Table of Contents
14	Full Research Paper
4	Letter
4	Review

Molecular basis for protein–protein interactions

Brandon Charles Seychell and
Tobias Beck

Review
Published 04 Jan 2021

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1. Graphical Abstract
2. Figure 1: Different methodologies employed to study PPIs. The protein used for illustration is the heterodime...
  
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3. Figure 2: Mechanisms of homooligomeric complex formations. a) Domain swapping of RNase A (PDB: 1A2W) [73]. The sw...
  
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4. Figure 3: Parts a) and b) represent the electron densities and B-factors of TMV, respectively. The cryo-EM st...
  
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5. Figure 4: Schematic of the general assembly of charged protein containers to form binary nanoparticle superla...
  
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Beilstein J. Org. Chem. 2021, 17, 1–10, doi:10.3762/bjoc.17.1

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Synthesis, crystal structures and properties of carbazole-based [6]helicenes fused with an azine ring

Daria I. Tonkoglazova,
Anna V. Gulevskaya,
Konstantin A. Chistyakov and
Olga I. Askalepova

Full Research Paper
Published 04 Jan 2021

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1. Graphical Abstract
2. Scheme 1: Overview of the synthetic methods for the carbazole-based heterohelicenes. i) Pd₂dba₃, xantphos, K₃...
  
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3. Scheme 2: Synthetic strategy for the carbazole-based [6]helicenes fused with an azine ring.
  
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4. Scheme 3: Sonogashira coupling of compound 4b with phenylacetylene. i) Pd(PPh₃)₂Cl₂, CuI, iPr₂NH, DMSO, 80 °C...
  
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5. Figure 1: Molecular structure of carbazole-based [6]helicenes 10a (a), 10b (b) and 10c (c) (X-ray data).
  
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6. Figure 2: Crystal packing of carbazole-based [6]helicenes 10a (a, b), 10b (c,d) and 10c (e). Hydrogen atoms a...
  
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Beilstein J. Org. Chem. 2021, 17, 11–21, doi:10.3762/bjoc.17.2

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The fluorescence of a mercury probe based on osthol

Guangyan Luo,
Zhishu Zeng,
Lin Zhang,
Zhu Tao and
Qianjun Zhang

Full Research Paper
Published 05 Jan 2021

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1. Graphical Abstract
2. Figure 1: (A) Fluorescence spectra of OST (c = 3.0 × 10⁻⁵ mol∙L⁻¹) upon the addition of various metal ions. (...
  
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3. Figure 2: Metal ion selectivity of OST–Hg²⁺ (c = 3.0 × 10⁻⁵ mol∙L⁻¹) in the presence of 1.2 × 10⁻⁴ mol∙L⁻¹ of...
  
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4. Figure 3: Fluorescence spectra of OST (c = 3 × 10⁻⁵ mol∙L⁻¹) in H₂O/CH₃OH 97:3, v/v in the presence of an inc...
  
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5. Figure 4: The standard Job curve of mercury ions to OST (c = 3.0 × 10⁻⁵ mol∙L⁻¹) at 406 nm (pH 7.0, H₂O/CH₃OH...
  
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6. Figure 5: Mass spectrum of the probe with Hg²⁺.
  
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7. Figure 6: ¹H NMR titration spectra recorded for OST (c = 5 × 10⁻⁴ mol∙L⁻¹) during the addition of different m...
  
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8. Figure 7: The binding mode of OST and Hg²⁺.
  
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Beilstein J. Org. Chem. 2021, 17, 22–27, doi:10.3762/bjoc.17.3

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Recent progress in the synthesis of homotropane alkaloids adaline, euphococcinine and N-methyleuphococcinine

Dimas J. P. Lima,
Antonio E. G. Santana,
Michael A. Birkett and
Ricardo S. Porto

Review
Published 05 Jan 2021

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1. Graphical Abstract
2. Figure 1: Homotropane (azabicyclononane) systems.
  
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3. Figure 2: Alkaloids (−)-adaline (1), (+)-euphococcinine (2) and (+)-N-methyleuphococcinine (3).
  
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4. Scheme 1: Synthetic strategies before 1995.
  
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5. Scheme 2: Synthesis (±)-adaline (1) and (±)-euphococcinine (2). Reagents and conditions: i) 1. dihydropyran, ...
  
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6. Scheme 3: Synthesis (+)-euphococcinine (2). Reagents and conditions: i) H₂O₂, SeO₂ (cat), acetone, rt, 88%; i...
  
