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Search for "alkynes" in Full Text gives 497 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

A novel and robust heterogeneous Cu catalyst using modified lignosulfonate as support for the synthesis of nitrogen-containing heterocycles

  • Bingbing Lai,
  • Meng Ye,
  • Ping Liu,
  • Minghao Li,
  • Rongxian Bai and
  • Yanlong Gu

Beilstein J. Org. Chem. 2020, 16, 2888–2902, doi:10.3762/bjoc.16.238

Graphical Abstract
  • -Cu-promoted conditions as well, and gave the product 4o in 65% yield. The successful attempts in the three-component reaction of 4-aminoindoles (1a), alkynes and aldehydes indicate that the heterogeneous catalyst LS-FAS-Cu is competent for catalyzing nitrogen-containing heterocyclic compounds without
  • ). Recyclability of LS-FAS-Cu, LS-FM-Cu and Resin-Cu in the reaction between compounds 1a, 2a and 3a. Substrate scope of LS-FAS-Cu catalyzed three-component reactions of 4-aminoindoles, alkynes and aldehydes. Three-component reaction of 1a, 2a, and 3a to synthesis of 4aa. Optimizing the reaction condition of
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Published 26 Nov 2020

Synthesis and investigation of quadruplex-DNA-binding, 9-O-substituted berberine derivatives

  • Jonas Becher,
  • Daria V. Berdnikova,
  • Heiko Ihmels and
  • Christopher Stremmel

Beilstein J. Org. Chem. 2020, 16, 2795–2806, doi:10.3762/bjoc.16.230

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  • -forming repeat unit from the “insulin-linked polymorphic region” (ILPR) [50], that was also shown to bind quadruplex ligands [51]. Results Synthesis As the Cu-catalyzed click reaction between azides and alkynes is a well-established method for the variable functionalization of G4-DNA ligands [52], the
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Published 18 Nov 2020

Easy access to a carbohydrate-based template for stimuli-responsive surfactants

  • Thomas Holmstrøm,
  • Daniel Raydan and
  • Christian Marcus Pedersen

Beilstein J. Org. Chem. 2020, 16, 2788–2794, doi:10.3762/bjoc.16.229

Graphical Abstract
  • ]. Furthermore, starting from the azide 8, it was possible to achieve ester functionalities by a CuAAC reaction [23][24] in the presence of the two different alkynes 14 and 15, giving rise to the diester derivative 12 and the tetraester derivative 13 (Scheme 2). Subsequently, the esters could be hydrolyzed by
  • functionalization. The azido groups also can undergo a CuAAC reaction with alkynes substituted with ester functionalities, which can subsequently be hydrolyzed to either the di- or tetra acids. Using the CuAAC reaction, it was also possible to install aliphatic chains. Introducing picoline residues on the 3,6
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Published 17 Nov 2020

Ring-closing metathesis of prochiral oxaenediynes to racemic 4-alkenyl-2-alkynyl-3,6-dihydro-2H-pyrans

  • Viola Kolaříková,
  • Markéta Rybáčková,
  • Martin Svoboda and
  • Jaroslav Kvíčala

Beilstein J. Org. Chem. 2020, 16, 2757–2768, doi:10.3762/bjoc.16.226

Graphical Abstract
  • intermediate to undergo subsequent metathesis reactions leading to catalyst deactivation [23]. In both cases, the effect of ethene was especially productive for the Grubbs 1st generation precatalyst and is typically applied for terminal alkynes or alkynes with little steric hindrance of the triple bond. In
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Published 13 Nov 2020

Selective and reversible 1,3-dipolar cycloaddition of 6-aryl-1,5-diazabicyclo[3.1.0]hexanes with 1,3-diphenylprop-2-en-1-ones under microwave irradiation

  • Alexander P. Molchanov,
  • Mariia M. Efremova,
  • Mariya A. Kryukova and
  • Mikhail A. Kuznetsov

Beilstein J. Org. Chem. 2020, 16, 2679–2686, doi:10.3762/bjoc.16.218

Graphical Abstract
  • ]. A wide range of pharmaceuticals, agrochemicals, and other biologically active compounds are prepared using different types of (3 + n) cycloadditions, mainly with alkenes and alkynes [3][4][5][6][7]. For example, N,N'-cyclic azomethine imines are precursors of biologically active bicyclic
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Published 30 Oct 2020

