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9 article(s) from Beier, Petr

Synthesis of sulfur karrikin bioisosteres as potential neuroprotectives

Martin Pošta,
Václav Zima,
Lenka Poštová Slavětínská,
Marika Matoušová and
Petr Beier

Full Research Paper
Published 16 May 2022

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1. Graphical Abstract
2. Figure 1: Structures of naturally occurring karrikins.
  
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3. Scheme 1: i) P₄S₁₀, THF; ii) 2-chloropropionyl chloride, Et₃N; iii) Ph₃P, NaOAc, Ac₂O.
  
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4. Figure 2: Target compounds with highlighted positions of oxygen to sulfur exchange.
  
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5. Scheme 2: i) Lawesson’s reagent, HMDO, toluene, MW irradiation, 120 °C, 60 min.
  
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6. Scheme 3: i) P₄S₁₀ or Lawesson’s reagent, see table for conditions; ii) 2-chloropropionyl chloride, Et₃N, DCM...
  
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7. Scheme 4: i) LiHMDS, MeI, THF, −78 °C.
  
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8. Scheme 5: i) a) NaOH, MeOH/H₂O, rt, Amberlyst 15 [H⁺], b) AcOH 70% aq, reflux, 2 h; ii) a) EtOCOCl, pyridine,...
  
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9. Scheme 6: i) Lawesson’s reagent, HMDO, toluene, MW irradiation (120 °C), 60 min.
  
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Beilstein J. Org. Chem. 2022, 18, 549–554, doi:10.3762/bjoc.18.57

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Ligand-dependent stereoselective Suzuki–Miyaura cross-coupling reactions of β-enamido triflates

Tomáš Chvojka,
Athanasios Markos,
Svatava Voltrová,
Radek Pohl and
Petr Beier

Letter
Published 29 Oct 2021

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1. Graphical Abstract
2. Scheme 1: A: Synthesis of (Z)-β-enamido triflates and subsequent stereoselective cross-coupling reactions. B:...
  
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3. Scheme 2: Substrate scope of the Suzuki coupling leading to enamides 2 and 3. ^aRatio determined by ¹⁹F NMR; ^b...
  
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4. Scheme 3: Proposed mechanisms for the formed Suzuki coupling retention products 2 and inversion products 3.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2021, 17, 2657–2662, doi:10.3762/bjoc.17.179

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Synthesis of N-perfluoroalkyl-3,4-disubstituted pyrroles by rhodium-catalyzed transannulation of N-fluoroalkyl-1,2,3-triazoles with terminal alkynes

Olga Bakhanovich,
Viktor Khutorianskyi,
Vladimir Motornov and
Petr Beier

Full Research Paper
Published 18 Feb 2021

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1. Graphical Abstract
2. Figure 1: Selected pyrrole-containing natural products, drugs, agrochemicals, and functional materials.
  
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3. Scheme 1: Transformation of N-sulfonyl-1,2,3-triazoles to pyrroles via metal iminocarbenes.
  
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4. Scheme 2: Transannulation of triazoles 2 with phenylacetylene.
  
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5. Scheme 3: Transannulation of N-perfluoroalkyl-1,2,3-triazoles with aliphatic alkynes.
  
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6. Scheme 4: Reaction of 1a with hex-5-ynenitrile.
  
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7. Scheme 5: Metalation and carboxylation of in situ-prepared pyrrole 2a.
  
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8. Scheme 6: Plausible mechanism for rhodium-catalyzed transannulation of N-perfluoroalkyl-1,2,3-triazoles with ...
  
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Beilstein J. Org. Chem. 2021, 17, 504–510, doi:10.3762/bjoc.17.44

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One-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates using Togni’s reagent

Azim Ziyaei Halimehjani,
Martin Dračínský and
Petr Beier

Letter
Published 24 Nov 2017

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1. Graphical Abstract
2. Scheme 1: Synthetic routes for the preparation of trifluoromethyl dithiocarbamates.
  
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3. Scheme 2: Synthesis of S-trifluoromethyl dithiocarbamates. Isolated yields are given in parentheses.
  
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4. Scheme 3: Formation of benzyl isothiocyanate in a reaction with benzylamine.
  
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5. Figure 1: Variable temperature ¹H NMR spectra of compound 4c (CH₂ region on the left and CH₃ region on the ri...
  
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6. Figure 2: The Eyring plot obtained for the rotation around the N–C bond in compound 4c.
  
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7. Figure 3: The optimized structure of compound 4b (left) and the transition state structure for the rotation a...
  
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Beilstein J. Org. Chem. 2017, 13, 2502–2508, doi:10.3762/bjoc.13.247

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Synthesis and nucleophilic aromatic substitution of 3-fluoro-5-nitro-1-(pentafluorosulfanyl)benzene

Javier Ajenjo,
Martin Greenhall,
Camillo Zarantonello and
Petr Beier

Full Research Paper
Published 03 Feb 2016

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1. Graphical Abstract
2. Scheme 1: Direct fluorination of 1,2-bis(3-nitrophenyl)disulfane.
  
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3. Scheme 2: Direct fluorination of 3-nitro-1-(pentafluorosulfanyl)benzene (1).
  
