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Search for "CuCl2" in Full Text gives 84 result(s) in Beilstein Journal of Organic Chemistry.

A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids

  • Li Liu,
  • Yue Li,
  • Tiao Huang,
  • Dulin Kong and
  • Mingshu Wu

Beilstein J. Org. Chem. 2021, 17, 2321–2328, doi:10.3762/bjoc.17.150

Graphical Abstract
  • , AlCl3, Cu (CF3SO3)2, and CuCl2, on the reaction was also examined, but no significant improvement in the yield was found (Table 1, entries 17–21). Considering all of the reaction parameters, the optimal reaction conditions were chosen as shown in Table 1, entry 13. Once the optimization studies were
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Published 07 Sep 2021

Synthetic accesses to biguanide compounds

  • Oleksandr Grytsai,
  • Cyril Ronco and
  • Rachid Benhida

Beilstein J. Org. Chem. 2021, 17, 1001–1040, doi:10.3762/bjoc.17.82

Graphical Abstract
  • amines with cyanoguanidine in refluxing water in the presence of CuCl2. The pink copper complexes were then treated with hydrogen sulfide to release the desired compounds. As a representative example, N1-butylbiguanide (buformin) was obtained as a hydrochloride salt, with a 47% yield (Scheme 2). Other
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Published 05 May 2021

Amino- and polyaminophthalazin-1(2H)-ones: synthesis, coordination properties, and biological activity

  • Zbigniew Malinowski,
  • Emilia Fornal,
  • Agata Sumara,
  • Renata Kontek,
  • Karol Bukowski,
  • Beata Pasternak,
  • Dariusz Sroczyński,
  • Joachim Kusz,
  • Magdalena Małecka and
  • Monika Nowak

Beilstein J. Org. Chem. 2021, 17, 558–568, doi:10.3762/bjoc.17.50

Graphical Abstract
  • time intervals of 0 h, 1 h, and 24 h starting from mixing the solutions containing equimolar amounts of the ligand and CuCl2. Unexpectedly, compound 6d (L1) did not show any complexing properties. In all spectra a signal of the same ligand, despite long reaction times, was only observed (ESIMS
  • compound 7 (L3) and CuCl2 showed the presence of two types of complexes containing one and two phthalazinone ligands: [(L3)Cu(II)Cl]+ and [(L3)2Cu2(II)Cl3]+. The most abundant peak at m/z = 422.3 Da corresponded to the complex [(L3)Cu(II)Cl]+. The MS/MS fragmentation of the ions at m/z = 422.3 Da for 63Cu
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Published 25 Feb 2021

4-Hydroxy-3-methyl-2(1H)-quinolone, originally discovered from a Brassicaceae plant, produced by a soil bacterium of the genus Burkholderia sp.: determination of a preferred tautomer and antioxidant activity

  • Dandan Li,
  • Naoya Oku,
  • Yukiko Shinozaki,
  • Yoichi Kurokawa and
  • Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1489–1494, doi:10.3762/bjoc.16.124

Graphical Abstract
  • without test compounds were mixed in 50 mM boric acid/sodium hydroxide buffer (pH 9.0). To this mixture was added CuCl2 (100 μM) to initiate the Fenton reaction, and after 5 min of incubation, the chemiluminescence at 500 nm was recorded on a microplate reader. The experiments were run in triplicate, and
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Published 26 Jun 2020

Synthesis and properties of quinazoline-based versatile exciplex-forming compounds

  • Rasa Keruckiene,
  • Simona Vekteryte,
  • Ervinas Urbonas,
  • Matas Guzauskas,
  • Eigirdas Skuodis,
  • Dmytro Volyniuk and
  • Juozas V. Grazulevicius

Beilstein J. Org. Chem. 2020, 16, 1142–1153, doi:10.3762/bjoc.16.101

Graphical Abstract
  • three-component method was used for the quinazoline formation by refluxing 2-aminobenzophenone, difluorobenzaldehyde, ammonium acetate, and CuCl2 in ethanol. The synthetic method using a cheap catalyst, easy workup, and the high yield (78%) of quinazoline Q1 makes the compound a promising candidate as
  • [14]. A mixture of 2-aminobenzophenone (1.1 g, 5.6 mmol), ammonium acetate (1.3 g, 16.9 mmol), 3,5-difluorobenzaldehyde (0.8 g, 5.6 mmol), and CuCl2 (1.5 g, 11.2 mmol) in 10 cm3 isopropanol was refluxed for 24 h. The progress of the reaction was periodically monitored by thin-layer chromatography
  • . After completion of the reaction, water was added to the mixture until precipitation appeared. The precipitate was collected by filtration and washed with plenty of water to remove excess CuCl2, NH4OAc, and reduced copper salt. Compound Q1 (1.4 g, 78%) was obtained as yellowish crystals. 1H NMR (400 MHz
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Published 28 May 2020