Recent developments in enantioselective photocatalysis

  • Callum Prentice,
  • James Morrisson,
  • Andrew D. Smith and
  • Eli Zysman-Colman

Beilstein J. Org. Chem. 2020, 16, 2363–2441, doi:10.3762/bjoc.16.197

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Published 29 Sep 2020

Design and synthesis of a bis-macrocyclic host and guests as building blocks for small molecular knots

  • Elizabeth A. Margolis,
  • Rebecca J. Keyes,
  • Stephen D. Lockey IV and
  • Edward E. Fenlon

Beilstein J. Org. Chem. 2020, 16, 2314–2321, doi:10.3762/bjoc.16.192

Graphical Abstract
  • . Keywords: alkynes; azides; host–guest; macrocycles; molecular knots; Introduction Macrocycles have played a central role in the development of molecular recognition, self-assembled molecular devices, and molecular topology [1][2][3][4][5][6]. For example, early work by Pedersen on crown ethers [1], Lehn
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Published 18 Sep 2020

Regioselective cobalt(II)-catalyzed [2 + 3] cycloaddition reaction of fluoroalkylated alkynes with 2-formylphenylboronic acids: easy access to 2-fluoroalkylated indenols

  • Tatsuya Kumon,
  • Miroku Shimada,
  • Jianyan Wu,
  • Shigeyuki Yamada and
  • Tsutomu Konno

Beilstein J. Org. Chem. 2020, 16, 2193–2200, doi:10.3762/bjoc.16.184

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  • Tatsuya Kumon Miroku Shimada Jianyan Wu Shigeyuki Yamada Tsutomu Konno Faculty of Molecular Chemistry and Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan 10.3762/bjoc.16.184 Abstract [2 + 3] cycloaddition reactions of fluorinated alkynes with 2
  • best of our knowledge, there are no reports on the practical synthesis of disubstituted 2-fluoroalkylated indenols so far. Transition-metal-catalyzed carbocyclization reactions of alkynes with benzene derivatives having a leaving group X (X = Br, I, OTs, B(OH)2) have been widely considered as one of
  • the most efficient and convenient protocols for the construction of various 2,3-disubstituted indene derivatives, such as indenols and indenamines (Scheme 1b) [23][24][25]. There have been numerous studies on the reaction with nonfluorinated alkynes under the influence of various transition metals
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Published 04 Sep 2020

Efficient [(NHC)Au(NTf2)]-catalyzed hydrohydrazidation of terminal and internal alkynes

  • Maximillian Heidrich and
  • Herbert Plenio

Beilstein J. Org. Chem. 2020, 16, 2080–2086, doi:10.3762/bjoc.16.175

Graphical Abstract
  • alkynes (7a–j, 10 examples, 0.2–0.5 mol % [(NHC)Au(NTf2)], T = 60–80 °C) utilizing a complex with a sterically demanding bispentiptycenyl-substituted NHC ligand and the benign reaction solvent anisole, is reported. Keywords: alkyne; gold; homogeneous catalysis; hydrohydrazidation; NHC ligand
  • ; Introduction Cationic gold complexes with weakly coordinating counterions (which are often considered to be solvent-separated ions) [1][2][3], render powerful catalysts for the transformation of organic substrates [4][5][6], specifically the reactions of alkynes with a variety of heteroatom nucleophiles
  • % at 60 °C were required to obtain the respective addition product in yields of 66–93%. Internal alkynes were much less reactive and even at 12 mol % catalyst loading the reaction of 3-hexyne and PhCONHNH2 yielded the respective addition product in only 32% yield, with diphenylacetylene only 12% of the
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Published 26 Aug 2020

Reactions of 3-aryl-1-(trifluoromethyl)prop-2-yn-1-iminium salts with 1,3-dienes and styrenes

