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Search for "substitution reactions" in Full Text gives 135 result(s) in Beilstein Journal of Organic Chemistry.

Functionalization of 4-bromobenzo[c][2,7]naphthyridine via regioselective direct ring metalation. A novel approach to analogues of pyridoacridine alkaloids

  • Benedikt C. Melzer,
  • Alois Plodek and
  • Franz Bracher

Beilstein J. Org. Chem. 2019, 15, 2304–2310, doi:10.3762/bjoc.15.222

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  • 4,5-disubstituted benzo[c][2,7]naphthyridines utilizing ortho-directed ring metalation/biaryl cross-coupling strategies [9]. 4-Chlorobenzo[c][2,7]naphthyridine (9a) was conveniently converted into other 4-substituted benzo[c][2,7]naphthyridines by substitution reactions with nucleophiles (alcoholates
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Published 26 Sep 2019

Synthesis of 9-O-arylated berberines via copper-catalyzed CAr–O coupling reactions

  • Qiaoqiao Teng,
  • Xinhui Zhu,
  • Qianqian Guo,
  • Weihua Jiang,
  • Jiang Liu and
  • Qi Meng

Beilstein J. Org. Chem. 2019, 15, 1575–1580, doi:10.3762/bjoc.15.161

Graphical Abstract
  • temperature, during which 9-O-methyl cleavage occurs. The resulting berberrubine (BBRB) then acts as a good precursor to 9-O-substituted derivatives through nucleophilic substitution reactions with alkyl halides (Scheme 1). By this route, not only long-chain alkyl substituents were installed, but also more
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Published 15 Jul 2019

Synthesis of ([1,2,4]triazolo[4,3-a]pyridin-3-ylmethyl)phosphonates and their benzo derivatives via 5-exo-dig cyclization

  • Aleksandr S. Krylov,
  • Artem A. Petrosian,
  • Julia L. Piterskaya,
  • Nataly I. Svintsitskaya and
  • Albina V. Dogadina

Beilstein J. Org. Chem. 2019, 15, 1563–1568, doi:10.3762/bjoc.15.159

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  • ; Introduction Due to the high polarization of the push–pull triple bond, haloacetylenes show high reactivity in nucleophilic substitution reactions. Our systematic studies of the reactions of chloroethynylphosphonates with various nucleophilic reagents have recently revealed a new direction of this reaction
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Published 12 Jul 2019

A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: a mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

  • András György Németh,
  • György Miklós Keserű and
  • Péter Ábrányi-Balogh

Beilstein J. Org. Chem. 2019, 15, 1523–1533, doi:10.3762/bjoc.15.155

Graphical Abstract
  • as enzyme inhibitors [26] or antitumor agents [27]. These species are also used as valuable synthetic intermediates [28] and chemosensors for mercury and silver [29][30]. The general methods for the synthesis of O-thiocarbamates and dithiocarbamates traditionally rely on substitution reactions of the
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Published 10 Jul 2019

Coordination chemistry and photoswitching of dinuclear macrocyclic cadmium-, nickel-, and zinc complexes containing azobenzene carboxylato co-ligands

  • Jennifer Klose,
  • Tobias Severin,
  • Peter Hahn,
  • Alexander Jeremies,
  • Jens Bergmann,
  • Daniel Fuhrmann,
  • Jan Griebel,
  • Bernd Abel and
  • Berthold Kersting

Beilstein J. Org. Chem. 2019, 15, 840–851, doi:10.3762/bjoc.15.81

Graphical Abstract
  • cadmium complexes 1, 6 and 8, on the other hand, were prepared by substitution reactions involving the known chlorido-bridged [Ni2L(μ-Cl)]+ or [Cd2L(μ-Cl)]+ precursors and the respective azobenzene carboxylates. All complexes were isolated as ClO4− salts with yields between 76% and 91%. The perchlorate
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Published 03 Apr 2019

Synthesis and fluorescent properties of N(9)-alkylated 2-amino-6-triazolylpurines and 7-deazapurines

  • Andrejs Šišuļins,
  • Jonas Bucevičius,
  • Yu-Ting Tseng,
  • Irina Novosjolova,
  • Kaspars Traskovskis,
  • Ērika Bizdēna,
  • Huan-Tsung Chang,
  • Sigitas Tumkevičius and
  • Māris Turks