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7. Scheme 4: Synthesis (+)-euphococcinine (2). Reagents and conditions: i) 2,4-bis(4-phenoxyphenyl)-1,3-dithia-2...
  
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8. Scheme 5: Synthesis of (±)-euphococcinine precursor (±)-42. Reagents and conditions: i) Bu₃SnH, AIBN, toluene...
  
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9. Scheme 6: Synthesis of (−)-adaline (1). Reagents and conditions: i) LiH₂NBH₃, THF, 40 °C, 88%; ii) TPAP, NMO,...
  
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10. Scheme 7: Synthesis of (−)-adaline (1) and (−)-euphococcinine (2). Reagents and conditions: i) 1. BuLi, t-BuO...
  
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11. Scheme 8: Synthesis of (−)-adaline (1). Reagents and conditions: i) Ref. [52]; ii) Et₃N, TBDMSOTf, CH₂Cl₂, 0 °C t...
  
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12. Scheme 9: Synthesis of (+)-euphococcinine (2). Reagents and conditions: i) 1. Cp₂ZrCl₂,AlMe₃, CH₂Cl₂; 2. p-me...
  
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13. Scheme 10: Synthesis of (−)-adaline 1. Reagents and conditions: i) 1. CuBr^.DMS, Et₂O/DMS, -42 ºC; 2. 1-heptyne...
  
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14. Scheme 11: Synthesis of (−)-euphococcinine (2) and (−)-adaline (1). Reagents and conditions: i) 102, KHMDS, Et₂...
  
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15. Scheme 12: Synthesis of N-methyleuphococcinine 3. Reagents and conditions: i) 108 (1.5 equiv), 3,5-di-F-C₆H₃B(...
  
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Beilstein J. Org. Chem. 2021, 17, 28–41, doi:10.3762/bjoc.17.4

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Control over size, shape, and photonics of self-assembled organic nanocrystals

Chen Shahar,
Yaron Tidhar,
Yunmin Jung,
Haim Weissman,
Sidney R. Cohen,
Ronit Bitton,
Iddo Pinkas,
Gilad Haran and
Boris Rybtchinski

Full Research Paper
Published 06 Jan 2021

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1. Graphical Abstract
2. Figure 1: Chemical structure of compound 1 and UV–vis spectra in an aggregating aqueous medium and in the dis...
  
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3. Figure 2: Transmission electron microscopy (TEM) images (left, zoomed-out and zoomed-in; 1 × 10⁻⁴ M solutions...
  
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4. Figure 3: Cryo-TEM images of a 1 × 10⁻⁴ M solution of 1 (5% THF) and the corresponding molecular model as wel...
  
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5. Figure 4: Cryo-TEM images of 1 × 10⁻⁴ M compound 1 in THF/water solutions after one minute of aging. A) 5% TH...
  
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6. Figure 5: Transient kinetics at different laser powers probed at 755 nm (1 × 10⁻⁴ M solution at pH 10): A) 5%...
  
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Beilstein J. Org. Chem. 2021, 17, 42–51, doi:10.3762/bjoc.17.5

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Circularly polarized luminescent systems fabricated by Tröger's base derivatives through two different strategies

Cheng Qian,
Yuan Chen,
Qian Zhao,
Ming Cheng,
Chen Lin,
Juli Jiang and
Leyong Wang

Letter
Published 06 Jan 2021

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1. Graphical Abstract
2. Scheme 1: Cartoon representative for rac-TBPP-based CPL-active systems fabricated through two strategies.
  
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3. Figure 1: Ground-state and excited-state chirality of R_2N-TBPP and S_2N-TBPP. (a) CD spectra of R_2N-TBPP and S...
  
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4. Figure 2: (a) Fluorescence spectra of rac-TBPP in solution (dash line) and in the rac-TBPP/DGG co-gels. (b) C...
  
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5. Figure 3: (a) UV–vis absorption spectra of rac-TBPP and rac-TBPP/DGG co-gel (rac-TBPP/DGG = 1:80). (b) FTIR s...
  
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Beilstein J. Org. Chem. 2021, 17, 52–57, doi:10.3762/bjoc.17.6

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Progress in the total synthesis of inthomycins

Bidyut Kumar Senapati

Review
Published 07 Jan 2021

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1. Graphical Abstract
2. Figure 1: The inthomycins A–C (1–3) and structurally closely related compounds.
  
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3. Figure 2: Syntheses of inthomycins A–C (1–3).
  
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4. Scheme 1: The first total synthesis of racemic inthomycin A (rac)-1 by Whiting.
  