Aldehydes as powerful initiators for photochemical transformations

  • Maria A. Theodoropoulou,
  • Nikolaos F. Nikitas and
  • Christoforos G. Kokotos

Beilstein J. Org. Chem. 2020, 16, 833–857, doi:10.3762/bjoc.16.76

Graphical Abstract
  • yield. The drop in the yield was insignificant in the absence of oxygen. An insignificant drop in the yield was also noticed when an electron scavenger, CuCl2, was added to the reaction mixture, excluding a single electron transfer process. When a triplet state quencher, anthracene, was added, the
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Published 23 Apr 2020

A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions

  • Pezhman Shiri and
  • Jasem Aboonajmi

Beilstein J. Org. Chem. 2020, 16, 551–586, doi:10.3762/bjoc.16.52

Graphical Abstract
  • solid was dispersed in an aqueous solution of CuCl2⋅3H2O for 10 min. The copper species was reduced with an aqueous solution of NaBH4. The metal–dendron SBA-15 material was filtrated, washed with deionized water, and dried to produce x wt % CuYAu–Gx-AAA–SBA-15 (x wt % = weight percent loading of Cu, Y
  • provide an overview on the synthesis and functionalization of carbon nanomaterials the catalytic application of these materials in CuAAC reactions. Very recently, CuCl2 on fabricated graphitic polymeric C3N4-supported CuCl2 (Cu@g-C3N4, 74) was prepared as an off-white bluish solid in two simple steps [76
  • ]. Generally, urea (72) was calcined and then, CuCl2 was immobilized using sonication (Scheme 13). The nanopolymeric catalyst was applied as a reusable nanocatalyst for promoting the 1,3-dipolar cycloaddition of nitroolefins/phenylacetylenes and sodium azide in water at ambient temperature. High yields of the
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Published 01 Apr 2020

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

  • Gagandeep Kour Reen,
  • Ashok Kumar and
  • Pratibha Sharma

Beilstein J. Org. Chem. 2019, 15, 1612–1704, doi:10.3762/bjoc.15.165

Graphical Abstract
  • heterogeneously catalyzed synthesis of imidazo[1,2-a]pyridines from 3 and ketones 20 has been reported (Scheme 7) [101]. Titania-supported CuCl2 (CuCl2/nano TiO2) played the role of catalyst in this transformation under aerobic conditions. Titania support helped in recyclability of the copper salt to four
  • ]. The reaction was initially tried with different catalysts like triflic acid, I2, salts of Pd, Fe, Co and Cu which did not lead to the formation of the final product except CuSO4 and CuCl2 which gave a moderate yield of the products. Further studies revealed CuBr to be the most effective with a maximum
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Published 19 Jul 2019

Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reaction

  • Pierre-Olivier Schwartz,
  • Sebastian Förtsch,
  • Astrid Vogt,
  • Elena Mena-Osteritz and
  • Peter Bäuerle

Beilstein J. Org. Chem. 2019, 15, 1379–1393, doi:10.3762/bjoc.15.138

Graphical Abstract
  • dehydrocoupling with ZnCl2 and CuCl2. Selenophene precursor 10 itself was readily obtained in 68% yield from selenophene (9) in a one-pot procedure by successive lithiation with n-BuLi and quenching with trimethylsilyl chloride and iodine, respectively. We reacted biselenophene 11 with K2S as sulfur source and
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Published 24 Jun 2019

Formation of an unexpected 3,3-diphenyl-3H-indazole through a facile intramolecular [2 + 3] cycloaddition of the diazo intermediate

  • Andrew T. King,
  • Hugh G. Hiscocks,
  • Lidia Matesic,
  • Mohan Bhadbhade,
  • Roger Bishop and
  • Alison T. Ung

