62708-42-3Relevant academic research and scientific papers
Nickel-Catalyzed Intramolecular Hydroalkenylation of Imines
Feng, Wei-Min,Li, Tian-Yu,Xiao, Li-Jun,Zhou, Qi-Lin
supporting information, p. 7900 - 7904 (2021/10/12)
A ligand-enabled nickel-catalyzed intramolecular hydroalkenylation of imines with unactivated alkenes has been developed. A variety of five- and six-membered cyclic allylic amines were synthesized in high yields. The use of both wide-bite-angle diphosphine ligand and Br?nsted acid is crucial for realizing the reaction. Preliminary investigation of the asymmetric intramolecular hydroalkenylation of imines shows promising potential for the application of the method in the synthesis of enantio-enriched cyclic allylic amines.
Synthetic method of flavonoid compound containing CMe2CF3 group
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Paragraph 0026; 0037-0038, (2020/06/17)
The invention belongs to the field of chemical synthesis, and particularly relates to a synthetic method of a flavonoid compound containing a CMe2CF3 group; the synthetic method has the characteristics of simple operation, good functional group compatibility and the like, and the flavonoid compound containing the CMe2CF3 group and obtained by reaction has a wide application prospect.
Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation–cyclization cascade mediated by K2S2O8
Liu, Qiang,Lu, Weibang,Wang, Xiaoxia,Xie, Guanqun
supporting information, p. 1974 - 1982 (2020/10/02)
A variety of chroman-4-ones bearing phosphine oxide motifs were conveniently synthesized from readily available diphenylphosphine oxides and alkenyl aldehydes via a metal-free tandem phosphinoylation/cyclization protocol. The reaction utilizes K2S2O8 as oxidant and proceeds in DMSO/H2O at environmentally benign conditions with a broad substrate scope and afforded the title compounds in moderate yields.
Palladium-Catalyzed Intramolecular Mizoroki-Heck-Type Reaction of Diarylmethyl Carbonates
Matsude, Akihiro,Hirano, Koji,Miura, Masahiro
, p. 518 - 522 (2019/12/24)
A palladium-catalyzed intramolecular Mizoroki-Heck-type reaction of diarylmethyl tert-butyl carbonates has been developed. The reaction proceeds under external base-free, neutral conditions to form the corresponding methyleneindanes in good yields only with liberation of CO2 and tBuOH. The resulting exo-methylene moiety is reactive and thus a good synthetic handle for further manipulations. Additionally, the asymmetric synthesis is also possible through a Pd/chiral Mandyphos ligand-mediated kinetic resolution. To the best of our knowledge, this is the first successful example of catalytic enantioselective Mizoroki-Heck-type reaction of secondary benzyl electrophiles. (Figure presented.).
"Close-to-Release": Spontaneous Bioorthogonal Uncaging Resulting from Ring-Closing Metathesis
Sabatino, Valerio,Rebelein, Johannes G.,Ward, Thomas R.
supporting information, p. 17048 - 17052 (2019/10/11)
Bioorthogonal uncaging reactions offer versatile tools in chemical biology. In recent years, reactions have been developed to proceed efficiently under physiological conditions. We present herein an uncaging reaction that results from ring-closing metathesis (RCM). A caged molecule, tethered to a diolefinic substrate, is released via spontaneous 1,4-elimination following RCM. Using this strategy, which we term "close-to-release", we show that drugs and fluorescent probes are uncaged with fast rates, including in the presence of mammalian cells or in the periplasm of Escherichia coli. We envision that this tool may find applications in chemical biology, bioengineering and medicine.
Cobalt-catalyzed cyclization with the introduction of cyano, acyl and aminoalkyl groups
Hori, Hiroto,Arai, Shigeru,Nishida, Atsushi
supporting information, p. 4783 - 4788 (2019/05/24)
An efficient synthesis of carbo-and heterocycles using CC, CO and CN bonds under cobalt catalysis is described. The substituents on olefins are key for controlling the regio-and chemoselectivity in the initial hydrogen atom transfer step and quaternary carbons are efficiently constructed under mild conditions. Cyclopropane cleavage and tandem cyclization give highly functionalized bicyclic skeletons in a single operation.
