Synthesis of 1,4-imino-L-lyxitols modified at C-5 and their evaluation as inhibitors of GH38 α-mannosidases

Maroš Bella,
Sergej Šesták,
Ján Moncoľ,
Miroslav Koóš and
Monika Poláková

Full Research Paper
Published 17 Aug 2018

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1. Graphical Abstract
2. Figure 1: Structures of GMIIb inhibitors.
  
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3. Scheme 1: Synthesis of pyrrolidines 2a and 3a.
  
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4. Scheme 2: Synthesis of pyrrolidines 2b,c and 3b,c.
  
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5. Scheme 3: Synthesis of pyrrolidines 4.
  
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6. Scheme 4: Synthesis of pyrrolidines 5.
  
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7. Figure 2: Molecular structure (OLEX2 drawing with adjacent ChemDraw image) of compound 20. Atomic displacemen...
  
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Beilstein J. Org. Chem. 2018, 14, 2156–2162, doi:10.3762/bjoc.14.189

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Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes

Igor B. Krylov,
Stanislav A. Paveliev,
Mikhail A. Syroeshkin,
Alexander A. Korlyukov,
Pavel V. Dorovatovskii,
Yan V. Zubavichus,
Gennady I. Nikishin and
Alexander O. Terent’ev

Full Research Paper
Published 16 Aug 2018

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1. Graphical Abstract
2. Scheme 1: Difunctionalization of double C=C bond with the formation of C–O and C–I bonds.
  
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3. Scheme 2: Iodo-oxyimidation of styrenes 1a–k with preparation of products 3aa–ka, 3ab–db, 3fb, 3hb, and 3kb.
  
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4. Figure 1: Scope of the iodo-oxyimidation of vinylarenes with I₂/PhI(OAc)₂ system. Reaction conditions: vinyla...
  
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5. Figure 2: Molecular structure of 3ca. Atoms are presented as anisotropic displacement parameters (ADP) ellips...
  
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6. Scheme 3: The proposed mechanism of iodo-oxyimidation of styrene (1a) using the NHPI/I₂/PhI(OAc)₂ system with...
  
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7. Figure 3: CV curves of styrene (1a, purple), NHPI (2a, red), I₂ (blue) and PhI(OAc)₂ (green) in 0.1 M n-Bu₄NBF...
  
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8. Scheme 4: Gram-scale synthesis of compound 3aa.
  
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9. Scheme 5: Synthetic utility of the iodo-oxyimides 3aa and 3ab.
  
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Beilstein J. Org. Chem. 2018, 14, 2146–2155, doi:10.3762/bjoc.14.188

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Evaluation of dispersion type metal···π arene interaction in arylbismuth compounds – an experimental and theoretical study

Ana-Maria Preda,
Małgorzata Krasowska,
Lydia Wrobel,
Philipp Kitschke,
Phil C. Andrews,
Jonathan G. MacLellan,
Lutz Mertens,
Marcus Korb,
Tobias Rüffer,
Heinrich Lang,
Alexander A. Auer and
Michael Mehring

Full Research Paper
Published 15 Aug 2018

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1. Graphical Abstract
2. Scheme 1: Triarylbismuth compounds, that serve as examples for the investigation of bismuth···π interactions ...
  
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3. Figure 1: Ball and stick model of a fragment of a) the zig-zag chain of a 1D arrangement of Ph₃Bi (1a). Hydro...
  
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4. Figure 2: Ball and stick model of a fragment of the zig-zag type arrangement of Ph₃Bi (1b) [45], view along the b...
  
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5. Figure 3: Ball and stick model of Ph₃Bi (1c) showing: a) non-centrosymmetric dimers formed via two Bi···π are...
  
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6. Figure 4: Wire and stick representation of (C₆H₄-CH═CH₂-4)₃Bi (2a) showing: a) zig-zag chains of 1D ribbons f...
  
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7. Figure 5: Wire and stick model of (C₆H₄-CH═CH₂-4)₃Bi (2b) showing: a) the formation of 1D ribbons build via t...
  
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8. Figure 6: Molecular structure of (C₆H₄-OMe-4)₃Bi (3) showing: a) Thermal ellipsoids that are set at 50% proba...
  
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9. Figure 7: Wire and stick model of (C₆H₃-t-Bu₂-3,5)₃Bi (4) showing a 3D network build via four C–H_t-_Bu···π (ar...
  
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10. Figure 8: Wire and stick model of (C₆H₃-t-Bu₂-3,5)₂BiCl (5) showing a fragment of the 1D arrangement, view al...
  
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11. Figure 9: Computed interaction potentials of the distance scan for the idealized BiPh₃–benzene complex. E(int...
  
