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Search for "diaryliodonium salts" in Full Text gives 37 result(s) in Beilstein Journal of Organic Chemistry.

A survey of chiral hypervalent iodine reagents in asymmetric synthesis

  • Soumen Ghosh,
  • Suman Pradhan and
  • Indranil Chatterjee

Beilstein J. Org. Chem. 2018, 14, 1244–1262, doi:10.3762/bjoc.14.107

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  • for carbonyl α-functionalizations are still considered as highly demandable in synthetic organic chemistry. In this regard transition metals have been successfully applied and even allow accomplishing such transformations asymmetrically. On the other hand, diaryliodonium salts are known to transfer
  • reactive organostannane derived Sn–I(III) exchange in the presence of BF3·Et2O was the crucial step in the synthesis of the chiral iodonium salts from 88. In view of developing asymmetric α-arylations of carbonyls, Olofsson et al. has independently synthesized a new class of diaryliodonium salts 14 with
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Published 30 May 2018

Imide arylation with aryl(TMP)iodonium tosylates

  • Souradeep Basu,
  • Alexander H. Sandtorv and
  • David R. Stuart

Beilstein J. Org. Chem. 2018, 14, 1034–1038, doi:10.3762/bjoc.14.90

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  • , transition metals feature prominently in such methods, but even recent examples employ stoichiometric metal mediators [4]. Metal-free methods by classic SNAr are also attractive, but only possible on very electron-deficient arene substrates [5]. Diaryliodonium salts are useful reagents for metal-free aryl
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Published 11 May 2018

One-pot synthesis of diaryliodonium salts from arenes and aryl iodides with Oxone–sulfuric acid

  • Natalia Soldatova,
  • Pavel Postnikov,
  • Olga Kukurina,
  • Viktor V. Zhdankin,
  • Akira Yoshimura,
  • Thomas Wirth and
  • Mekhman S. Yusubov

Beilstein J. Org. Chem. 2018, 14, 849–855, doi:10.3762/bjoc.14.70

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  • , Park Place, Main Building, Cardiff CF10 3AT, UK 10.3762/bjoc.14.70 Abstract A facile synthesis of diaryliodonium salts utilizing Oxone as versatile and cheap oxidant has been developed. This method shows wide applicability and can be used for the preparation of iodonium salts containing electron
  • -donating or electron-withdrawing groups in good yields. In addition, this procedure can be applied to the preparation of symmetric iodonium salts directly from arenes via a one-pot iodination–oxidation sequence. Keywords: diaryliodonium salts; iodine; iodonium; oxidation; Oxone; Introduction
  • Diaryliodonium salts, which are also known as diaryl-λ3-iodanes, are widely considered to be an important and practically useful class of hypervalent iodine compounds [1][2][3][4]. Diaryliodonium salts have found broad synthetic application as electrophilic arylating reagents in reactions with various
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Published 12 Apr 2018

Synthesis of fluoro-functionalized diaryl-λ3-iodonium salts and their cytotoxicity against human lymphoma U937 cells

  • Prajwalita Das,
  • Etsuko Tokunaga,
  • Hidehiko Akiyama,
  • Hiroki Doi,
  • Norimichi Saito and
  • Norio Shibata

Beilstein J. Org. Chem. 2018, 14, 364–372, doi:10.3762/bjoc.14.24

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  • the potential bioactivity of fluorine, an investigation was conducted using various fluorine-containing diaryliodonium salts in order to study and compare their biological activity against human lymphoma U937 cells. Most of the compounds tested are well-known reagents for fluoro-functionalized
  • . These results led us to synthesize more compounds, previously unknown sterically demanding diaryliodonium salts having a pentafluorosulfanyl (SF5) functional group at the ortho-position, that is, unsymmetrical ortho-SF5 phenylaryl-λ3-iodonium salts. Newly synthesized mesityl(2-(pentafluoro-λ6-sulfanyl
  • only fragmented reports on the biological activity of diaryliodonium salts [44][45][46][47][48][49]. Goldstein et al. [45] and Doroshow et al. [46] reported that some diaryliodonium salts show effective antimicrobial and NOX inhibitor activity, respectively. Several aryliodonium salts, aryliodonium
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Published 07 Feb 2018