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5. Scheme 2: Moloney’s synthesis of the phenyl analogue of inthomycin C ((rac)-3).
  
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6. Scheme 3: Moloney’s synthesis of phenyl analogues of inthomycins A (rac-1) and B (rac-2).
  
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7. Scheme 4: The first total synthesis of inthomycin B (+)-2 by R. J. K. Taylor.
  
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8. Scheme 5: R. J. K. Taylor’s total synthesis of racemic inthomycin A (rac)-1.
  
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9. Scheme 6: The first total synthesis of inthomycin C ((+)-3) by R. J. K. Taylor.
  
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10. Scheme 7: The first total synthesis of naturally occurring inthomycin C ((–)-3) by Ryu et al.
  
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11. Scheme 8: Preparation of E,E-iododiene (+)-84 and Z,E- iododiene 85a.
  
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12. Scheme 9: Hatakeyama’s total synthesis of inthomycin A (+)-1 and inthomycin B (+)-2.
  
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13. Scheme 10: Hatakeyama’s total synthesis of inthomycin C ((–)-3).
  
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14. Scheme 11: Maulide’s formal synthesis of racemic inthomycin C ((rac)-3).
  
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15. Scheme 12: Hale’s synthesis of dienylstannane (+)-69 and enyne (+)-82b intermediates.
  
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16. Scheme 13: Hale’s total synthesis of inthomycin C ((+)-3).
  
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17. Scheme 14: Hale and Hatakeyama’s resynthesis of (3R)-inthomycin C (−)-3 Mosher esters.
  
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18. Scheme 15: Reddy’s formal syntheses of inthomycin C (+)-3 and inthomycin C ((−)-3).
  
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19. Scheme 16: Synthesis of the cross-metathesis precursors (rac)-118 and 121.
  
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20. Scheme 17: Donohoe’s total synthesis of inthomycin C ((−)-3).
  
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21. Scheme 18: Synthesis of dienylboronic ester (E,E)-128.
  
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22. Scheme 19: Synthesis of the alkenyl iodides (Z)- and (E)-130.
  
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23. Scheme 20: Burton’s total synthesis of inthomycin B ((+)-2).
  
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24. Scheme 21: Burton’s total synthesis of inthomycin C ((−)-3).
  
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25. Scheme 22: Burton’s total synthesis of inthomycin A ((+)-1).
  
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26. Scheme 23: Synthesis of common intermediate (Z)-(+)-143a.
  
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27. Scheme 24: Synthesis of (Z)-and (E)-selective fragments (+)-145a–c.
  
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28. Scheme 25: Kim’s total synthesis of inthomycins A (+)-1 and B (+)-2.
  
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29. Scheme 26: Completion of total synthesis of inthomycin C ((–)-3) by Kim.
  
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Beilstein J. Org. Chem. 2021, 17, 58–82, doi:10.3762/bjoc.17.7

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Benzothiazolium salts as reagents for the deoxygenative perfluoroalkylthiolation of alcohols

Armin Ariamajd,
Nils J. Gerwien,
Benjamin Schwabe,
Stefan Dix and
Matthew N. Hopkinson

Letter
Published 08 Jan 2021

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1. Graphical Abstract
2. Scheme 1: Synthetic routes towards perfluoroalkyl thioethers.
  
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3. Scheme 2: Two-step synthesis of BT-SR_F reagents from MBT.
  
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4. Scheme 3: Plausible mechanism for the formation of thioether 3 and thionoester 4.
  
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5. Scheme 4: Scope of the deoxygenative perfluoroalkylthiolation reaction using BT-SC₂F₅ and BT-SC₃F₇.
  
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Beilstein J. Org. Chem. 2021, 17, 83–88, doi:10.3762/bjoc.17.8

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Synthesis of aryl 2-bromo-2-chloro-1,1-difluoroethyl ethers through the base-mediated reaction between phenols and halothane

Yukiko Karuo,
Ayaka Kametani,
Atsushi Tarui,
Kazuyuki Sato,
Kentaro Kawai and
Masaaki Omote

Full Research Paper
Published 11 Jan 2021

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1. Graphical Abstract
2. Figure 1: Medical compounds having a difluoromethyl group.
  
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3. Scheme 1: Methods for the synthesis of ethers containing fluorine substituents.
  
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4. Scheme 2: The previous work reported by Yagupol’skii et al.
  
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5. Scheme 3: Intramolecular 1,4-addition of 2o.
  
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6. Scheme 4: Proposed reaction mechanism.
  