Beilstein J. Org. Chem. 2019, 15, 1347–1354, doi:10.3762/bjoc.15.134

Graphical Abstract
  • -butylnitrite, BTEAC and DABSO in the presence of CuCl2 provided an unexpected 3H-indazole product 8. The structure of the compound was determined by HRMS, IR, NMR and further confirmed by single crystal X-ray crystallography. The compound crystallises in the triclinic P-1 space group, with unit cell parameters
  • presence of benzyltriethylammonium chloride (BTEAC) and CuCl2 gave a crude product which was purified by crystallisation from dichloromethane/hexane to give a pale yellow crystalline material in 27% yield. HRMS–ESI analysis produced [M + H]+ m/z 467.2126 corresponding to the formula of C33H27N2O
  • originally present in the diazonium salt. The direct diazotisation of 5 was performed using anhydrous organic solvents and t-BuONO at −10 °C in the presence of CuCl2 (method a) and the classical NaNO2/HCl method b in the absence of CuCl2, as shown in Scheme 3. Compound 8 was obtained in 89% and 96% from
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Published 19 Jun 2019

Synthesis of functionalized diazocines for application as building blocks in photo- and mechanoresponsive materials

  • Widukind Moormann,
  • Daniel Langbehn and
  • Rainer Herges

Beilstein J. Org. Chem. 2019, 15, 727–732, doi:10.3762/bjoc.15.68

Graphical Abstract
  • hydrazine is quite stable towards reduction to the diamine, and can easily be reoxidized to the azo compound using CuCl2/O2. The yields are higher and more reproducible using the above reduction/reoxidation scheme. Previously applied reducing agents include Ba(OH)2/Zn [27], glucose/NaOH [20], Pb/NEt3/HCOOH
  • and 10b are formed, most probably through radical intermediates. Then the dinitro compounds 10a and 10b were reduced with Ba(OH)2/Zn to the hydrazine intermediates and subsequently oxidized with CuCl2 and air in a two-step reductive azo cyclization in a similar manner as described in [27]. After
  • ; iii) Zn, Ba(OH)2 H2O/EtOH, and CuCl2/O2, NaOH/MeOH; iv) Ti(Cl)4, DCM; v) ADMP, DBU, THF; vi) PPh3, H2O, THF; viii) TsCl, DMAP, TEA, DCM, and t-BuOK, THF. Photostationary states (300 K), absorption maxima and half-lives (298.15 K), determined by 1H NMR and UV–vis spectroscopy in acetonitrile
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Published 20 Mar 2019
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  • atmosphere for 2 h. The 3-methyl-1-sulfo-1H-imidazolium metal chlorides [Msim][FeCl4] (3), [Msim][ZnCl3] (4), and [Msim][CuCl2] (5) were examined for the selective synthesis of bis(indolyl)methane derivatives 8 and the results showed that more acidic [Msim][FeCl4] catalyst 3 produces excellent yields of
  • products 8 with only 5 mol % loading. However, 10 mol % of the less acidic [Msim][ZnCl3] (4) and [Msim][CuCl2] (5) catalysts were applied to obtain the desired products 8 with excellent yields (Scheme 1). A recyclability study indicated three consecutive runs with a similar efficiency [38]. Other
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Published 01 Nov 2018

Chiral bisoxazoline ligands designed to stabilize bimetallic complexes

  • Deepankar Das,
  • Rudrajit Mal,
  • Nisha Mittal,
  • Zhengbo Zhu,
  • Thomas J. Emge and
  • Daniel Seidel

Beilstein J. Org. Chem. 2018, 14, 2002–2011, doi:10.3762/bjoc.14.175

Graphical Abstract
  • , possessing an urea backbone, forms a bis-copper complex with two equivalents of CuCl2 (Cu∙∙∙Cu distance = 4.291 Å) [53]. Tetraoxazoline ligand 13 undergoes formation of dinuclear complexes upon treatment with two equivalents of either ZnCl2, Ni(PPh3)2Br2, or Cu(OAc)2 (metal distances: Zn∙∙∙Zn = 8.963 Å; Ni
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Published 01 Aug 2018

Cationic cobalt-catalyzed [1,3]-rearrangement of N-alkoxycarbonyloxyanilines

  • Itaru Nakamura,
  • Mao Owada,
  • Takeru Jo and
  • Masahiro Terada

Beilstein J. Org. Chem. 2018, 14, 1972–1979, doi:10.3762/bjoc.14.172

Graphical Abstract
  • 2-aminophenol derivative 2a (Table 1, entries 3 and 4). Moreover, a cationic copper catalyst generated from CuCl2 and two equivalents of AgSbF6 was effective to afford 2a in good yield (Table 1, entry 5), even at 30 °C (Table 1, entry 8). The use of a ligand, such as 1,10-phenanthroline (phen) and
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Published 31 Jul 2018