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12. Figure 10: a) The BiPh₃ potential energy curve for idealized interaction structures compared to the interactio...
  
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13. Figure 11: Structures of studied BiPh₃ tetramers extracted from the crystal structure of polymorph 1a. E_tetram...
  
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14. Figure 12: Detailed structures of selected dimers extracted from the crystal structure of polymorph 1a and dis...
  
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15. Figure 13: Structures of studied BiPh₃ tetramers extracted from the crystal structure of polymorph 1b. See Figure 11 fo...
  
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16. Figure 14: Detailed structures of selected dimers extracted from the crystal structure of polymorph 1b and dis...
  
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17. Figure 15: Structures of studied BiPh₃ tetramers extracted from the crystal structure of polymorph 1c. See Figure 11 fo...
  
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18. Figure 16: Detailed structures of selected dimers extracted from the crystal structure of the polymorph 1c and...
  
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19. Figure 17: Distortion energies of monomers (E_prep, blue triangles) and interaction energies of Bi···π and π-st...
  
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Beilstein J. Org. Chem. 2018, 14, 2125–2145, doi:10.3762/bjoc.14.187

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Calix[6]arene-based atropoisomeric pseudo[2]rotaxanes

Carmine Gaeta,
Carmen Talotta and
Placido Neri

Full Research Paper
Published 14 Aug 2018

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1. Graphical Abstract
2. Figure 1: Cartoon representation of the chiral rotaxane of the Goldup group [15,16] (I and I*) and of the chiral pse...
  
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3. Figure 2: Cartoon representation of the rotaxane sequence isomers reported by Leigh [17] (III and IV) and of the ...
  
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4. Figure 3: The possible 8 discrete conformations of a calix[6]arene macrocycle [26].
  
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5. Figure 4: Diastereoisomeric pseudorotaxanes obtained by threading a directional calixarene wheel with directi...
  
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6. Scheme 1: Synthesis of threads 2⁺ and 3⁺. Reagents and conditions: a) hexamethyldisilazane, LiClO₄, 30 min, 6...
  
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7. Figure 5: Possible mechanism for the formation of the two atropoisomeric pseudo[2]rotaxanes 2⁺1^cone and 2⁺1^1,...
  
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8. Figure 6: ¹H NMR spectra (600 MHz, CDCl₃, 298 K) of, from bottom to top: hexahexyloxycalix[6]arene 1; a 1:1 m...
  
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9. Figure 7: DFT-optimized structures of the: (left) 2⁺1^cone and (right) 2⁺1^1,2,3-alt pseudorotaxane atropoisome...
  
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10. Figure 8: The two pseudorotaxane atropoisomers obtained by threading hexahexyloxycalix[6]arene 1 with monosto...
  
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11. Figure 9: The two pseudorotaxane atropoisomers obtained by threading penta-O-methyl-p-tert-butylcalix[5]arene ...
  
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12. Figure 10: ¹H NMR spectra (600 MHz, CDCl₃, 298 K) of, from bottom to top: hexahexyloxycalix[6]arene 1; a 1:1 m...
  
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Beilstein J. Org. Chem. 2018, 14, 2112–2124, doi:10.3762/bjoc.14.186

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Studies towards the synthesis of hyperireflexolide A

G. Hari Mangeswara Rao

Full Research Paper
Published 13 Aug 2018

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1. Graphical Abstract
2. Figure 1: Hyperireflexolide A.
  
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3. Scheme 1: Retrosynthetic strategy.
  
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4. Scheme 2: Hydrolysis of dimethyl ketal 5.
  
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5. Scheme 3: Alkylation of γ-lactone-fused β-ketoester 6.
  
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6. Scheme 4: Synthesis of α,β-unsaturated ketone 11.
  
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Beilstein J. Org. Chem. 2018, 14, 2106–2111, doi:10.3762/bjoc.14.185

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Revisiting ring-degenerate rearrangements of 1-substituted-4-imino-1,2,3-triazoles

James T. Fletcher,
Matthew D. Hanson,
Joseph A. Christensen and
Eric M. Villa

Full Research Paper
Published 10 Aug 2018

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1. Graphical Abstract
2. Figure 1: Conversion of 1-substituted-4-formyltriazole analogs via ring-degenerate rearrangement of 1-substit...
  
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3. Figure 2: ORTEP structure of 2cc’. Thermal ellipsoids shown at 25% probability.
  
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4. Figure 3: ¹H NMR aromatic region of a product mixture compared with reference imine analogs. Singlets appeari...
  
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5. Figure 4: Rearrangement reaction progress of 1a leading to irreversible formation of a colorimetric self-indi...
  