Beilstein J. Org. Chem. 2019, 15, 474–489, doi:10.3762/bjoc.15.41

Graphical Abstract
  • -triazolylpurine and 7-deazapurine derivatives is described. A new C(2)-regioselectivity in the nucleophilic aromatic substitution reactions of 9-alkylated-2,6-diazidopurines and 7-deazapurines with secondary amines has been disclosed. The obtained intermediates, 9-alkylated-2-amino-6-azido-(7-deaza)purines, were
  • derivatives as key starting materials. We have reported here for the first time that 9-alkyl-2,6-diazidopurines exhibit C(2)-selectivity in nucleophilic aromatic substitution reactions with amines. A similar selectivity was observed also for 9-alkyl-2,6-diazido-7-deazapurines. We have also demonstrated that
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Published 15 Feb 2019

Generation of 1,2-oxathiolium ions from (arysulfonyl)- and (arylsulfinyl)allenes in Brønsted acids. NMR and DFT study of these cations and their reactions

  • Stanislav V. Lozovskiy,
  • Alexander Yu. Ivanov,
  • Olesya V. Khoroshilova and
  • Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2018, 14, 2897–2906, doi:10.3762/bjoc.14.268

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  • cases, these reactions were unselective. For instance, for allene 2a, mixtures of butadiene Z-3a and alcohol Z-4a were obtained. To overcome this obstacle we decided to use 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP), which was known to form the corresponding ether for further substitution reactions [33
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Published 22 Nov 2018

An amine protecting group deprotectable under nearly neutral oxidative conditions

  • Shahien Shahsavari,
  • Chase McNamara,
  • Mark Sylvester,
  • Emily Bromley,
  • Savannah Joslin,
  • Bao-Yuan Lu and
  • Shiyue Fang

Beilstein J. Org. Chem. 2018, 14, 1750–1757, doi:10.3762/bjoc.14.149

Graphical Abstract
  • , the dM-Dmoc group is expected to be more stable under nucleophilic conditions, which will allow many transformations including base hydrolysis of esters and amides, hydride reduction of carbonyl compounds, and a wide range of nucleophilic substitution reactions to be carried out without losing the
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Published 13 Jul 2018

Rapid transformation of sulfinate salts into sulfonates promoted by a hypervalent iodine(III) reagent

  • Elsa Deruer,
  • Vincent Hamel,
  • Samuel Blais and
  • Sylvain Canesi

Beilstein J. Org. Chem. 2018, 14, 1203–1207, doi:10.3762/bjoc.14.101

Graphical Abstract
  • , decarboxylation, and fragmentation [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27]. The sulfonate group is a useful functionality frequently employed as a leaving group in substitution reactions. Production of sulfonates [28] from alcohols generally involves reaction with a
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Published 24 May 2018

Synthesis and stability of strongly acidic benzamide derivatives

  • Frederik Diness,
  • Niels J. Bjerrum and
  • Mikael Begtrup

Beilstein J. Org. Chem. 2018, 14, 523–530, doi:10.3762/bjoc.14.38

Graphical Abstract
  • trifluoromethanesulfonamide group are reported. Novel derivatives of these types of acids were synthesized in good yields. The generated N-triflylbenzamides were further functionalized through cross-coupling and nucleophilic aromatic substitution reactions. All compounds were stable in dilute aqueous solutions. Studies of
  • ) or trifluoroacetic acid (3) are not readily modified, and changing substituents on these acids will heavily impact their pKa value (Figure 1). In contrast, halogenated benzoic acid derivatives are easily functionalized through cross-coupling [4][5] or nucleophilic aromatic substitution reactions
  • Strategic Research Foundation of Energy and Environment is acknowledged for supporting this research (Grant 2104-05-0026). Lundbeck A/S is acknowledged for supporting research within nucleophilic aromatic substitution reactions.
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Published 27 Feb 2018

Stereochemical outcomes of C–F activation reactions of benzyl fluoride

  • Neil S. Keddie,
  • Pier Alexandre Champagne,
  • Justine Desroches,
  • Jean-François Paquin and
  • David O'Hagan

Beilstein J. Org. Chem. 2018, 14, 106–113, doi:10.3762/bjoc.14.6

Graphical Abstract
  • years, there has been an increasing interest in C–F bond activation [2], with a view to using organic bound fluoride as a leaving group in substitution reactions that typically require more activated leaving groups. Such an approach could circumvent the requirement for protecting groups in multistep
  • explore the stereointegrity of the aforementioned reactions using enantiopure 7-[2H1]-(R)-benzyl fluoride ((R)-1, Figure 2) as a primary, yet chiral electrophile [10]. Substitution reactions of benzyl fluoride (1) will generate substituted products that retain the deuterium atom, and the degree of
  • reactions using a mixture of nucleophiles (for direct substitutions) and aryls (for Friedel–Crafts reactions) to give products 5–9. The nucleophilic substitution reactions of 1 are shown in Table 1 and Table 2, and were all conducted using either a mixture of water/isopropanol, or tris(hydroxymethyl)propane
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Published 09 Jan 2018