  • Thomas Schneider,
  • Michael Keim,
  • Bianca Seitz and
  • Gerhard Maas

Beilstein J. Org. Chem. 2020, 16, 2064–2072, doi:10.3762/bjoc.16.173

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  • cyclobutene and several cationic intermediates and mainly yield 2-(1-phenylvinyl)indenes. In a similar reaction cascade, a fulvene derivative was obtained with 1,4-diphenylbutadiene as the substrate. Keywords: alkynes; aromatic substitution; cyclization; cycloaddition; iminium salts; Introduction In recent
  • presumably renders an ionic [2 + 2] cycloaddition pathway competitive with the Diels–Alder reaction. The few reported examples of cyclobutene formation from alkynes and unactivated 1,3-dienes include the sensitized photocycloaddition of phenylacetylene and DMBD [30] and the gold(I)-catalyzed reaction of
  • concerted conrotatory process [47][48] would create a strained cis,trans-dihydrobenzo[8]annulene ring system. Cyclobutenes resulting from a [2 + 2] cycloaddition of electrophilic alkynes and alkenes under moderate thermal conditions have been isolated also from the reaction of CF3-free propyniminium salts
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Published 24 Aug 2020

When metal-catalyzed C–H functionalization meets visible-light photocatalysis

  • Lucas Guillemard and
  • Joanna Wencel-Delord

Beilstein J. Org. Chem. 2020, 16, 1754–1804, doi:10.3762/bjoc.16.147

Graphical Abstract
  • photocatalyst. The strategy was utilized for the C–H bond annulation of benzamides with alkynes, furnishing isoquinolones, an important moiety in various natural products (Figure 15) [78]. The C–H activation step was assisted by an 8-quinolyl DG and occurred under an oxygen atmosphere at room temperature. A
  • , pyrimidyl, and 7-azaindolyl were found to be compatible with this transformation. While symmetrical alkynes led to the desired products in moderate to good yields, the unsymmetrical ones afforded a mixture of products with very high regioselectivity, with the favored formation of cyclized compounds bearing
  • performed under air at high temperatures. The coupling exhibited a broad substrate scope and the procedure tolerated a variety of even sensitive functional groups, including trifluoromethyl, ketone, or ester motifs. Unsymmetrical alkynes were also compatible, although the cyclization provided the desired
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Published 21 Jul 2020

Clickable azide-functionalized bromoarylaldehydes – synthesis and photophysical characterization

  • Dominik Göbel,
  • Marius Friedrich,
  • Enno Lork and
  • Boris J. Nachtsheim

Beilstein J. Org. Chem. 2020, 16, 1683–1692, doi:10.3762/bjoc.16.139

Graphical Abstract
  • cycloadditions with model alkynes. Besides two ortho- and para-bromo-substituted benzaldehydes, the azide functionalization of a fluorene-based structure will be presented. The copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) of the so-synthesized azide-functionalized bromocarbaldehydes with terminal
  • alkynes, exhibiting different degrees of steric demand, was performed in high efficiency. Finally, we investigated the photophysical properties of the azide-functionalized arenes and their covalently linked triazole derivatives to gain deeper insight towards the effect of these covalent linkers on the
  • reactions (CuAAC). For this, we treated the azide-functionalized luminophores with alkynes exhibiting different degrees of steric demand, including 1-decyne (29), phenylacetylene (30), 1-ethynyladamantane (31) and 1,3-di-tert-butyl-5-ethynylbenzene (32, see Scheme 5). All triazoles 33–44, based on the
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Published 14 Jul 2020

Pauson–Khand reaction of fluorinated compounds

  • Jorge Escorihuela,
  • Daniel M. Sedgwick,
  • Alberto Llobat,
  • Mercedes Medio-Simón,
  • Pablo Barrio and
  • Santos Fustero

Beilstein J. Org. Chem. 2020, 16, 1662–1682, doi:10.3762/bjoc.16.138

Graphical Abstract
  • that will be discussed in this review belongs to the fluorinated building blocks category. More specifically, the participation of fluorine-containing olefins and alkynes in the Pauson–Khand cyclization, with a special focus on the intramolecular version using fluorinated enynes, which will be
  • the intramolecular version, the fluorine atom or fluorinated group can also form a part of the linker. The reaction yields are dependent on the degree of substitution, bulkiness, and electronic effects of the substituents of both the alkyne and alkene moieties. In general, electron-deficient alkynes
  • are poor substrates for the PKR as they are deactivated in the cobalt-complexation step, and the highest yields are usually obtained with terminal alkynes. The scenario is similar in the case of fluorinated substrates, with the intramolecular version being much more developed than the intermolecular
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Published 14 Jul 2020

