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.
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.
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.
REACTIONS OF TERMINAL ACETYLENES WITH ARYL IODIDES CATALYZED BY PALLADIUM COMPLEXES UNDER INTERFACIAL CONDITIONS
Bumagin, N. A.,Ponomarev, A. B.,Ryabtsev, A. N.,Beletskaya, I. P.
, p. 507 - 509 (1988)
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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.
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.
Photoredox synthesis of functionalized quinazolinesviacopper-catalyzed aerobic oxidative Csp2-H annulation of amidines with terminal alkynes
Charpe, Vaibhav Pramod,Hwang, Kuo Chu,Ragupathi, Ayyakkannu,Sagadevan, Arunachalam
supporting information, p. 5024 - 5030 (2021/07/29)
We have developed a visible light-induced photo-redox copper-catalyzed oxidative Csp2-H annulation (Friedel-Crafts-type cyclization) of amidines with terminal alkynes at room temperature to synthesize functionalized quinazolines. We report copp
Design, Synthesis, and Bioactivities of Phthalide and Coumarin Derivatives Based on the Biosynthesis and Structure Simplification of Gossypol
Guo, Zhonglin,Zhou, Pan,Song, Hongjian,Liu, Yuxiu,Zhang, Jingjing,Li, Yongqiang,Wang, Qingmin
, p. 15123 - 15135 (2021/12/27)
Because gossypol and hemigossypol show antiviral activity but are structurally complex, we designed and synthesized a series of structurally simpler phthalide and coumarin derivatives. The phthalide derivatives were synthesized by opening the naphthalene ring of hemigossypol, and the coumarin derivatives were synthesized by ring-opening reactions of the phthalide derivatives with the goal of investigating the effect of the lactone ring size on bioactivity. The bioassay results showed that the two series of target compounds possessed moderate to good activities against tobacco mosaic virus, One of the compounds showed in vivo inactivation, curative, and protection activities of 50 ± 1, 53 ± 3, and 48 ± 2% at 500 mg/L, values which are higher than those of gossypol (32 ± 1, 35 ± 1, 29 ± 1%, respectively) and comparable to those of hemigossypol (55 ± 1, 49 ± 1, and 48 ± 1%, respectively) and the commercial antiviral agent ningnanmycin (56 ± 2, 54 ± 1, 58 ± 1%) at the same dose. Thus, this compound is a promising candidate for the development of new anti-plant-virus agents. In addition, most of the synthesized compounds showed broad-spectrum activity when tested against 14 kinds of phytopathogenic fungi and showed selectivity against Sclerotinia sclerotiorum, Physalospora piricola, and Rhizoctonia cerealis. Moreover, some of the compounds exhibited activity against Plutella xylostella larvae; the two most active compounds exhibited larvicidal activities (LC50) of 4.10 and 5.47 mg/L, respectively. Further studies showed that these compounds also exhibited insecticidal activities against Mythimna separata, Helicoverpa armigera, and Pyrausta nubilalis larvae.