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Beilstein J. Org. Chem. 2021, 17, 89–96, doi:10.3762/bjoc.17.9

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Supramolecular polymerization of sulfated dendritic peptide amphiphiles into multivalent L-selectin binders

David Straßburger,
Svenja Herziger,
Katharina Huth,
Moritz Urschbach,
Rainer Haag and
Pol Besenius

Full Research Paper
Published 12 Jan 2021

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1. Graphical Abstract
2. Scheme 1: The synthesis of the C₃-symmetrical tetraethylene glycol-decorated peptide amphiphile I and the azi...
  
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3. Scheme 2: Synthesis of the sulfated peptide amphiphile II by copper-catalyzed azide–alkyne cyclization.
  
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4. Figure 1: Analysis of the self-assembly behavior of I by A: CD-spectra of 5, 10, 25 or 50 µM aqueous solution...
  
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5. Figure 2: Analysis of the supramolecular polymerization of II by A: CD-spectra of a 25 µM solution in TRIS bu...
  
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6. Figure 3: Concentration-dependent relative L-selectin binding of the supramolecular polymers I and II in HEPE...
  
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Beilstein J. Org. Chem. 2021, 17, 97–104, doi:10.3762/bjoc.17.10

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Supramolecular polymers with reversed viscosity/temperature profile for application in motor oils

Jan-Erik Ostwaldt,
Christoph Hirschhäuser,
Stefan K. Maier,
Carsten Schmuck and
Jochen Niemeyer

Full Research Paper
Published 12 Jan 2021

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1. Graphical Abstract
2. Figure 1: a) VII systems described by Sijbesma and Meijer, featuring two ureidopyrimidone BUs which are linke...
  
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3. Figure 2: a) GCP and ACP motif, as charged and neutral BUs and BINAM as precoordinating LU. b) Compounds 1, 2...
  
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4. Figure 3: Synthesis of compounds 1 to 4. Reagents and conditions: i) ʟ-Boc-glutamic acid benzyl ester, HCTU, ...
  
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5. Figure 4: a) 2D-screening in DMSO of the GCP derivative 1, specific viscosity vs concentration vs temperature...
  
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6. Figure 5: Comparison of the specific viscosities in dependence of the temperature of the ACP derivative (oran...
  
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7. Figure 6: DLS measurement of compound 2 in toluene at 25 °C, 60 °C and 100 °C.
  
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8. Figure 7: Specific viscosity of compounds 2, 3 and 4 in Nynas NS8 in dependency to the temperature.
  
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9. Figure 8: Specific viscosity of compound 4 in Nynas NS8 and Nexbase 3020.
  
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Beilstein J. Org. Chem. 2021, 17, 105–114, doi:10.3762/bjoc.17.11

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Direct synthesis of anomeric tetrazolyl iminosugars from sugar-derived lactams

Michał M. Więcław and
Bartłomiej Furman

Full Research Paper
Published 13 Jan 2021

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1. Graphical Abstract
2. Scheme 1: Our previous eﬀorts in the field of functionalization of sugar-derived lactams.
  
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3. Figure 1: Key concepts behind the goal of this work [34].
  
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4. Scheme 2: Preliminary experiment in search of a procedure for the synthesis of 2-(1H-tetrazol-5-yl)-iminosuga...
  
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5. Scheme 3: Synthesis of a new class of alkaloid scaﬀold using the presented methodology.
  
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6. Scheme 4: Synthesis of a new, chiral 2-(tetrazol-5-yl)-iminosugar based potential organocatalyst.
  
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7. Scheme 5: Principle behind Woerpel’s model for prediction of the direction of nucleophile addition to oxocarb...
  
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8. Scheme 6: Diﬀerence in conformational stability of glucose- and galactose-derived iminium cations and the maj...
  
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9. Figure 2: ORTEP structures of compounds 3a and 3e obtained by X-ray analysis. Hydrogen atoms and benzyl group...
  
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10. Figure 3: Proposed structures of compounds 5a and 2-epi-5a with ¹H-¹H couplings and NOE eﬀects shown.
  
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11. Scheme 7: Proposed reaction mechanism for the described Ugi–azide reaction variant.
  
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12. Scheme 8: Possible pathway for spontaneous imine formation. Values reported are in kcal·mol⁻¹.
  
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13. Scheme 9: A possible path for tetrazole formation in the described conditions. Values reported are in kcal·mol...
  
