7515-23-3Relevant articles and documents
Synthesis method of aryl-substituted alkyne
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Paragraph 0031-0035, (2021/10/20)
The invention relates to the technical field of synthesis of aryl substituted alkyne, and discloses a synthetic method of an aryl-substituted alkyne, and discloses a synthesis method of an aryl-substituted alkyne. Aryl boronic acid and divalent copper compounds, 8 - hydroxyquinoline, an oxidizing agent and an inorganic base are added to the reaction solvent, and the aryl substituted alkyne is obtained by stirring and separating after stirring at room temperature. Compared with the existing sonogashira reaction, the synthesis method disclosed by the invention realizes the aryl reaction of the lean electron alkyne through the oxidative coupling reaction, avoids Sonogashira reaction required precious palladium catalyst, can react at room temperature, and is mild in reaction condition and high in product yield.
Enantioselective Fluorination of α-Branched β-Ynone Esters Using a Cinchona-Based Phase-Transfer Catalyst
Arimitsu, Satoru,Iwasa, Satsuki,Arakaki, Ryunosuke
supporting information, p. 12804 - 12812 (2020/10/09)
Herein, we report the fluorination of α-branched β-ynone esters to afford their corresponding quaternary fluorinated products with good enantioselectivity (ee = 73-90%) using a cinchona-based phase-transfer catalyst. α-Branched β-ynone esters possess a highly acidic α-proton and form their corresponding enolate as a single isomer, which allows the enantioselective fluorination reaction to occur under standard cinchona-based phase-transfer catalyst conditions. Moreover, the obtained α-fluorinated product can be treated with [(SPhos)AuNTf2] (1 mol %) to afford a fluorinated 3,5-diketo carboxylic acid.
Oxidant- and additive-free simple synthesis of 1,1,2-triiodostyrenes by one-pot decaroboxylative iodination of propiolic acids
Ghosh, Subhankar,Ghosh, Rajat,Chattopadhyay, Shital K.
supporting information, (2020/09/15)
A metal- and oxidant-free facile synthesis of a range of 1,1,2-triiodostryrene derivatives has been developed which utilizes a simple decarboxylative triiodination of propiolic acids using molecular iodine and sodium acetate in a one-pot manner. Electron-
Synthesis of 1-Amino-2 H-quinolizin-2-one Scaffolds by Tandem Silver Catalysis
Min, Xiao-Long,Sun, Chao,He, Ying
supporting information, p. 724 - 728 (2019/02/21)
An efficient tandem cycloisomerization-amination reaction catalyzed by silver is described. This rapid and atom-economic reaction delivered 1-amino-2H-quinolizin-2-one scaffolds in high yields under mild conditions. The reaction could be extended to an asymmetric version albeit with moderate enantioselective excess of the products. In addition, the products can be easily reduced into various azabicycles containing 4-pyridones, which are important building blocks in organic synthesis.
Cobalt(III)-Catalyzed Intermolecular Carboamination of Propiolates and Bicyclic Alkenes via Non-Annulative Redox-Neutral Coupling
Zhu, Yuelu,Chen, Feng,Zhao, Xinyang,Yan, Dingyuan,Yong, Wanxiong,Zhao, Jing
supporting information, p. 5884 - 5888 (2019/08/20)
A cobalt(III)-catalyzed, redox-neutral, intermolecular carboamination of propiolates and bicyclic alkenes was developed. This non-annulative coupling strategy features atom economy, high regioselectivity, good yields, and functional groups tolerance. Such a carboamination reaction was applied to modified phenols from the corresponding phenols under mild conditions.
Transition Metal-Free Trans Hydroboration of Alkynoic Acid Derivatives: Experimental and Theoretical Studies
Fritzemeier, Russell,Gates, Ashley,Guo, Xueying,Lin, Zhenyang,Santos, Webster L.
, p. 10436 - 10444 (2018/07/21)
We report a phosphine-catalyzed trans hydroboration of alkynoate esters and amides. The reaction proceeds under mild conditions with exclusive (E)-selectivity to afford (E)-β-boryl acrylates and (E)-β-boryl acrylamides in good to excellent yields. The reaction is tolerant of a variety of functional groups and allows efficient access to novel oxaboroles as well as a pargyline derivative (MAO inhibitor). Theoretical calculations suggest an internal hydride generates a phosphonium allenoxyborane followed by the formation of a key phosphonocyclobutene intermediate that collapses in a stereoselective, rate-limiting step.
Rhodium(III)-Catalyzed Redox-Neutral Cascade [3 + 2] Annulation of N-Phenoxyacetamides with Propiolates via C-H Functionalization/Isomerization/Lactonization
Pan, Jin-Long,Chen, Chao,Hao, Yu,Liu, Chang,Bai, He-Yuan,Ding, Jun,Zhang, Shu-Yu,Wang, Li-Ren,Xie, Peipei,Xia, Yuanzhi
supporting information, p. 7131 - 7136 (2018/12/14)
A Rh(III)-catalyzed cascade [3 + 2] annulation of N-phenoxyacetamides with propiolates under mild conditions using the internal oxidative O-N bond as the directing group has been achieved. This catalytic system provides a regio- and stereoselective access to benzofuran-2(3H)-ones bearing exocyclic enamino motifs with exclusive Z configuration selectivity, acceptable to good yields and good functional group compatibility. Mechanistic investigations by experimental and density functional theory studies suggest that a consecutive process of C-H functionalization/isomerization/lactonization is likely to be involved in the reaction.
Salt-Free Strategy for the Insertion of CO2 into C?H Bonds: Catalytic Hydroxymethylation of Alkynes
Wendling, Timo,Risto, Eugen,Krause, Thilo,Goo?en, Lukas J.
supporting information, p. 6019 - 6024 (2018/03/27)
A copper(I) catalyst enables the insertion of carbon dioxide into alkyne C?H bonds by using a suitable organic base with which hydrogenation of the resulting carboxylate salt with regeneration of the base becomes thermodynamically feasible. In the presence of catalytic copper(I) chloride/4,7-diphenyl-1,10-phenanthroline, polymer-bound triphenylphosphine, and 2,2,6,6-tetramethylpiperidine as the base, terminal alkynes undergo carboxylation at 15 bar CO2 and room temperature. After filtration, the ammonium alkynecarboxylate can be hydrogenated to the primary alcohol and water at a rhodium/molybdenum catalyst, regenerating the amine base. This demonstrates the feasibility of a salt-free overall process, in which carbon dioxide serves as a C1 building block in a C?H functionalization.
Preparation of 1-aryl-2-bromo-3,3-difluorocyclopropenes
Lin, Shaw-Tao,Chen, Li-Chwen,Lee, Chun-Jen
, p. 353 - 355 (2007/10/03)
1-Aryl-2-bromo-3,3-difluorocyclopropanes were prepared from the reaction of 2′,2′-difluorostyrene and dibromocarbene instead of from 1-aryl-2-haloacetylenes and difluorocarbene. These results are rationalised by the energy gap between HOMO(styrene), HOMO(acetylene) and LUMO(CX2). The title compounds were converted to methyl arylpropynoate in MeOH solution in quantitative yield.