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Beilstein J. Org. Chem. 2018, 14, 2098–2105, doi:10.3762/bjoc.14.184

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Cobalt-catalyzed peri-selective alkoxylation of 1-naphthylamine derivatives

Jiao-Na Han,
Cong Du,
Xinju Zhu,
Zheng-Long Wang,
Yue Zhu,
Zhao-Yang Chu,
Jun-Long Niu and
Mao-Ping Song

Letter
Published 09 Aug 2018

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1. Graphical Abstract
2. Figure 1: Strategies for cobalt-catalyzed alkoxylation.
  
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3. Scheme 1: Reaction scope with respect to N-(naphthalen-1-yl)picolinamide derivatives. Reaction conditions: 1 ...
  
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4. Scheme 2: Reaction scope with respect to alcohols. Reaction conditions: 1a (0.2 mmol), 2 (1.0 mL), CoF₂ (20 m...
  
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5. Scheme 3: Control experiments and mechanistic studies.
  
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6. Scheme 4: Proposed reaction mechanism.
  
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7. Scheme 5: Removal of the directing group.
  
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Beilstein J. Org. Chem. 2018, 14, 2090–2097, doi:10.3762/bjoc.14.183

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D-Fructose-based spiro-fused PHOX ligands: synthesis and application in enantioselective allylic alkylation

Michael R. Imrich,
Jochen Kraft,
Cäcilia Maichle-Mössmer and
Thomas Ziegler

Full Research Paper
Published 08 Aug 2018

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1. Graphical Abstract
2. Figure 1: General structure of PHOX ligands 1 and structures of annulated glucosamine-based PHOX and PyOx lig...
  
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3. Scheme 1: Preparation of 1,2-isopropylidene-protected D-fructose derivatives with different substitution patt...
  
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4. Scheme 2: Activation of 7 to oxocarbenium ion 9 in the Ritter reaction.
  
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5. Scheme 3: Zemplén deacetylation of 10i.
  
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6. Figure 2: Molecular structure of 10j. Ellipsoids are given at the 50% probability level. Grey = carbon, red =...
  
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7. Scheme 4: Benzylation of 10j to give 10b.
  
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8. Scheme 5: Plausible mechanism of the Ritter reaction. For better clarity C-2 is not shown in conformers 9a an...
  
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9. Scheme 6: Neighboring group participation of ester protective groups. For better clarity C-2 is not shown in ...
  
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10. Scheme 7: Pd catalyzed Tsuji–Trost reation. BSA: N,O-bis(trimethylsilyl)acetamide, DMM: dimethyl malonate.
  
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Beilstein J. Org. Chem. 2018, 14, 2082–2089, doi:10.3762/bjoc.14.182

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A switchable [2]rotaxane with two active alkenyl groups

Xiu-Li Zheng,
Rong-Rong Tao,
Rui-Rui Gu,
Wen-Zhi Wang and
Da-Hui Qu

Full Research Paper
Published 08 Aug 2018

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1. Graphical Abstract
2. Scheme 1: Chemical structures and acid-base stimuli responsiveness of target [2]rotaxane R1 and deprotonated ...
  
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3. Scheme 2: Syntheses of key intermediates 5, 8 and target [2]rotaxane R1.
  
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4. Figure 1: Partial ¹H NMR spectra (400 MHz, CDCl₃, 298 K). (a) Compound 5, (b) target [2]rotaxane R1, (c) azid...
  
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5. Figure 2: Partial ¹H NMR spectra (400 MHz, CDCl₃, 298 K). (a) [2]Rotaxane R1, (b) deprotonation by the additi...
  
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6. Figure 3: Partial 2D ROESY NMR spectra (500 MHz, CDCl₃, 298 K). (a) [2]Rotaxane R1, (b) deprotonation with ad...
  
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Beilstein J. Org. Chem. 2018, 14, 2074–2081, doi:10.3762/bjoc.14.181

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Synthesis and supramolecular self-assembly of glutamic acid-based squaramides

Juan V. Alegre-Requena,
Marleen Häring,
Isaac G. Sonsona,
Alex Abramov,
Eugenia Marqués-López,
Raquel P. Herrera and
David Díaz Díaz

Full Research Paper
Published 06 Aug 2018

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1. Graphical Abstract
2. Figure 1: Chemical structures of isosteric gelators 1 and 2 previously studied [33], and squaramide-based analogu...
  
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3. Scheme 1: Synthesis of squaramide-based gelators 3 and 4.
  
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4. Figure 2: Comparison of CGC, gelation time and T_gel values corresponding to six gels made using 3 and 2 [33] as g...
  
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5. Figure 3: DFS measurements for model gels made of 3 in methanol (c = 47 g/L) and ethyl acetate (c = 36 g/L). ...
  