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Beilstein J. Org. Chem. 2021, 17, 115–123, doi:10.3762/bjoc.17.12

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Tuning the solid-state emission of liquid crystalline nitro-cyanostilbene by halogen bonding

Subrata Nath,
Alexander Kappelt,
Matthias Spengler,
Bibhisan Roy,
Jens Voskuhl and
Michael Giese

Letter
Published 14 Jan 2021

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1. Graphical Abstract
2. Figure 1: Schematic representation of the modular approach towards halogen-bonded fluorescent liquid crystals....
  
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3. Figure 2: Representative POM images of NO₂-C₁₀ at 94 °C (a) and NO₂-C₁₀∙∙∙F₄Az at 61.5 °C (b) upon cooling fr...
  
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4. Figure 3: Comparison of the mesomorphic properties of NO₂-C_n, NO₂-C_n∙∙∙F₄St, and NO₂-C_n∙∙∙F₄Az (n = 8–11). Th...
  
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5. Figure 4: Graphical representation of the calculated interaction energies in kJ/mol of the XB-acceptor NO₂-C₁...
  
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6. Figure 5: Summary of the thermal behaviour of the azo complexes with decreasing fluorination degree as observ...
  
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7. Figure 6: POM images of the supramolecular assemblies NO₂-C₁₀∙∙∙F₃Az (a), NO₂-C₁₀∙∙∙F₂Az (b) and NO₂-C₁₀∙∙∙F₂...
  
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8. Figure 7: Fluorescence studies of NO₂-C₉∙∙∙F₄St. The photographs of the solid components as well as the forme...
  
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9. Figure 8: Photographs of the assemblies with different alkoxy chain lengths on the NO₂-C_n moiety directly aft...
  
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10. Figure 9: Temperature-dependent fluorescent images of NO₂-C₉∙∙∙F₄St showing the enhancement of emission upon ...
  
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Beilstein J. Org. Chem. 2021, 17, 124–131, doi:10.3762/bjoc.17.13

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Facile preparation and conversion of 4,4,4-trifluorobut-2-yn-1-ones to aromatic and heteroaromatic compounds

Takashi Yamazaki,
Yoh Nakajima,
Minato Iida and
Tomoko Kawasaki-Takasuka

Full Research Paper
Published 15 Jan 2021

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1. Graphical Abstract
2. Scheme 1: Deacetylative cyclization of 3fa.
  
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Beilstein J. Org. Chem. 2021, 17, 132–138, doi:10.3762/bjoc.17.14

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Insight into functionalized-macrocycles-guided supramolecular photocatalysis

Minzan Zuo,
Krishnasamy Velmurugan,
Kaiya Wang,
Xueqi Tian and
Xiao-Yu Hu

Review
Published 18 Jan 2021

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1. Graphical Abstract
2. Figure 1: Chemical structures of representative macrocycles.
  
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3. Figure 2: Ba²⁺-induced intermolecular [2 + 2]-photocycloaddition of crown ether-functionalized substrates 1 a...
  
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4. Figure 3: Energy transfer system constructed of a BODIPY–zinc porphyrin–crown ether triad assembly bound to a...
  
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5. Figure 4: The sensitizer 5 was prepared by a flavin–zinc(II)–cyclen complex for the photooxidation of benzyl ...
  
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6. Figure 5: Enantiodifferentiating Z–E photoisomerization of cyclooctene sensitized by a chiral sensitizer as t...
  
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7. Figure 6: Structures of the modified CDs as chiral sensitizing hosts. Adapted with permission from [24], Copyrigh...
  
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8. Figure 7: Supramolecular 1:1 and 2:2 complexations of AC with the cationic β-CD derivatives 16–21 and subsequ...
  
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9. Figure 8: Construction of the TiO₂–AuNCs@β-CD photocatalyst. Republished with permission of The Royal Society...
  
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10. Figure 9: Visible-light-driven conversion of benzyl alcohol to H₂ and a vicinal diol or to H₂ and benzaldehyd...
  
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11. Figure 10: (a) Structures of CDs, (b) CoPyS, and (c) EY. Republished with permission of The Royal Society of C...
  
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12. Figure 11: Conversion of CO₂ to CO by ReP/HO-TPA–TiO₂. Republished with permission of The Royal Society of Che...
  
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13. Figure 12: Thiacalix[4]arene-protected TiO₂ clusters for H₂ evolution. Reprinted with permission from [37], Copyri...
  
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14. Figure 13: 4-Methoxycalix[7]arene film-based TiO₂ photocatalytic system. Reprinted from [38], Materials Today Chem...
  
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15. Figure 14: (a) Photodimerization of 6-methylcoumarin (22). (b) Catalytic cycle for the photodimerization of 22...
  