β-Hydroxy sulfides and their syntheses

  • Mokgethwa B. Marakalala,
  • Edwin M. Mmutlane and
  • Henok H. Kinfe

Beilstein J. Org. Chem. 2018, 14, 1668–1692, doi:10.3762/bjoc.14.143

Graphical Abstract
  • -introduced into the catalytic cycle. Several copper salts (CuCl, CuCl2, CuOAc and Cu(OAc)2) were evaluated as part of optimizing the reaction conditions and they all provided poor yields. 3.3.3 Acetoxysulfenylation of Baylis–Hillman alcohols. Yadav and Aswathi reported a regioselective CuI-imidazole
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Published 05 Jul 2018

Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis

  • Gwendal Grelier,
  • Benjamin Darses and
  • Philippe Dauban

Beilstein J. Org. Chem. 2018, 14, 1508–1528, doi:10.3762/bjoc.14.128

Graphical Abstract
  • 66 following the reaction of cyclic diaryl-λ3-iodanes with potassium thioacetate as the sulfur donor, and CuCl2 as the catalyst (Scheme 29) [69]. The reaction can be performed either in THF or DMSO, affording both symmetrical and non-symmetrical products in good to excellent yields. The scope of the
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Published 21 Jun 2018

Exploring mechanochemistry to turn organic bio-relevant molecules into metal-organic frameworks: a short review

  • Vânia André,
  • Sílvia Quaresma,
  • João Luís Ferreira da Silva and
  • M. Teresa Duarte

Beilstein J. Org. Chem. 2017, 13, 2416–2427, doi:10.3762/bjoc.13.239

Graphical Abstract
  • with ZnCl2 and CuCl2·2H2O by manually grinding both solids. Gabapentin is a neuroleptic drug used for the prevention of seizures, the treatment of mood disorders, anxiety, tardive dyskinesia [111][112][113][114][115][116][117][118][119], and neuropathic pain [120]. The synthesis of these coordination
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Published 14 Nov 2017

Strategies toward protecting group-free glycosylation through selective activation of the anomeric center

  • A. Michael Downey and
  • Michal Hocek

Beilstein J. Org. Chem. 2017, 13, 1239–1279, doi:10.3762/bjoc.13.123

Graphical Abstract
  • . One very powerful application of this research is the formation of α-glycosyl 1-phosphates under mild conditions with high selectivity [93]. By using simply CuCl2 as an oxidant and 2-methyl-2-oxazoline as an additive in the presence of phosphoric acid, α-glycosyl 1-phosphates could be isolated in good
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Published 27 Jun 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

Graphical Abstract
  • carried out in water, avoiding the use of an organic solvent. In addition, a broad substrate scope was observed; some sensitive functional groups, such as carboxylic acid, aldehyde and cyano were well tolerated. In 2013, the Zhou group used lithium L-prolinate (L12) as ligand and developed a CuCl2
  • aryl methyl ethers. Several examples using catalytic amounts of copper catalyst have also been reported. In 2012, the Lei group developed mild conditions using a catalytic amount of CuCl2 to convert heterocycles to the hydroxylated products in the presence of NaOt-Bu in the air at room temperature
  • (Scheme 28) [57]. Muti-halogenated arenes also gave the corresponding phenols when treated under the above mentiond conditions. An mechanistic investigation showed that NaOt-Bu was a crucial reagent which played dual roles in affording the active CuOt-Bu from CuCl2, and deprotonation of heteroarenes
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Published 23 Mar 2017

Stereo- and regioselectivity of the hetero-Diels–Alder reaction of nitroso derivatives with conjugated dienes

  • Lucie Brulíková,
  • Aidan Harrison,
  • Marvin J. Miller and
  • Jan Hlaváč

Beilstein J. Org. Chem. 2016, 12, 1949–1980, doi:10.3762/bjoc.12.184

Graphical Abstract
  • oxidation in the presence of catalytic amounts of Cu(II) and pyridine [48][49][50] were used for the preparation of acylnitroso compounds. In 2015, the Whiting group reported an extensive study of acylnitroso compounds prepared in situ by the catalytic aerobic oxidation of hydroxycarbamate using CuCl2 and 2
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Published 01 Sep 2016

