters has been developed and their facile conversion to the corresponding α-oxo esters demonstrated.
α-Fluorination of methyl phenyl sulfoxide and related compounds by molecular fluorine: A novel method for the introduction of fluorine into sulfoxides bearing α-H atoms
Toyota, Akemi,Ono, Yoshinori,Chiba, Jun,Sugihara, Takumichi,Kaneko, Chikara
, p. 703 - 708 (2007/10/03)
Direct formation of α-fluorosulfones from sulfoxides bearing α-H atoms merely by reaction with molecular fluorine (5% F2/N2) is reported, and a novel non-Pummerer-type mechanism is proposed for this α-fluorination reaction.