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6. Figure 4: Representative FESEM images of selected xerogels prepared by freeze-drying the corresponding organo...
  
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Beilstein J. Org. Chem. 2018, 14, 2065–2073, doi:10.3762/bjoc.14.180

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Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry

Michael K. Bogdos,
Emmanuel Pinard and
John A. Murphy

Review
Published 03 Aug 2018

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1. Graphical Abstract
2. Figure 1: Depiction of the energy levels of a typical organic molecule and the photophysical processes it can...
  
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3. Figure 2: General catalytic cycle of a photocatalyst in a photoredox organocatalysed reaction. [cat] – photoc...
  
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4. Figure 3: Structures and names of the most common photocatalysts encountered in the reviewed literature.
  
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5. Figure 4: General example of a reductive quenching catalytic cycle. [cat] – photocatalyst, [cat]* – photocata...
  
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6. Figure 5: General example of an oxidative quenching catalytic cycle. [cat] – photocatalyst, [cat]* – photocat...
  
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7. Scheme 1: Oxidative coupling of aldehydes and amines to amides using acridinium salt photocatalysis.
  
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8. Figure 6: Biologically active molecules containing a benzamide linkage.
  
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9. Scheme 2: The photocatalytic reduction of amino acids to produce the corresponding free or protected amines.
  
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10. Scheme 3: The organocatalysed photoredox base-mediated oxidation of thiols to disulfides.
  
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11. Scheme 4: C-Terminal modification of peptides and proteins using organophotoredox catalysis.
  
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12. Scheme 5: The reduction and aryl coupling of aryl halides using a doubly excited photocatalyst (PDI).
  
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13. Figure 7: Mechanism for the coupling of aryl halides using PDI, which is excited sequentially by two photons.
  
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14. Scheme 6: The arylation of five-membered heteroarenes using arenediazonium salts under organophotoredox condi...
  
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15. Scheme 7: The C–H (hetero)arylation of five-membered heterocycles under Eosin Y photocatalysis.
  
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16. Scheme 8: The C–H sulfurisation of imidazoheterocycles using Eosin B-catalyzed photochemical methods.
  
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17. Scheme 9: The introduction of the thiocyanate group using Eosin Y photocatalysis.
  
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18. Scheme 10: Sulfonamidation of pyrroles using oxygen as the terminal oxidant.
  
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19. Scheme 11: DDQ-catalysed C–H amination of arenes and heteroarenes.
  
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20. Scheme 12: Photoredox-promoted radical Michael addition reactions of allylic or benzylic carbons.
  
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21. Figure 8: Proposed mechanistic rationale for the observed chemoselectivities.
  
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22. Scheme 13: The photocatalytic manipulation of C–H bonds adjacent to amine groups.
  
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23. Scheme 14: The perylene-catalysed organophotoredox tandem difluoromethylation–acetamidation of styrene-type al...
  
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24. Figure 9: Examples of biologically active molecules containing highly functionalised five membered heterocycl...
  
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25. Scheme 15: The [3 + 2]-cycloaddition leading to the formation of pyrroles, through the reaction of 2H-azirines...
  
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26. Figure 10: Proposed intermediate that determines the regioselectivity of the reaction.
  
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27. Figure 11: Comparison of possible pathways of reaction and various intermediates involved.
  
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28. Scheme 16: The acridinium salt-catalysed formation of oxazoles from aldehydes and 2H-azirines.
  
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29. Scheme 17: The synthesis of oxazolines and thiazolines from amides and thioamides using organocatalysed photor...
  
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30. Figure 12: Biologically active molecules on the market containing 1,3,4-oxadiazole moieties.
  
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31. Scheme 18: The synthesis of 1,3,4-oxadiazoles from aldehyde semicarbazones using Eosin Y organophotocatalysis.
  
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32. Scheme 19: The dimerization of primary thioamides to 1,2,4-thiadiazoles catalysed by the presence of Eosin Y a...
  
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33. Scheme 20: The radical cycloaddition of o-methylthioarenediazonium salts and substituted alkynes towards the f...
  
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34. Scheme 21: The dehydrogenative cascade reaction for the synthesis of 5,6-benzofused heterocyclic systems.
  
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35. Figure 13: Trifluoromethylated version of compounds which have known biological activities.
  
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36. Scheme 22: Eosin Y-catalysed photoredox formation of 3-substituted benzimidazoles.
  
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37. Scheme 23: Oxidation of dihydropyrimidines by atmospheric oxygen using photoredox catalysis.
  
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38. Scheme 24: Photoredox-organocatalysed transformation of 2-substituted phenolic imines to benzoxazoles.
  
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39. