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Search for "copper catalysts" in Full Text gives 55 result(s) in Beilstein Journal of Organic Chemistry.

Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination

  • Jiyun Sun,
  • Xiaohua Zhen,
  • Huaibin Ge,
  • Guangtao Zhang,
  • Xuechan An and
  • Yunfei Du

Beilstein J. Org. Chem. 2018, 14, 1452–1458, doi:10.3762/bjoc.14.123

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  • higher temperature was unsuccessful (Table 1, entry 7). Replacing the catalyst CuI with other commonly used copper catalysts including CuCl, CuBr and CuOAc led to a decreased yield in each case (Table 1, entries 8–10). In addition the other commonly employed hypervalent iodine(III) reagents, namely, PIDA
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Published 15 Jun 2018

CF3SO2X (X = Na, Cl) as reagents for trifluoromethylation, trifluoromethylsulfenyl-, -sulfinyl- and -sulfonylation. Part 1: Use of CF3SO2Na

  • Hélène Guyon,
  • Hélène Chachignon and
  • Dominique Cahard

Beilstein J. Org. Chem. 2017, 13, 2764–2799, doi:10.3762/bjoc.13.272

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Published 19 Dec 2017

Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole

  • Martina Tireli,
  • Silvija Maračić,
  • Stipe Lukin,
  • Marina Juribašić Kulcsár,
  • Dijana Žilić,
  • Mario Cetina,
  • Ivan Halasz,
  • Silvana Raić-Malić and
  • Krunoslav Užarević

Beilstein J. Org. Chem. 2017, 13, 2352–2363, doi:10.3762/bjoc.13.232

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  • mechanochemical CuAAC reactions, indicating that the catalysis is most likely conducted on the surface of milling balls. Electron spin resonance spectroscopy was used to determine the oxidation and spin states of the respective copper catalysts in bulk products obtained by milling procedures. Keywords: electron
  • solution, but these reactions are usually much slower [31]. Also, click polymerization was applied using a ball-milling process with no significant influence on the integrity of the polymer chain [27][32]. Herein we have studied the efficiency of copper catalysts with Cu(0), Cu(I) and Cu(II) oxidation
  • advanced Raman techniques such as shifted-excitation Raman difference spectroscopy (SERDS) could be possible [52]. In this way, mechanistic details of these reactions and the behavior of all studied copper catalysts may be more visible, opening the path towards elucidation of mechanism(s) for the solvent
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Published 06 Nov 2017

Direct catalytic arylation of heteroarenes with meso-bromophenyl-substituted porphyrins

  • Alexei N. Kiselev,
  • Olga K. Grigorova,
  • Alexei D. Averin,
  • Sergei A. Syrbu,
  • Oskar I. Koifman and
  • Irina P. Beletskaya

Beilstein J. Org. Chem. 2017, 13, 1524–1532, doi:10.3762/bjoc.13.152

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  • benzothiazole, benzoxazole, N-methylbenzimidazole and caffeine. Plausible action of palladium and copper catalysts with transmetalation step. Dirylation of zinc di-meso-(bromophenyl)porphyrinates 10–12 with benzothiazole, benzoxazole and N-methyl benzimidazole. Polyarylation of zinc tetrakis-meso-(bromophenyl
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Published 03 Aug 2017

Transition-metal-catalyzed synthesis of phenols and aryl thiols

  • Yajun Liu,
  • Shasha Liu and
  • Yan Xiao

Beilstein J. Org. Chem. 2017, 13, 589–611, doi:10.3762/bjoc.13.58

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  • for the synthesis of phenols. In the beginning, palladium catalysts have attracted much attention due to their high conversion efficiency, and later copper catalysts, which are cheaper and more stable, have been extensively studied in this field. 1.1.1 Palladium-catalyzed hydroxylation of aryl halides
  • phenols in water at room temperature. This catalyst can be reused many times without loss of the catalytic activity. Moreover, this catalyst could also be applied in the synthesis of anilines. 1.1.2 Copper-catalyzed hydroxylation of aryl halides: Copper catalysts are considered as economical and stable
  • catalysts. However, copper catalysts often have a low catalytic activity to activate the C–Hal bond. Fortunately, along with the development of various bidentate ligands, the copper-catalyzed C–O coupling reaction has been extensively applied in the synthesis of phenols from aryl halides. However, the
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Published 23 Mar 2017

Copper-catalyzed asymmetric sp3 C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst

  • Pierre Querard,
  • Inna Perepichka,
  • Eli Zysman-Colman and
  • Chao-Jun Li

Beilstein J. Org. Chem. 2016, 12, 2636–2643, doi:10.3762/bjoc.12.260

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  • , St Andrews, Fife, KY16 9ST, UK 10.3762/bjoc.12.260 Abstract This report describes a highly enantioselective oxidative sp3 C–H arylation of N-aryltetrahydroisoquinolines (THIQs) through a dual catalysis platform. The combination of the photoredox catalyst, [Ir(ppy)2(dtbbpy)]PF6, and chiral copper
  • catalysts provide a mild and highly effective sp3 C–H asymmetric arylation of THIQs. Keywords: C–H arylation; copper catalyst; enantioselectivity; visible light; Introduction Functionalization of sp3 C–H bonds is a unique and powerful transformation in modern organic synthesis, which remains a challenging
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Published 06 Dec 2016

Palladium-catalyzed ring-opening reactions of cyclopropanated 7-oxabenzonorbornadiene with alcohols

  • Katrina Tait,
  • Oday Alrifai,
  • Rebecca Boutin,
  • Jamie Haner and
  • William Tam

Beilstein J. Org. Chem. 2016, 12, 2189–2196, doi:10.3762/bjoc.12.209

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  • the use of platinum catalysts [19] or palladium catalysts with zinc co-catalyst with phenol nucleophiles [20]. Meanwhile, anti-stereoisomeric products 5 and 6 are obtained when copper catalysts are used with alkyl nucleophiles [21], if rhodium [22] or iridium catalysts are used in the presence of
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Published 14 Oct 2016

Catalytic Chan–Lam coupling using a ‘tube-in-tube’ reactor to deliver molecular oxygen as an oxidant

  • Carl J. Mallia,
  • Paul M. Burton,
  • Alexander M. R. Smith,
  • Gary C. Walter and
  • Ian R. Baxendale

Beilstein J. Org. Chem. 2016, 12, 1598–1607, doi:10.3762/bjoc.12.156

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  • protocols it is clear that the use of sub-stoichiometric amounts of the copper catalysts presents an advantage over the stoichiometric amount used in the original flow studies [13]. Additionally, the use of oxygen as the oxidant offers improved atom economy over the use of systems such as TEMPO and tert
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Published 26 Jul 2016

Catalytic asymmetric synthesis of biologically important 3-hydroxyoxindoles: an update

  • Bin Yu,
  • Hui Xing,
  • De-Quan Yu and
  • Hong-Min Liu

Beilstein J. Org. Chem. 2016, 12, 1000–1039, doi:10.3762/bjoc.12.98

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  • tolerance were observed. However, no reaction occurred between the ortho-chloro substituted 1,3-diaryl-2-propenyl acetate and 3-O-Boc-oxindole because the chlorine atom inhibited the formation of the active π-allyl-palladium species. Cu-catalyzed direct addition The copper catalysts have gained an
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Published 18 May 2016

Copper-catalyzed aminooxygenation of styrenes with N-fluorobenzenesulfonimide and N-hydroxyphthalimide derivatives

  • Yan Li,
  • Xue Zhou,
  • Guangfan Zheng and
  • Qian Zhang

Beilstein J. Org. Chem. 2015, 11, 2721–2726, doi:10.3762/bjoc.11.293

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  • . The aminooxygenation product could be converted into the corresponding alcohol or free amine through the cleavage of the N–O or C–N bond of the N-hydroxyphthalimide moiety. Keywords: aminooxygenation of styrenes; copper catalysts; N-fluorobenzenesulfonimide; N-hydroxyphthalimide derivatives
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Published 24 Dec 2015

Enantioselective additions of copper acetylides to cyclic iminium and oxocarbenium ions

  • Jixin Liu,
  • Srimoyee Dasgupta and
  • Mary P. Watson

Beilstein J. Org. Chem. 2015, 11, 2696–2706, doi:10.3762/bjoc.11.290

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  • -based catalysts [9][10][11][12][13][14][15]. Among these, chiral copper catalysts have been used with remarkable success in the alkynylation of cyclic iminium ion and oxocarbenium ion intermediates. This review will focus on the development of these enantioselective, copper-catalyzed alkynylations
  • are not possible. Conditions to enable the use of non-stabilized iminium and oxocarbenium ions with β-hydrogens would represent an exceptional advance in this field and allow access to a wide variety of useful compounds. In addition, little is understood about how these chiral copper catalysts provide
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Published 22 Dec 2015

A concise and efficient synthesis of benzimidazo[1,2-c]quinazolines through CuI-catalyzed intramolecular N-arylations

