13146-23-1Relevant articles and documents
Copper-catalyzed annulation of 2-bromobenzoic esters with terminal alkynes towards 3-substituted isocoumarins
Sun, Mengli,Su, Lebin,Dong, Jianyu,Liu, Long,Zhou, Yongbo,Yin, Shuang-Feng
, p. 2433 - 2437 (2017)
An efficient method for the synthesis of 3-substituted isocoumarins that are an important class of biologically active scaffolds via annulation of 2-bromobenzoic esters with terminal alkynes by copper catalyzed is described. The advantages of this method include mild reaction conditions, high yield and regioselectivity, and wide tolerance toward functional groups.
AN EFFICIENT ELECTROCHEMICAL SYNTHESIS OF PHENYLETHYNYLCOPPER(I), C6H5CCCu
Kumar, Rajesh,Tuck, Dennis G.
, p. C47 - C48 (1985)
Phenylethynylcopper(I) can be prepared in high yield by the oxidation of a copper anode in a solution of phenylacetylene in acetone or acetonitrile.This synthesis represents a significant improvement over existing methods.
Photo(electro)catalytic activity enhancement of PhC2Cu by Fe doping induced energy band modulation and luminescence chromism switching
Qian, Jing,Dang, Wenqiang,Li, Jing,Zhang, Wen,Tian, Meng,Wang, Ning,Song, Wenjing,Lv, Lingling,Jiang, Hai-Ying
, p. 2379 - 2385 (2021)
In this work, iron doping was proposed to improve the photo(electro)catalytic activity of PhC2Cu, an air stable metal-organic coordination polymeric photocatalyst. After displacement of partial Cu atoms by Fe, the energy band structure of PhC2Cu was successively modulated, featuring a narrowed band gap and down-shift in the valence band towards a more positive potential. More interestingly, the luminescence chromism upon iron doping is indicative of inhibited ligand-to-metal charge transfer (LMCT) that is relevant to the recombination of photocarriers. When the mole ratio of Fe/Cu reached 2%, the photocurrent density achieved its maximum, which was 4 times higher than that of the PhC2Cu photocathode, consistent with an enhanced separation of electron-hole pairs. Furthermore, the extremely negative conduction band potential of PhC2Cu enabled efficient O2activation, generating a series of reactive oxygen species (ROS) for the degradation of organic pollutants. The rate of methyl orange (MO) and 2,4-dichlorophenol (2,4-DCP) degradation over 2% Fe-PhC2Cu increased by 2 and 1.6 times. This study provides a promising strategy for improving the activity of metal-organic photocatalysts.
A highly stable and versatile heterobifunctional fluoroalkylation reagent for preparation of fluorinated organic compounds
Dai, Jingwen,Li, Zili,Wang, Taisheng,Bai, Ruke
, p. 4382 - 4386 (2016)
A highly stable heterobifunctional fluoroalkylation reagent, 1-azido-2-chloro-1,1,2-trifluoro-2-iodoethane (ACTI) has been prepared in high yield for the first time by a new method. Moreover, the reactivity of both the azido group and the iodine atom of t
Electrochemical preparation and applications of copper(i) acetylides: A demonstration of how electrochemistry can be used to facilitate sustainability in homogeneous catalysis
Seavill, Peter W.,Holt, Katherine B.,Wilden, Jonathan D.
, p. 5474 - 5478 (2018)
Copper(i) acetylides are important intermediates for many syntheses and have been prepared here electrochemically in an energy efficient manner. These were subsequently employed in simple organic C-C bond forming reactions. We also demonstrate that application of Faraday's laws allows the charge to be calculated so that only the required amount of metal is used. In addition, the application of copper-coated graphite electrodes allows the maximum atom efficiency for this process and even offers a recovery strategy to extract the metal following completion of the reaction.