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4. Figure 1: Conversion vs added fluorine equivalents for the fluorination of 1 in MeCN (left) and anhydrous HF ...
  
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5. Scheme 3: Preparative fluorination of 3-nitro-1-(pentafluorosulfanyl)benzene (1).
  
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6. Scheme 4: Synthesis of 2 by fluorodenitration of 5.
  
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Beilstein J. Org. Chem. 2016, 12, 192–197, doi:10.3762/bjoc.12.21

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Synthesis and reactivity of aliphatic sulfur pentafluorides from substituted (pentafluorosulfanyl)benzenes

Norbert Vida,
Jiří Václavík and
Petr Beier

Full Research Paper
Published 20 Jan 2016

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1. Graphical Abstract
2. Scheme 1: Oxidation of SF₅-anisole and phenol. ¹⁹F NMR yields are shown (isolated yields in parentheses).
  
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3. Scheme 2: Proposed mechanism for the formation of 3 and 4 from SF₅ aromatics 1 and 2.
  
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4. Scheme 3: Oxidation of anisole 10 and phenol 11. ¹⁹F NMR yields are given.
  
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5. Scheme 4: Synthesis of para-benzoquinone 12 and oxidation to maleic acid 4. ¹⁹F NMR yields are shown, in pare...
  
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6. Scheme 5: Catalytic hydrogenation and Diels–Alder reaction of benzoquinone 12.
  
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7. Figure 1: Optimized geometries of transition states of Diels–Alder reaction of cyclopentadiene with 12. Selec...
  
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8. Scheme 6: Decomposition of 3 in water.
  
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9. Scheme 7: Formation of acids 5, 18 and 19 from lactone 3.
  
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10. Scheme 8: Synthesis of maleic anhydride 20 and Diels–Alder adducts 21.
  
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11. Scheme 9: Reaction of maleic acid 4 with diazomethane.
  
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12. Scheme 10: Decarboxylation of maleic acid 4 to acrylic acid 23 in DMSO and the preparation of deuterium labell...
  
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Beilstein J. Org. Chem. 2016, 12, 110–116, doi:10.3762/bjoc.12.12

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Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: Application to the synthesis of SF₅-substituted phenylboronic esters and iodobenzenes

George Iakobson,
Junyi Du,
Alexandra M. Z. Slawin and
Petr Beier

Full Research Paper
Published 26 Aug 2015

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1. Graphical Abstract
2. Scheme 1: Borylation of aryldiazonium tetrafluoroborates 3. Reaction conditions: 3 (1 mmol), B₂pin₂ (1 mmol),...
  
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3. Scheme 2: Proposed reaction mechanism.
  
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4. Scheme 3: Reaction of diazonium salt 3i under borylation conditions.
  
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5. Scheme 4: Suzuki–Miyaura reaction of boronates 2a and 2b with aryl iodides. Reaction conditions: 2 (1 mmol), ...
  
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6. Scheme 5: Syntesis of boronic acid 8b and trifluoroborates 9. Reaction conditions for the synthesis of 8b: 2 ...
  
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7. Scheme 6: Iodination of aryldiazonium tetrafluoroborates 3. Reaction conditions: 3 (1 mmol), I₂ (1.1 mmol), p...
  
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Beilstein J. Org. Chem. 2015, 11, 1494–1502, doi:10.3762/bjoc.11.162

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Synthesis of SF₅-containing benzisoxazoles, quinolines, and quinazolines by the Davis reaction of nitro-(pentafluorosulfanyl)benzenes

Petr Beier and
Tereza Pastýříková

Full Research Paper
Published 21 Feb 2013

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1. Graphical Abstract
2. Scheme 1: Proposed mechanism of the Davis reaction giving benzisoxazoles.
  
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3. Figure 1: Substitution products 1, oximes 2 and nitro-(pentafluorosulfanyl)benzenes 3 and 4.
  
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4. Scheme 2: Synthesis of SF₅-substituted quinolines and mefloquine analogues by Wipf and co-workers [29,30].
  
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5. Scheme 3: Synthesis of quinoline 12.
  
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6. Scheme 4: Synthesis of quinoline 13.
  
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7. Scheme 5: Synthesis of quinazoline 14.
  
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Beilstein J. Org. Chem. 2013, 9, 411–416, doi:10.3762/bjoc.9.43

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Highly selective synthesis of (E)-alkenyl-(pentafluorosulfanyl)benzenes through Horner–Wadsworth–Emmons reaction

George Iakobson and
Petr Beier

Full Research Paper
Published 25 Jul 2012

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1. Graphical Abstract
2. Scheme 1: Proposed synthesis of alkenyl-(pentafluorosulfanyl)benzenes.
  
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3. Scheme 2: Reactive intermediates involved in HWE reactions to alkenes 5 and 6.
  
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4. Scheme 3: Diazotization/reduction of 8d to 9d and the formation of unexpected cyclized product 10d.
  
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5. Scheme 4: Synthesis of substituted phenanthrene 11d.
  
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6. Scheme 5: Synthesis of phosphonate 12 and SF₅-stilbene derivative 13d.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2012, 8, 1185–1190, doi:10.3762/bjoc.8.131

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