  • Xinlong Pang,
  • Chao Chen,
  • Ming Li and
  • Chanjuan Xi

Beilstein J. Org. Chem. 2015, 11, 2365–2369, doi:10.3762/bjoc.11.258

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  • -cyanoaniline (1) and diaryliodonium salts 2 based on our previously published method [13][14] (Scheme 1). Results and Discussion During the study of the synthesis of various carbocycles or heterocycles with copper catalysts [13][14][15][16][17], we found an interesting tandem reaction of o-cyanoanilines 1 and
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Published 30 Nov 2015

Recent developments in copper-catalyzed radical alkylations of electron-rich π-systems

  • Kirk W. Shimkin and
  • Donald A. Watson

Beilstein J. Org. Chem. 2015, 11, 2278–2288, doi:10.3762/bjoc.11.248

Graphical Abstract
  • for the reaction. These types of ligands in conjunction with copper catalysts are known to promote the formation of stabilized carbon-centered radicals [14]. In this reaction, the putative tertiary radical undergoes addition to a styrene derivative, creating a stabilized benzylic radical. Akin to
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Published 23 Nov 2015

Recent advances in copper-catalyzed C–H bond amidation

  • Jie-Ping Wan and
  • Yanfeng Jing

Beilstein J. Org. Chem. 2015, 11, 2209–2222, doi:10.3762/bjoc.11.240

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  • to be capable of catalyzing the C–H amidation reactions, copper is particularly advantageous because of the low cost, low toxicity and broad tolerance of copper catalysts. Therefore, the present review summarizes the advances on the copper-catalyzed C–H activation-based amidation (including related
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Published 17 Nov 2015

C–H bond halogenation catalyzed or mediated by copper: an overview

  • Wenyan Hao and
  • Yunyun Liu

Beilstein J. Org. Chem. 2015, 11, 2132–2144, doi:10.3762/bjoc.11.230

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  • , significant advances have also occurred in the C–H halogenation catalyzed by different transition metals as Pd [19][20][21][22][23], Rh [24][25], Ru [26], Au [27], Co [28], etc. As a class of readily available and ubiquitously employed transition metal catalysts, copper catalysts have exhibited tremendous
  • practical application of these metal-free methods. The application of copper catalysts was found as effective solution to some of these problems. For example, Wu et al. [70] reported the efficient synthesis of α-iodoketals 76 and 77 via CuO-mediated selective mono-iodination of diketones 74 and
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Published 09 Nov 2015

Effective ascorbate-free and photolatent click reactions in water using a photoreducible copper(II)-ethylenediamine precatalyst

  • Redouane Beniazza,
  • Natalia Bayo,
  • Florian Molton,
  • Carole Duboc,
  • Stéphane Massip,
  • Nathan McClenaghan,
  • Dominique Lastécouères and
  • Jean-Marc Vincent

Beilstein J. Org. Chem. 2015, 11, 1950–1959, doi:10.3762/bjoc.11.211

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  • , F-38000 Grenoble, France Univ. Bordeaux, IECB, UMS 3033/US 001, 2 rue Escarpit, 33607 Pessac, France CNRS, IECB, UMS 3033, 33600 Pessac, France INSERM, IECB, US 001, 33600 Pessac, France 10.3762/bjoc.11.211 Abstract The search for copper catalysts able to perform effectively click reactions in
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Published 21 Oct 2015

Cross-dehydrogenative coupling for the intermolecular C–O bond formation

  • Igor B. Krylov,
  • Vera A. Vil’ and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2015, 11, 92–146, doi:10.3762/bjoc.11.13

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Published 20 Jan 2015

A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline

  • Chunpu Li,
  • Lei Zhang,
  • Shuangjie Shu and
  • Hong Liu

Beilstein J. Org. Chem. 2014, 10, 2441–2447, doi:10.3762/bjoc.10.254

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  • convenient methods to prepare nitrogen-containing tetracyclic compounds incorporating the bioactive indole motif in organic chemistry and medicinal chemistry. Over the past decades, copper catalysts have been proven highly powerful for various cross-coupling reactions, including Ullmann-type couplings of
  • copper catalysts were screened at 80 °C using L-proline as ligand, and K2CO3 as base in a mixed solvent of DMSO and H2O (volume ratio 1:1) (Table 1, entries 1–4). To our delight, the desired product 4a was obtained in 36% yield using CuI as catalyst and 50% yield with Cu2O (Table 1, entries 1 and 4
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Published 21 Oct 2014

Direct C–H trifluoromethylation of di- and trisubstituted alkenes by photoredox catalysis

  • Ren Tomita,
  • Yusuke Yasu,
  • Takashi Koike and
  • Munetaka Akita

Beilstein J. Org. Chem. 2014, 10, 1099–1106, doi:10.3762/bjoc.10.108

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  • application to the synthesis of tetrasubstituted CF3-alkenes is not well documented (Scheme 2b) [63][64]. Another straightforward approach is direct C–H trifluoromethylation of alkenes (Scheme 2c). The groups of Loh, Besset, Cahard, Sodeoka and Xiao showed that copper catalysts can induce a C–H
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Published 12 May 2014

Copper–phenanthroline catalysts for regioselective synthesis of pyrrolo[3′,4′:3,4]pyrrolo[1,2-a]furoquinolines/phenanthrolines and of pyrrolo[1,2-a]phenanthrolines under mild conditions

  • Rupankar Paira,
  • Tarique Anwar,
  • Maitreyee Banerjee,
  • Yogesh P. Bharitkar,
  • Shyamal Mondal,
  • Sandip Kundu,
  • Abhijit Hazra,
  • Prakas R. Maulik and
  • Nirup B. Mondal

Beilstein J. Org. Chem. 2014, 10, 692–700, doi:10.3762/bjoc.10.62

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  • summarized in Table 1, revealed the supremacy of copper catalysts in this particular reaction over the others; CuCl2 appeared to be the catalyst of choice (Table 1, entries 8–32). In order to explore the effect of ligands, a number of phosphines, bis-oxazocines, pyrazolyl-pyrimidines and phenanthroline
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Published 20 Mar 2014

Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira–Glaser cyclization sequence

  • Fabian Klukas,
  • Alexander Grunwald,
  • Franziska Menschel and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2014, 10, 672–679, doi:10.3762/bjoc.10.60

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  • under microwave heating (the temperature optimum of 130 °C was quickly identified by screening experiments), the water/KOH ratio, and the concentrations were varied. In the course of our studies a related work using copper catalysts with the electronrich DMEDA (N,N’-dimethylethylenediamine) or the
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Published 18 Mar 2014

Boron-substituted 1,3-dienes and heterodienes as key elements in multicomponent processes

  • Ludovic Eberlin,
  • Fabien Tripoteau,
  • François Carreaux,
  • Andrew Whiting and
  • Bertrand Carboni

Beilstein J. Org. Chem. 2014, 10, 237–250, doi:10.3762/bjoc.10.19

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  • and co-workers described metal-catalysed tandem Diels–Alder/hydrolysis reactions of 2-boron-substituted 1,3-dienes [54][55]. Boron-dienes containing various ligands reacted with maleimides in the presence of rhodium and copper catalysts using BINAP as ligand (Scheme 15). NMR analysis of the crude
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Published 22 Jan 2014

Advancements in the mechanistic understanding of the copper-catalyzed azide–alkyne cycloaddition

  • Regina Berg and
  • Bernd F. Straub

Beilstein J. Org. Chem. 2013, 9, 2715–2750, doi:10.3762/bjoc.9.308

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Published 02 Dec 2013

Microwave-assisted synthesis of 5,6-dihydroindolo[1,2-a]quinoxaline derivatives through copper-catalyzed intramolecular N-arylation

  • Fei Zhao,
  • Lei Zhang,
  • Hailong Liu,
  • Shengbin Zhou and
  • Hong Liu

Beilstein J. Org. Chem. 2013, 9, 2463–2469, doi:10.3762/bjoc.9.285

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  • stoichiometric quantities of copper catalyst and low to moderate yields [20]. A recent breakthrough to overcome these drawbacks involves the use of appropriate ligands such as diamines and amino acids [21][22][23][24] that can enhance the activity of the copper catalysts and accelerate the reactions. As a result
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Published 14 Nov 2013

Gold(I)-catalyzed formation of furans from γ-acyloxyalkynyl ketones

  • Marie Hoffmann,
  • Solène Miaskiewicz,
  • Jean-Marc Weibel,
  • Patrick Pale and
  • Aurélien Blanc

Beilstein J. Org. Chem. 2013, 9, 1774–1780, doi:10.3762/bjoc.9.206

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  • latter have already been described to rearrange into furans by using copper catalysts. Indeed, Gevorgyan et al. showed that the combination of copper(I) chloride and triethylamine catalyzed the 1,2-migration/cycloisomerization of γ-acyloxyalkynyl ketones in dimethylacetamide (DMA) at 130 °C (Scheme 2
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Published 30 Aug 2013
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