Copper-Catalyzed Decarboxylative Atom Transfer Radical Addition of Iododifluoroacetate to Alkynyl Carboxylic Acids
Li, Gang,Cao, Yi-Xuan,Luo, Chen-Guang,Su, Yi-Ming,Li, Yan,Lan, Quan,Wang, Xi-Sheng
, p. 4806 - 4809 (2016)
The first example of copper-catalyzed decarboxylative atom transfer radical addition of alkynyl carboxylic acids has been developed with a readily available fluoroalkyl halide. This novel protocol has demonstrated a unique difunctionalization of nonterminal alkynes with a broad substrate scope and excellent functional-group tolerance. Mechanistic investigations revealed that the catalytic cycle was initiated by the attack of a difluoroalkyl radical to an in situ generated alkynylcopper species.
Sonogashira reactions of alkyl halides catalyzed by NHC [CNN] pincer nickel(II) complexes
Wang, Zijing,Zheng, Tingting,Sun, Hongjian,Li, Xiaoyan,Fuhr, Olaf,Fenske, Dieter
, p. 11465 - 11470 (2018)
C(carbene)N(amido)N(amine)-pincer nickel(ii) complexes [iPrCNN-Ni-Br] (6), [nBuCNN-Ni-Br] (7) and [BnCNN-Ni-Cl] (8) were synthesized. The catalytic performance of complexes 6-8 for Sonogashira cross-coupling reactions was
Highly selective copper-catalyzed trifunctionalization of alkynyl carboxylic acids: An efficient route to bis-deuterated β-borylated α,β-styrene
Feng, Qiang,Yang, Kai,Song, Qiuling
, p. 15394 - 15397 (2015)
A copper-catalyzed highly efficient protocol for the synthesis of bis-deuterated β-borylated α,β-styrene derivatives, which can be further transformed to practical isotopically labeled compounds, has been developed. Alkynyl carboxylic acids are employed as alkyne synthons yet demonstrate a sharp discrepancy in reactivity and selectivity compared to terminal alkynes. Meanwhile, this reaction offers a novel and efficient strategy for highly selective trifunctionalization of the carbon-carbon triple bond at ambient temperature.
Reaction of alkynylsilanes with CuCl in polar solvents leading to alkynyl group transfer from Si to Cu
Nishihara, Yasushi,Takemura, Miwa,Mori, Atsunori,Osakada, Kohtaro
, p. 282 - 286 (2001)
The reaction of 1-phenyl-2-trimethylsilylethyne with CuCl at 80-100°C in N,N-dimethylformamide (DMF) or N,N-dimethylimidazolidinone (DMI) yielded the alkynylcopper species [Cu2Cl(C≡CPh)]n (1) in 56-63% yields. Heating 1 at 80°C under aerobic conditions gave 1,4-diphenyl-1,3-butadiyne in 82% yield via an oxidative coupling of the phenylethynyl ligands.
The synthesis and biological activity of novel anthracenone-pyranones and anthracenone-furans
Rixson, James E.,Abraham, James R.,Egoshi, Yuki,Skelton, Brian W.,Young, Kelly,Gilbert, Jayne,Sakoff, Jennette A.,Gericke, Kersten M.,McCluskey, Adam,Stewart, Scott G.
, p. 3552 - 3565 (2015)
Abstract An efficient and divergent methodology for the synthesis of new anthracenone-pyranones and anthracenone-furans is described. Key reactions discussed in these syntheses include an aldehyde promoted annulation with a β-keto-sulfoxide, a domino alkyne insertion/carbonylation/Nu-acylation and a DMEDA promoted Castro-Stephens reaction. We also report the in vitro growth inhibition of these compounds in a range of human cancer cells. The natural product BE-26554A displayed good cell growth activity on BE2-C neuroblastoma and SMA glioblastoma cell lines at 0.17 and 0.16 μM (GI50), respectively. Of note, were a CF3 functionalised anthracenone 4-pyranone (chromone) derivative 22, and an anthracenone-furan derivative 54 which displayed 0.20 μM and 0.38 μM growth inhibition, respectively, in the BE2-C neuroblastoma cell line.