Copper-Catalyzed Cope-Type Hydroamination of Nonactivated Olefins toward Cyclic Nitrones: Scope, Mechanism, and Enantioselective Process Development
Zhang, Mengru,Liu, Shuang,Li, Hexin,Guo, Yajing,Li, Na,Guan, Meihui,Mehfooz, Haroon,Zhao, Jinbo,Zhang, Qian
, p. 12620 - 12627 (2019/09/16)
The catalytic synthesis of cyclic nitrones, an important type of functional molecules for both synthetic chemistry and related fields, remains underdeveloped. Herein we report the copper-catalyzed Cope-type hydroamination of oximes with pendant nonactivated olefins, which enables facile access to a series of five- and six-membered cyclic nitrones under mild conditions. In this study, heterocycle-tethered oximes were employed in the Cope-type hydroamination reaction for the first time. High enantioselectivity was achieved for carbon-tethered γ,δ-vinyl oximes to afford enantioenriched five-membered cyclic nitrones. The results of preliminary mechanistic studies indicate a mononuclear catalytic species and a unified catalytic pathway over a large temperature range.
Synthesis of chroman-4-one and indanone derivatives via silver catalyzed radical ring opening/coupling/cyclization cascade
Liu, Qiang,Xie, Guanqun,Wang, Qiang,Mo, Zhendong,Li, Chen,Ding, Shujiang,Wang, Xiaoxia
, (2019/09/10)
A variety of chroman-4-one and indanone derivatives were conveniently synthesized from readily available cyclopropanols and alkenyl aldehydes via a silver catalyzed radical ring-opening/coupling/cyclization cascade. The reaction proceeded under mild and neutral conditions with broad substrate scope and afforded the desired products in moderate to good yields. A probable mechanism for the cascade reaction was also proposed.
Ni-Catalyzed Carbon-Carbon Bond-Forming Reductive Amination
Heinz, Christoph,Lutz, J. Patrick,Simmons, Eric M.,Miller, Michael M.,Ewing, William R.,Doyle, Abigail G.
supporting information, p. 2292 - 2300 (2018/02/19)
This report describes a three-component, Ni-catalyzed reductive coupling that enables the convergent synthesis of tertiary benzhydryl amines, which are challenging to access by traditional reductive amination methodologies. The reaction makes use of iminium ions generated in situ from the condensation of secondary N-trimethylsilyl amines with benzaldehydes, and these species undergo reaction with several distinct classes of organic electrophiles. The synthetic value of this process is demonstrated by a single-step synthesis of antimigraine drug flunarizine (Sibelium) and high yielding derivatization of paroxetine (Paxil) and metoprolol (Lopressor). Mechanistic investigations support a sequential oxidative addition mechanism rather than a pathway proceeding via α-amino radical formation. Accordingly, application of catalytic conditions to an intramolecular reductive coupling is demonstrated for the synthesis of endo- and exocyclic benzhydryl amines.
Synthesizing method of indanone compound
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Paragraph 0090-0092, (2018/11/04)
The invention discloses a synthesizing method of an indanone compound. The synthesizing method comprises the following steps of respectively adding a catalyst and an antioxidant into a reaction bottle, then adding a compound shown in a formula (2), adding a solvent, and reacting for 2 to 6h at the temperature of 70 to 120 DEG C under the argon protection atmosphere, so as to obtain the indanone compound, wherein the catalyst is selected from any one of Cu(OAc)2, CuCl2 (copper (II) chloride), CuBr2 (copper (II) bromide), CuO (copper oxide), CuF2 (copper fluoride), Cu(OTf) 2, Cu(OH)2 (copper hydroxide), Cu(NO3)2 (copper nitrate), CuCl (copper chloride), CuBr (copper bromide), CuI (cuprous iodide) and Cu2O (cuprous oxide); the oxidant is tert-butyl hydroperoxide; the solvent is toluene. The synthesizing method has the advantages that a novel concept of the indanone compound is provided; the copper catalyst is used, the price of copper is low, the reserve amount is rich, the environment-friendly effect is realized, and the hydroacylation reaction catalyzed by copper meets the requirements of green chemistry.