Photocatalytic formation of carbon–sulfur bonds

  • Alexander Wimmer and
  • Burkhard König

Beilstein J. Org. Chem. 2018, 14, 54–83, doi:10.3762/bjoc.14.4

Graphical Abstract
  • –S bonds were developed and already excellently reviewed, including nucleophilic substitution reactions between S-nucleophiles and organic electrophiles, metal-catalyzed C–S bond formations and organocatalytic or enzymatic approaches [15][16][18][20][21][22]. This review provides a brief overview
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Published 05 Jan 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

Binding abilities of polyaminocyclodextrins: polarimetric investigations and biological assays

  • Marco Russo,
  • Daniele La Corte,
  • Annalisa Pisciotta,
  • Serena Riela,
  • Rosa Alduina and
  • Paolo Lo Meo

Beilstein J. Org. Chem. 2017, 13, 2751–2763, doi:10.3762/bjoc.13.271

Graphical Abstract
  • a different number of polyamine branches linked to the CD scaffold, that are isolated as partial hydrohalides. In fact, the same polyamine unit can undergo multiple substitution reactions (a possible mechanistic scheme is depicted in Supporting Information File 1, Figure S1), on the same N atom or
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Published 18 Dec 2017

Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

  • Satoru Mori and
  • Norio Shibata

Beilstein J. Org. Chem. 2017, 13, 2273–2296, doi:10.3762/bjoc.13.224

Graphical Abstract
  • conditions (Scheme 10) [129]. There are two methods to synthesize subphthalocyanine derivatives, mainly peripheral functionalization and substitution of axial positions. Among them, substitution reactions at the axial position can easily deliver many subphthalocyanine derivatives by coordinating various
  • chemical species with one subphthalocyanine as a foothold. However, it is known that axial substitution reactions proceed with low yield with ordinary subphthalocyanine [130]. On the other hand, TFEO-subPc remarkably improves the substitution activity at its axial position, and the axial substitution
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Published 27 Oct 2017

The effect of milling frequency on a mechanochemical organic reaction monitored by in situ Raman spectroscopy

  • Patrick A. Julien,
  • Ivani Malvestiti and
  • Tomislav Friščić

Beilstein J. Org. Chem. 2017, 13, 2160–2168, doi:10.3762/bjoc.13.216

Graphical Abstract
  • situ XRPD monitoring of the formation of glycinium oxalate salts from γ-glycine and oxalic acid dihydrate [42]. Other examples of explorations of the effect of milling frequency on mechanochemical reactivity include aromatic substitution reactions [43] and the synthesis of nitrogen-doped titania [44
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Published 18 Oct 2017

Preparation of imidazo[1,2-a]-N-heterocyclic derivatives with gem-difluorinated side chains

  • Layal Hariss,
  • Kamal Bou Hadir,
  • Mirvat El-Masri,
  • Thierry Roisnel,
  • René Grée and
  • Ali Hachem

Beilstein J. Org. Chem. 2017, 13, 2115–2121, doi:10.3762/bjoc.13.208

Graphical Abstract
  • , respectively. On the other hand, two nucleophilic substitution reactions using phenol and morpholine gave the expected heterocycles 10 and 11 in 73% and 23% yields, respectively. Conclusion In summary, we developed a short and completely regioselective method for the synthesis of imidazo[1,2-a]-N-heterocycles
  • . Coupling and substitution reactions. Supporting Information Supporting Information File 310: Experimental details and characterization data of new compounds with copies of 1H, 13C and 19F NMR spectra. Acknowledgements This work was financially supported by the Research Grant Program at Lebanese
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Published 10 Oct 2017

Main group mechanochemistry

  • Agota A. Gečiauskaitė and
  • Felipe García

Beilstein J. Org. Chem. 2017, 13, 2068–2077, doi:10.3762/bjoc.13.204

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  • ) (Cp′ = C5Me4(n-Pr)). Mechanochemical synthesis of the Ar-BIAN ligands and indium(III) complexes (top). One-pot synthesis of an indium complex (bottom). Synthesis of germanes from germanium (Ge) or germanium oxide (GeO2). Ball-milling nucleophilic substitution reactions to produce acyclic and cyclic
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Published 05 Oct 2017

Mechanochemical synthesis of small organic molecules

  • Tapas Kumar Achar,
  • Anima Bose and
  • Prasenjit Mal

Beilstein J. Org. Chem. 2017, 13, 1907–1931, doi:10.3762/bjoc.13.186

Graphical Abstract
  • Coville and co-workers presented solvent-free organometallic transformations (e.g., migratory insertion and ligand substitution reactions) at elevated temperature (Scheme 44) which have close resemblance to mechanochemistry [173]. The examples of mechanochemical organometallic complex synthesis are
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Published 11 Sep 2017