Diels–Alder cycloadditions of N-arylpyrroles via aryne intermediates using diaryliodonium salts

  • Huangguan Chen,
  • Jianwei Han and
  • Limin Wang

Beilstein J. Org. Chem. 2018, 14, 354–363, doi:10.3762/bjoc.14.23

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  • Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China 10.3762/bjoc.14.23 Abstract With a strategy of the formation of benzynes by using diaryliodonium salts, a cycloaddition reaction of N-arylpyrroles with benzynes was reported. A
  • photosensitive dyes. Keywords: benzyne; cycloaddition; diaryliodonium salts; N-phenylamine; pyrrole; Introduction Pyrrole is a very useful heterocyclic substrate to produce structural attributes of valuable chemicals, functional materials and pharmaceuticals [1][2][3][4][5]. Recently, arylation of pyrrole
  • derivatives with diaryliodonium salts for pyrrole–aryl coupling products is generating tremendous academic interest in organic synthesis. In 2012, the Zhang and Yu group reported that sodium hydroxide promoted direct arylation of unprotected pyrroles with diaryliodonium salts at the temperature of 80 °C, the
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Published 06 Feb 2018

One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na2S2O8

  • Teppei Sasaki,
  • Katsuhiko Moriyama and
  • Hideo Togo

Beilstein J. Org. Chem. 2018, 14, 345–353, doi:10.3762/bjoc.14.22

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  • -alkynoates with N-bromosuccinimide (NBS) at rt [34], where those reactions proceed via radical spiro-cyclization and then radical 1,2-carboxyl group migration, were reported. On the other hand, diaryliodonium salts are very useful for the C-arylation of active CH groups, the O-arylation of OH groups, and the
  • N-arylation of NH groups under metal-free conditions [35][36][37][38][39]. For example, treatment of arenecarboxylic acids and alkanecarboxylic acids with diaryliodonium salts and t-BuOK under toluene refluxing conditions provides the corresponding aryl carboxylates in good yields [40][41]. However
  • , it is known that 4-arylcoumarins have antitumor activity [42]. Therefore, the one-pot preparation of 4-arylcoumarins from 3-aryl-2-alkynoic acids via aryl esters and cyclization is attractive and important. Here, as part of our ongoing investigation of the synthetic use of diaryliodonium salts for
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Published 05 Feb 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

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  • the corresponding sulfides. Very recently, the same group reported of a controllable sulfenylation and sulfoxidation procedure starting from alkyl and aryl thiosulfates and diaryliodonium salts under visible-light catalysis with Eosin Y (Scheme 40) [75]. They observed that the reaction yields the
  • diaryliodonium salts reacted efficiently with alkyl and aryl thiosulfate salts to the respective sulfide and sulfoxides. A row of functional groups like for example amines, cyano groups, esters, hydroxy groups or nitro groups were highly tolerated and gave the opportunity for late-stage functionalization of
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Published 05 Jan 2018

Cationic Pd(II)-catalyzed C–H activation/cross-coupling reactions at room temperature: synthetic and mechanistic studies

  • Takashi Nishikata,
  • Alexander R. Abela,
  • Shenlin Huang and
  • Bruce H. Lipshutz

Beilstein J. Org. Chem. 2016, 12, 1040–1064, doi:10.3762/bjoc.12.99

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  • conditions, as shown in Scheme 3 (left). By contrast, the Daugulis group and others [173][174] have demonstrated Pd-catalyzed ortho-arylations of anilides at temperatures typically greater than 100 °C, and the Sanford group has also studied similar transformations involving diaryliodonium salts [175
  • silver salt and HBF4 (or in situ generated AgBF4). The specific nature of the reaction between the palladacycle and aryl iodide and resulting intermediate is lacking in details. It is known that divalent palladacycles react with alkyl iodides or diaryliodonium salts, and this process likely involves a Pd
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Published 20 May 2016