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16. Figure 15: Formation of a supramolecular PDI–CB[7] complex and structures of monomers and the chain transfer a...
  
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17. Figure 16: Ternary self-assembled system for photocatalytic H₂ evolution (a) and structure of 27 (b). Figure 16 reprodu...
  
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18. Figure 17: Structures of COP-1, CMP-1, and their substrate S-1 and S-2.
  
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19. Figure 18: Supramolecular self-assembly of the light-harvesting system formed by WP5, β-CAR, and Chl-b. Reprod...
  
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20. Figure 19: Photocyclodimerization of AC based on WP5 and WP6.
  
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Beilstein J. Org. Chem. 2021, 17, 139–155, doi:10.3762/bjoc.17.15

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Novel library synthesis of 3,4-disubstituted pyridin-2(1H)-ones via cleavage of pyridine-2-oxy-7-azabenzotriazole ethers under ionic hydrogenation conditions at room temperature

Romain Pierre,
Anne Brethon,
Sylvain A. Jacques,
Aurélie Blond,
Sandrine Chambon,
Sandrine Talano,
Catherine Raffin,
Branislav Musicki,
Claire Bouix-Peter,
Loic Tomas,
Gilles Ouvry,
Rémy Morgentin,
Laurent F. Hennequin and
Craig S. Harris

Full Research Paper
Published 18 Jan 2021

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1. Graphical Abstract
2. Figure 1: Retrosynthetic disconnection of our privileged kinase scaffold 1.
  
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3. Scheme 1: Reagents and conditions: (a) MeOH, DIPEA, reflux, 70%; b) TBTU, DIPEA, DMF, rt, 91%.
  
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4. Scheme 2: Proposed mechanistic explanation for the liberation of the Pd catalytic cycle after addition of sac...
  
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5. Scheme 3: Formation of C2–OAt ether 15 using HATU. Reagents and condtions: (a) HATU, DIPEA, DCM, rt, 16 h, ((...
  
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6. Scheme 4: Proposed mechanistic pathways for the transformation of Py–OAt ethers 17 to the pyridin-2H-one 1 mo...
  
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7. Scheme 5: Failure to exploit logical convergent building block 26. Reagents and conditions: a) HATU, DIPEA, D...
  
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8. Scheme 6: Library route to 32. Reagents and conditions: a) 4 M HCl_aq, reflux, 1 h, 81%; (b) EDCI, pyridine, P...
  
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Beilstein J. Org. Chem. 2021, 17, 156–165, doi:10.3762/bjoc.17.16

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Multiswitchable photoacid–hydroxyflavylium–polyelectrolyte nano-assemblies

Alexander Zika and
Franziska Gröhn

Full Research Paper
Published 19 Jan 2021

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1. Graphical Abstract
2. Scheme 1: The chemical network of reactions for 4-hydroxyflavylium (left) and the write-lock-erase cycle (rig...
  
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3. Scheme 2: The building blocks used for the self-assembly in this study: pelargonidin chloride (Flavy), 1-naph...
  
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4. Scheme 3: Overview of the different states of the multi-switchable system consisting of Flavy, 1N36S, and pol...
  
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5. Figure 1: Top: pelargonidin cation (Flavy) and network of chemical reactions; bottom: corresponding UV–vis sp...
  
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6. Figure 2: Characterization of Flavy: a) ¹H NMR spectrum at pH 7.0 (form A) before and after irradiation; b) ¹³...
  
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7. Scheme 4: Overview of the different states of the two main cycles switching the system consisting of 1N36S, F...
  
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8. Figure 3: UV–vis spectroscopy of the ternary nano-assemblies for cycle I (a) and cycle II (b).
  
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9. Figure 4: Dynamic light scattering: Electric field autocorrelation function g₁(τ) and distribution of relaxat...
  
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10. Figure 5: Static light scattering data from the assemblies of cycle I; a) A, non-irradiated, spherical partic...
  
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11. Figure 6: Comparison of cycle I and cycle II in AFM.
  
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12. Figure 7: a) ζ-Potential and b) effective surface charge density for cycle I; c) ζ-potential and d) effective...
  
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13. Figure 8: Isothermal titration calorimetry of poly(allylamine) into the cell containing Flavy and 1N36S in aq...
  
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14. Figure 9: Polar surface area of Flavy in form of A (left) and B (right).
  
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15. Figure 10: Hydrodynamic radii of the nano-assemblies as function of the loading ratio: a) cycle I, b) cycle II....
  