Fluorohydration of alkynes via I(I)/I(III) catalysis

  • Jessica Neufeld,
  • Constantin G. Daniliuc and
  • Ryan Gilmour

Beilstein J. Org. Chem. 2020, 16, 1627–1635, doi:10.3762/bjoc.16.135

Graphical Abstract
  • -molecule catalysis. Herein, we disclose an intriguing example of substrate specificity that was observed whilst exploring catalysis-based routes to generate α-fluoroketones from terminal and internal alkynes under the auspices of I(I)/I(III) catalysis. Utilising p-TolI as an inexpensive organocatalyst with
  • Selectfluor® and amine/HF mixtures, the formation of protected α-fluoroketones from simple alkynes was realised. Whilst the transient p-TolIF2 species generated in situ productively engaged with pentynyl benzoate scaffolds to generate the desired α-fluoroketone motif, augmentation or contraction of the linker
  • fluorination of acetophenone derivatives was achieved using iodosylarenes and commercially available NEt3/HF 1:5 to generate the ArIF2 species in situ is also highly pertinent [39][40] (Figure 1A). Elegant reports describing the conversion of internal alkynes to α-fluoroketones via π-acid catalysis were also
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Published 10 Jul 2020

Azidophosphonium salt-directed chemoselective synthesis of (E)/(Z)-cinnamyl-1H-triazoles and regiospecific access to bromomethylcoumarins from Morita–Baylis–Hillman adducts

  • Soundararajan Karthikeyan,
  • Radha Krishnan Shobana,
  • Kamarajapurathu Raju Subimol,
  • J. Helen Ratna Monica and
  • Ayyanoth Karthik Krishna Kumar

Beilstein J. Org. Chem. 2020, 16, 1579–1587, doi:10.3762/bjoc.16.130

Graphical Abstract
  • for the synthesis of 3-(bromomethyl)coumarins. Literature-reported cycloaddition reactions of MBH acetates involving azides and alkynes [24][25][26][27][28]. Synthetic methodologies for triazolations of MBH adducts. a) Literature-reported indirect triazolation of MBH adducts [32][33]. b) This work
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Published 01 Jul 2020

Photocatalyzed syntheses of phenanthrenes and their aza-analogues. A review

  • Alessandra Del Tito,
  • Havall Othman Abdulla,
  • Davide Ravelli,
  • Stefano Protti and
  • Maurizio Fagnoni

Beilstein J. Org. Chem. 2020, 16, 1476–1488, doi:10.3762/bjoc.16.123

Graphical Abstract
  • occurring on a stilbene diazonium salt (e.g., 1.1+) with the intermediacy of an aryl radical [40]. Alternative strategies for the synthesis of phenanthrenes have been later reported, including the adoption of [4 + 2] benzannulations between biaryl derivatives and alkynes [41][42]. Scheme 2 illustrates one
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Published 25 Jun 2020

An overview on disulfide-catalyzed and -cocatalyzed photoreactions

  • Yeersen Patehebieke

Beilstein J. Org. Chem. 2020, 16, 1418–1435, doi:10.3762/bjoc.16.118

Graphical Abstract
  • used similar disulfide-catalyzed [3 + 2] cycloaddition reactions for the synthesis of polycyclic frameworks. The irradiation of vinylcyclopropanes with alkenes or alkynes in the presence of dibutyl disulfide afford the desired bi- or tricyclic products with 54–88% yield (Scheme 2) [6]. In 2014, Maruoka
  • also catalyze the formation of four-membered ring intermediates between double or triple bonds and oxygen, and thus converting unsaturated hydrocarbons to carbonyl compounds. Regarding the oxidation of alkynes, Wang reported a method for preparing diaryl-1,2-diketones from diarylalkynes in the presence
  • groups that contain heteroatoms. Ogawa and co-workers reported a class of efficient diboration reactions. Under light irradiation, disulfide was used as the photocatalyst to facilitate the addition of bis(pinacolato)diboron (B2pin2) to terminal alkynes [19], and the corresponding diboryl alkenes were
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Published 23 Jun 2020