Synergistic chiral iminium and palladium catalysis: Highly regio- and enantioselective [3 + 2] annulation reaction of 2-vinylcyclopropanes with enals

  • Haipan Zhu,
  • Peile Du,
  • Jianjun Li,
  • Ziyang Liao,
  • Guohua Liu,
  • Hao Li and
  • Wei Wang

Beilstein J. Org. Chem. 2016, 12, 1340–1347, doi:10.3762/bjoc.12.127

Graphical Abstract
  • amine I in CH2Cl2 at rt for 48 h (Table 1). A series of Lewis acids were initially screened. FeCl3 and Cu(OTf)2 gave the 1,2-cycloaddition product tetrahydrofuran 4a (Table 1, entries 1 and 2). It is also disappointing that others Lewis acids, such as CuCl2, MgI2, ZnBr2, ZnCl2 and FeCl2 failed to
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Published 29 Jun 2016

Copper-catalyzed [3 + 2] cycloaddition of (phenylethynyl)di-p-tolylstibane with organic azides

  • Mizuki Yamada,
  • Mio Matsumura,
  • Yuki Uchida,
  • Masatoshi Kawahata,
  • Yuki Murata,
  • Naoki Kakusawa,
  • Kentaro Yamaguchi and
  • Shuji Yasuike

Beilstein J. Org. Chem. 2016, 12, 1309–1313, doi:10.3762/bjoc.12.123

Graphical Abstract
  • alkyne, an organic azide, and an H-phosphate in the presence of CuCl2 (10 mol %) and triethylamine (2 equiv) afforded the desired 1,2,3-triazolyl-5-phosphonates [23]. Fokin et al. carried out the reaction of ethynylbismuthane with organic azides using CuOTf (5 mol %) and isolated 5-bismuthano-1,2,3
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Published 23 Jun 2016

Synthesis of 2-oxindoles via 'transition-metal-free' intramolecular dehydrogenative coupling (IDC) of sp2 C–H and sp3 C–H bonds

  • Nivesh Kumar,
  • Santanu Ghosh,
  • Subhajit Bhunia and
  • Alakesh Bisai

Beilstein J. Org. Chem. 2016, 12, 1153–1169, doi:10.3762/bjoc.12.111

Graphical Abstract
  • -oxindoles while working on asymmetric synthesis of 3,3-disubstituted-2-oxindoles via a Pd-catalyzed (chiral N-heterocyclic carbene as ligands) intramolecular α-arylation of an amide [35][36][37]. For this 'intramolecular dehydrogenative coupling' (IDC) of Csp2-H and Csp3-H they used 2.2 equiv of CuCl2 and 5
  • the oxidant. Carbocation 23c is stabilized by the amide nitrogen as shown in 23d. Eventually, in the presence of base, rearomatization of 23d takes place to afford the final product of the oxidative coupling reaction. Kündig et al. in their oxidative coupling process using 2.2 equivalent of CuCl2
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Published 08 Jun 2016

Enantioselective carbenoid insertion into C(sp3)–H bonds

  • J. V. Santiago and
  • A. H. L. Machado

Beilstein J. Org. Chem. 2016, 12, 882–902, doi:10.3762/bjoc.12.87

Graphical Abstract
  • transformation was regio and stereoselective where the main product was trans-γ-lactam (56). The chiral rhodium complexes (S)-17, (S)-18 and (S)-23 were also evaluated and yielded similar regio- and diastereoselectivity, however, with lower enantioselectivity when compared to the bis(oxazoline)/CuCl2/NaBARF
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Published 04 May 2016

Copper-mediated arylation with arylboronic acids: Facile and modular synthesis of triarylmethanes

  • H. Surya Prakash Rao and
  • A. Veera Bhadra Rao

Beilstein J. Org. Chem. 2016, 12, 496–504, doi:10.3762/bjoc.12.49

Graphical Abstract
  • ) Cu(acac)2 (36%, Table 1, entry 3), CuSO4·5H2O (36%, Table 1, entry 4), CuBr2 (14%, Table 1, entry 5), CuCl2·2H2O (24%, Table 1, entry 6) and CuO (no reaction, Table 1, entry 8), which did not provide the desired triphenylmethane (11a) in better yield. However, 20 mol % of Cu(OTf)2 (Table 1, entry 17
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Published 11 Mar 2016
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