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16. Figure 11: UV–vis spectra of the nano-assemblies of cycle II at l = 0.75.
  
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17. Figure 12: ζ-Potential of the nano-assemblies of cycle II depending on the concentration ratio.
  
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18. Scheme 5: Different mixing orders of the assemblies. The major part of this study focuses on route i.
  
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Beilstein J. Org. Chem. 2021, 17, 166–185, doi:10.3762/bjoc.17.17

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Au(III) complexes with tetradentate-cyclam-based ligands

Ann Christin Reiersølmoen,
Thomas N. Solvi and
Anne Fiksdahl

Full Research Paper
Published 19 Jan 2021

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1. Graphical Abstract
2. Scheme 1: Synthetic protocols for the preparation of potential ligands 1–4.
  
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3. Scheme 2: Reduction of diamides 1a,b and tetraamides 2a,b.
  
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4. Scheme 3: Au(III) coordination conditions for ligands 5a,b and 6a,b. Coordination of 5b was unsuccessful.
  
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5. Figure 1: ¹H NMR study of the formation of complex 6a-Au(III) by AuCl₃ coordination to ligand 6a.
  
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Beilstein J. Org. Chem. 2021, 17, 186–192, doi:10.3762/bjoc.17.18

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1,2,3-Triazoles as leaving groups in S_NAr–Arbuzov reactions: synthesis of C6-phosphonated purine derivatives

Kārlis-Ēriks Kriķis,
Irina Novosjolova,
Anatoly Mishnev and
Māris Turks

Full Research Paper
Published 20 Jan 2021

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1. Graphical Abstract
2. Scheme 1: Structural diversity and synthetic methods of purinylphosphonates. MWI = microwave irradiation; LG ...
  
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3. Scheme 2: Synthetic routes for the formation of purinylphosphonates 4.
  
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4. Scheme 3: Synthesis of phosphonates 2, 7, and 8.
  
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5. Scheme 4: Synthesis of phosphonic acid monoesters 3 and 7–9 as well as phosphonic acid 10.
  
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6. Figure 1: Screenings of the rate for the ester group cleavage (conversion determined by NMR spectroscopy) in ...
  
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7. Scheme 5: Synthesis of 2,6-bistriazolylpurine derivatives 6a–i.
  
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8. Scheme 6: S_NAr–Arbuzov reaction between the bistriazolylpurines 6a–i and P(OEt)₃.
  
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9. Figure 2: Single-crystal X-ray analysis of diethyl (9-heptyl-2-(4-phenyl-1H-1,2,3-triazol-1-yl)-9H-purin-6-yl...
  
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Beilstein J. Org. Chem. 2021, 17, 193–202, doi:10.3762/bjoc.17.19

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A sustainable strategy for the straightforward preparation of 2H-azirines and highly functionalized NH-aziridines from vinyl azides using a single solvent flow-batch approach

Michael Andresini,
Leonardo Degannaro and
Renzo Luisi

Letter
Published 20 Jan 2021

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1. Graphical Abstract
2. Scheme 1: Flow generation and transformation of 2H-azirines.
  
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3. Scheme 2: Flow synthesis of 2H-azirines from vinyl azides. ^aThe solution of vinyl azide was re-introduced twi...
  
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4. Scheme 3: Mixed flow-batch approach for the preparation of functionalized NH-aziridines from vinyl azides.
  
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Beilstein J. Org. Chem. 2021, 17, 203–209, doi:10.3762/bjoc.17.20

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Exploring the possibility of using fluorine-involved non-conjugated electron-withdrawing groups for thermally activated delayed fluorescence emitters by TD-DFT calculation

Dongyang Chen and
Eli Zysman-Colman

Full Research Paper
Published 21 Jan 2021

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1. Graphical Abstract
2. Figure 1: Molecular structures of emitters discussed in this work.
  
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3. Figure 2: a) Calculated HOMO, LUMO, S₁ and T₁ energies, as well as HOMO and LUMO topologies of PhCF₃, PhOCF₃, ...
  
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4. Figure 3: Calculated HOMO, LUMO, S₁ and T₁ energies, as well as HOMO and LUMO topologies of 2CzCF₃, 2CzOCF₃, ...
  
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5. Figure 4: Calculated HOMO, LUMO, S₁ and T₁ energies, as well as HOMO and LUMO topologies of 2CzBN, 2CzTRZ, an...
  
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6. Figure 5: HOMO and LUMO distribution, HONTO and LUNTO of lowest singlet (S₁) and triplet excited (T₁) states ...
  