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

  • Stephanie G. E. Amos,
  • Marion Garreau,
  • Luca Buzzetti and
  • Jerome Waser

Beilstein J. Org. Chem. 2020, 16, 1163–1187, doi:10.3762/bjoc.16.103

Graphical Abstract
  • alkynes. They can also perform atom abstractions, in particular HATs and halogen abstractions [66]. The generation of such species generally occurs through the homolytic cleavage of a peripheral σ bond [67][68]. In the majority of the cases, a leaving group is reduced and fragments to the aryl radical
  • class of substrates that usually undergo a protonation to form C(sp3) radicals. Alkenyl or aryl radical ions are generally accessed through SET. The presence of electron-donating groups facilitates the oxidation of the precursor to the radical cations, while electron-poor alkynes and arenes can undergo
  • reaction (Scheme 23) [100]. The alkynes 23.1 could be successfully converted to the vinyl sulfones 23.3 in the presence of the aryl sulfones 23.2 using eosin Y (OD13) as a photocatalyst. A tentative mechanism was proposed by the authors: under visible-light irradiation, the arylsulfinic acid could be
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Published 29 May 2020

Palladium-catalyzed regio- and stereoselective synthesis of aryl and 3-indolyl-substituted 4-methylene-3,4-dihydroisoquinolin-1(2H)-ones

  • Valeria Nori,
  • Antonio Arcadi,
  • Armando Carlone,
  • Fabio Marinelli and
  • Marco Chiarini

Beilstein J. Org. Chem. 2020, 16, 1084–1091, doi:10.3762/bjoc.16.95

Graphical Abstract
  • antimetastatic agents [14]. Fittingly, the development of efficient strategies for their construction and peripheral functionalization represents still an active research area aimed to achieve structural diversity [15][16][17][18]. Carbometalations of alkynes constitute a powerful tool for the regio- and
  • functionalized alkynes with boronic acids [32][33] prompted us to explore the palladium-catalyzed reaction of the readily available alkynyliodobenzamides 2 with boronic acids 3 as a viable route to the regio- and stereoselective synthesis of 4-alkylidene-3,4-dihydroisoquinolin-1(2H)-ones 3 (Scheme 1a). We are
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Published 20 May 2020

Copper-based fluorinated reagents for the synthesis of CF2R-containing molecules (R ≠ F)

  • Louise Ruyet and
  • Tatiana Besset

Beilstein J. Org. Chem. 2020, 16, 1051–1065, doi:10.3762/bjoc.16.92

Graphical Abstract
  • functionalization of alkyl bromides, alkyl mesylates, aryldiazonium salts [43] as well as electron-rich arenes [44] (Scheme 4). In 2015, the group of Qing investigated the oxidative difluoromethylation reaction of terminal alkynes with TMSCF2H via a copper-mediated reaction [45]. Using a stoichiometric amount of
  • CuI, in the presence of t-BuOK and 9,10-phenanthraquinone, the functionalization of a panel of (hetero)aromatic and aliphatic terminal alkynes was achieved (Scheme 5). A good functional group tolerance was observed as alkynes bearing a cyano, ester, bromo or amino group among others were suitable
  • substrates. Based on 19F NMR studies, the authors suggested the following mechanism: first the in situ generation of a CuCF2H complex from TMSCF2H in equilibrium with the corresponding cuprate (Cu(CF2H)2−) occurred followed by the reaction with terminal alkynes under basic conditions. The resulting
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Published 18 May 2020

Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches

  • Rodrigo Costa e Silva,
  • Luely Oliveira da Silva,
  • Aloisio de Andrade Bartolomeu,
  • Timothy John Brocksom and
  • Kleber Thiago de Oliveira