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
  • diaryliodonium salts 2 to produce quinazolin-4(3H)-imine derivatives 3 with Cu(OTf)2 as the catalyst [13]. Encouraged by this finding, we initially attempted the reaction of o-cyanoaniline (1a) with di-(o-bromophenyl)iodonium salt 2. The reaction of 2 equiv of o-cyanoaniline (1a) with 2 in DCE at 110 °C for 6 h
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Published 30 Nov 2015

Coupling of C-nitro-NH-azoles with arylboronic acids. A route to N-aryl-C-nitroazoles

  • Marta K. Kurpet,
  • Aleksandra Dąbrowska,
  • Małgorzata M. Jarosz,
  • Katarzyna Kajewska-Kania,
  • Nikodem Kuźnik and
  • Jerzy W. Suwiński

Beilstein J. Org. Chem. 2013, 9, 1517–1525, doi:10.3762/bjoc.9.173

Graphical Abstract
  • . The presence of the nitro group (a strong electron-withdrawing substituent) in the azole entails the adjustment of the conditions of N-arylation reaction. Besides a very recently published approach involving N-arylation of nitroazoles with diaryliodonium salts [20], already described methods utilize
  • of coupling of diaryliodonium salts with 3-nitro-1H-pyrazole [20], a product of Ullman phenylation of 3-nitro-1H-pyrazole [34], or a byproduct in the synthesis of 1-phenyl-4-amino-5-methylaminopyridazin-6-one [17] (Scheme 1). Although these works describe 3-nitro-1-phenyl-1H-pyrazole (3a) as the
  • et al. [20], it appears that both methods are regioselective and lead to syntheses of N-aryl-C-nitroazoles in moderate to high yields. Arylboronic acids are more easily available than diaryliodonium salts, and thus the scope of our approach seems to be wider. The much milder reaction conditions
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Published 30 Jul 2013

Palladium-catalyzed synthesis of N-arylated carbazoles using anilines and cyclic diaryliodonium salts

  • Stefan Riedmüller and
  • Boris J. Nachtsheim

Beilstein J. Org. Chem. 2013, 9, 1202–1209, doi:10.3762/bjoc.9.136

Graphical Abstract
  • diaryliodonium salts by a ring opening/Buchwald-amination cascade using anilines and aliphatic amines as nitrogen-containing substrates. With 5 mol % of Pd(OAc)2 the desired N-arylcarbazoles could be isolated in up to 71% yield. Finally, the corresponding cyclic diarylbromonium derivatives were tested in the
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Published 21 Jun 2013

A practical microreactor for electrochemistry in flow

  • Kevin Watts,
  • William Gattrell and
  • Thomas Wirth

Beilstein J. Org. Chem. 2011, 7, 1108–1114, doi:10.3762/bjoc.7.127

Graphical Abstract
  • one-pot procedures to diaryliodonium salts known that involve both oxidation and ligand exchange directly from the aryl and iodoarene starting materials. The electrochemical oxidation of an iodoarene in the presence of another arene provides a quite general and simple one-step approach to the
  • synthesis of diaryliodonium salts [22]. We describe herein a simple procedure for the flow synthesis of diaryliodonium salts using the electrochemical microreactor device described above. The products were obtained in good yields and only minimal work-up was required after the reaction. The reaction takes
  • solvent was then removed, water was added (3 mL) and the iodide was precipitated by addition of KI (166 mg, 1 mmol) to give the diaryliodonium salts 11. Di-p-tolyliodonium iodide (11a) [24] Collection of 3 mL, yield: 100 mg (72%); colourless solid; mp 162–164 °C; 1H NMR (400 MHz, CDCl3) δ 2.27 (s, 6H
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Published 15 Aug 2011
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