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7. Figure 6: HOMO and LUMO distribution, HONTO and LUNTO of lowest singlet (S₁) and triplet excited (T₁) states ...
  
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8. Figure 7: Calculated HOMO, LUMO, S₁ and T₁ energies, as well as HOMO and LUMO topologies of 5CzCF₃, 5CzOCF₃, ...
  
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9. Figure 8: Calculated HOMO, LUMO, S₁ and T₁ energies, as well as HOMO and LUMO topologies of 5CzBN, 5CzTRZ, an...
  
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10. Figure 9: HOMO and LUMO distribution, HONTO and LUNTO of lowest singlet (S₁) and triplet excited (T₁) states ...
  
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11. Figure 10: HOMO and LUMO distribution, HONTO and LUNTO of lowest singlet (S₁) and triplet excited (T₁) states ...
  
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12. Figure 11: HONTOs and LUNTOs of 2CzCF₃ in higher excited states (isovalue = 0.02).
  
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13. Figure 12: HONTOs and LUNTOs of 5CzCF₃ in higher excited states (isovalue = 0.02).
  
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Beilstein J. Org. Chem. 2021, 17, 210–223, doi:10.3762/bjoc.17.21

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Total synthesis of decarboxyaltenusin

Lucas Warmuth,
Aaron Weiß,
Marco Reinhardt,
Anna Meschkov,
Ute Schepers and
Joachim Podlech

Full Research Paper
Published 22 Jan 2021

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1. Graphical Abstract
2. Scheme 1: Biphenyl-derived mycotoxins.
  
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3. Scheme 2: Synthesis of arylboronates 6. Conditions: a) TBSCl, DMAP, imidazole, DMF, 50 °C, 4 h (96%); b) NBS,...
  
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4. Scheme 3: Synthesis of aryl bromides 9. Conditions: f) BBr₃, −78 °C to rt, 18 h (71%); g) R = TBS: TBSCl, DMA...
  
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5. Scheme 4: Final steps in the synthesis of biaryl 1. Conditions: h) Pd(OAc)₂, SPhos, Cs₂CO₃, dioxane/H₂O 7:1, ...
  
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Beilstein J. Org. Chem. 2021, 17, 224–228, doi:10.3762/bjoc.17.22

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Volume No. 17

2021

Pages 1 - 228

Table of Contents

Molecular basis for protein–protein interactions

Synthesis, crystal structures and properties of carbazole-based [6]helicenes fused with an azine ring

The fluorescence of a mercury probe based on osthol

Recent progress in the synthesis of homotropane alkaloids adaline, euphococcinine and N-methyleuphococcinine

Control over size, shape, and photonics of self-assembled organic nanocrystals

Circularly polarized luminescent systems fabricated by Tröger's base derivatives through two different strategies

Progress in the total synthesis of inthomycins

Benzothiazolium salts as reagents for the deoxygenative perfluoroalkylthiolation of alcohols

Synthesis of aryl 2-bromo-2-chloro-1,1-difluoroethyl ethers through the base-mediated reaction between phenols and halothane

Supramolecular polymerization of sulfated dendritic peptide amphiphiles into multivalent L-selectin binders

Supramolecular polymers with reversed viscosity/temperature profile for application in motor oils

Direct synthesis of anomeric tetrazolyl iminosugars from sugar-derived lactams

Tuning the solid-state emission of liquid crystalline nitro-cyanostilbene by halogen bonding

Facile preparation and conversion of 4,4,4-trifluorobut-2-yn-1-ones to aromatic and heteroaromatic compounds

Insight into functionalized-macrocycles-guided supramolecular photocatalysis

Novel library synthesis of 3,4-disubstituted pyridin-2(1H)-ones via cleavage of pyridine-2-oxy-7-azabenzotriazole ethers under ionic hydrogenation conditions at room temperature

Multiswitchable photoacid–hydroxyflavylium–polyelectrolyte nano-assemblies

Au(III) complexes with tetradentate-cyclam-based ligands

1,2,3-Triazoles as leaving groups in S_NAr–Arbuzov reactions: synthesis of C6-phosphonated purine derivatives

A sustainable strategy for the straightforward preparation of 2H-azirines and highly functionalized NH-aziridines from vinyl azides using a single solvent flow-batch approach

Exploring the possibility of using fluorine-involved non-conjugated electron-withdrawing groups for thermally activated delayed fluorescence emitters by TD-DFT calculation

Total synthesis of decarboxyaltenusin

Other Beilstein-Institut Open Science Activities

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