Beilstein J. Org. Chem. 2020, 16, 917–955, doi:10.3762/bjoc.16.83

Graphical Abstract
  • ). For an oxidative quenching, the photoarylation of heteroarenes and alkynes with aryldiazonium salts, and the oxidative decarboxylative coupling between cinnamic acid and tetrahydrofuran also showed better results when NiTPP was used instead of eosin [32][33][34] (Scheme 10). Regarding protocols
  • hydration of terminal alkynes to ketones can be photocatalyzed by rhodium(III) tetrakis(p-sulfonylphenyl)porphyrin (RhIIITSPP) [37]. The coupling between RhIII(TSPP) and terminal alkynes produced the β-carbonylalkylrhodium porphyrin as a photoactive intermediate, whose irradiation produced the PhCOCH2
  • tetrahydroquinolines by reductive quenching. Selenylation and thiolation of anilines. NiTPP as photoredox catalyst in oxidative and reductive quenching, in comparison with other photocatalysts. C–O bond cleavage of 1-phenylethanol using a cobalt porphyrin (CoTMPP) under visible light. Hydration of terminal alkynes by
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Published 06 May 2020

Copper catalysis with redox-active ligands

  • Agnideep Das,
  • Yufeng Ren,
  • Cheriehan Hessin and
  • Marine Desage-El Murr

Beilstein J. Org. Chem. 2020, 16, 858–870, doi:10.3762/bjoc.16.77

Graphical Abstract
  • wide variety of substrates including silyl enol ethers, heteroaromatics and alkynes using an electrophilic CF3+ source (8 or 9), opening new opportunities to access pharmaceutically relevant trifluoromethylated products under mild reaction conditions. The ligand-based SET step involved the
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Published 24 Apr 2020

Recent advances in Cu-catalyzed C(sp3)–Si and C(sp3)–B bond formation

  • Balaram S. Takale,
  • Ruchita R. Thakore,
  • Elham Etemadi-Davan and
  • Bruce H. Lipshutz

Beilstein J. Org. Chem. 2020, 16, 691–737, doi:10.3762/bjoc.16.67

Graphical Abstract
  • decade later, Molander et al. made use of the same disilane as a source of the nucleophile for additions to α,β-unsaturated alkenes and alkynes as Michael acceptors bearing sulfones, nitriles, cyano, amido, and carboxyl ester groups to form β-silylated alkanes and alkenes in good to moderate yields [55
  • , could be intercepted at the intermediate radical stage (149) with radical initiator TBHP present in excess, leading to silylated peroxy products 151–156. This approach was applied to different types of conjugated systems, including esters, ketones, amides, alkynes, etc. (Scheme 27). Kleeberg [64] et al
  • bond formation Organoboron compounds are widely used in C–C and C–X (X = N, O) bond constructions. Straightforward methods for their synthesis involve the copper-catalyzed addition of organoboron compounds to alkynes, alkenes, and unsaturated carbonyl compounds, as well as the nucleophilic borylation
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Published 15 Apr 2020

Cascade trifluoromethylthiolation and cyclization of N-[(3-aryl)propioloyl]indoles

  • Ming-Xi Bi,
  • Shuai Liu,
  • Yangen Huang,
  • Xiu-Hua Xu and
  • Feng-Ling Qing

Beilstein J. Org. Chem. 2020, 16, 657–662, doi:10.3762/bjoc.16.62

Graphical Abstract
  • the direct incorporation of the SCF3 group into organic compounds [9][10][11][12][13][14][15][16], such as alkynes, alkenes, arenes, and alkanes. Despite these impressive advances, there is a continued strong demand for new methods that enable the efficient synthesis of SCF3-containing compounds
  • strategy in the synthesis of a series of CH2SCF3-substituted heterocycles. For the construction of SCF3-substituted cyclic compounds, normally proper alkynes are chosen as the substrates for cascade reactions [28][29][30][31][32]. In 2015, Wang developed an oxidative radical cyclization of aryl alkynoate
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Published 08 Apr 2020

Copper-catalyzed O-alkenylation of phosphonates

  • Nuria Vázquez-Galiñanes,
  • Mariña Andón-Rodríguez,
  • Patricia Gómez-Roibás and
  • Martín Fañanás-Mastral

Beilstein J. Org. Chem. 2020, 16, 611–615, doi:10.3762/bjoc.16.56

Graphical Abstract
  • counterparts has received less attention. Current methodologies for the synthesis of acyclic mixed enol phosphonates include the Perkow-type reaction between phosphonites and α-halocarbonyl compounds [11], the mercury-catalyzed addition of phosphonic acid monoesters to terminal alkynes [12][13] and multistep
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Published 03 Apr 2020
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