Influence of the milling parameters on the nucleophilic substitution reaction of activated β-cyclodextrins

  • László Jicsinszky,
  • Kata Tuza,
  • Giancarlo Cravotto,
  • Andrea Porcheddu,
  • Francesco Delogu and
  • Evelina Colacino

Beilstein J. Org. Chem. 2017, 13, 1893–1899, doi:10.3762/bjoc.13.184

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  • . The reaction was performed in a planetary ball mill and the processing parameters were systematically varied with the aim of pointing out their influence on the nucleophilic substitution reactions in terms of rate and yield. Specifically systematic variation involved rotation speed, milling tool
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Published 07 Sep 2017

α-Acetoxyarone synthesis via iodine-catalyzed and tert-butyl hydroperoxide-mediateded self-intermolecular oxidative coupling of aryl ketones

  • Liquan Tan,
  • Cui Chen and
  • Weibing Liu

Beilstein J. Org. Chem. 2017, 13, 1079–1084, doi:10.3762/bjoc.13.107

Graphical Abstract
  • products and pharmaceuticals, and α-acetoxyaryl ketones are widely used as synthetic intermediates [1][2][3][4][5]. Traditional methods for the preparation of α-acyloxy ketones focus on the substitution reactions of α-halo carbonyl compounds with alkaline carboxylates or carboxylic acids [6][7], and
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Published 06 Jun 2017

Metal-free hydroarylation of the side chain carbon–carbon double bond of 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles in triflic acid

  • Anna S. Zalivatskaya,
  • Dmitry S. Ryabukhin,
  • Marina V. Tarasenko,
  • Alexander Yu. Ivanov,
  • Irina A. Boyarskaya,
  • Elena V. Grinenko,
  • Ludmila V. Osetrova,
  • Eugeniy R. Kofanov and
  • Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2017, 13, 883–894, doi:10.3762/bjoc.13.89

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  • xylenes, mesitylene, pseudocumene, or durene gave mixtures of oligomeric products. Probably, these products are formed through multiple electrophilic substitution reactions of these arenes by the reactive dication species D. When oxadiazole 1b reacted with tert-butylbenzene (Table 2, entry 10), product 2f
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Published 11 May 2017

Fluorinated cyclohexanes: Synthesis of amine building blocks of the all-cis 2,3,5,6-tetrafluorocyclohexylamine motif

  • Tetiana Bykova,
  • Nawaf Al-Maharik,
  • Alexandra M. Z. Slawin and
  • David O'Hagan

Beilstein J. Org. Chem. 2017, 13, 728–733, doi:10.3762/bjoc.13.72

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  • motif by the wider research community requires that a range of building blocks be prepared. It has proven relatively straightforward to prepare the phenyl derivative 2 and then subsequent elaboration to a range of functionalized analogues by standard electrophilic aromatic substitution reactions (Figure
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Published 19 Apr 2017

Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill

  • Olga Eguaogie,
  • Patrick F. Conlon,
  • Francesco Ravalico,
  • Jamie S. T. Sweet,
  • Thomas B. Elder,
  • Louis P. Conway,
  • Marc E. Lennon,
  • David R. W. Hodgson and
  • Joseph S. Vyle

Beilstein J. Org. Chem. 2017, 13, 87–92, doi:10.3762/bjoc.13.11

Graphical Abstract
  • liquid [13][14][15]. Recently, Jicsinszky et al. described using a planetary ball mill to perform substitution reactions of 6I-O-(p-toluenesulfonyl)-β-cyclodextrin (Ts-β-CD) with azide, halide or thiolate nucleophiles and thereby avoided intramolecular cyclisation (commonly found under solution-phase
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Published 13 Jan 2017

Experimental and theoretical investigations into the stability of cyclic aminals

  • Edgar Sawatzky,
  • Antonios Drakopoulos,
  • Martin Rölz,
  • Christoph Sotriffer,
  • Bernd Engels and
  • Michael Decker

Beilstein J. Org. Chem. 2016, 12, 2280–2292, doi:10.3762/bjoc.12.221

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  • the strong non-nucleophilic base t-BuOK to give compound 12a. The target compound 13a could then be obtained by reduction of 12 with LiAlH4. As the substitution reactions using 11 failed with iPrI, a second synthetic pathway was pursued to alter the substituents at the N-1 nitrogen atom of the
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Published 31 Oct 2016
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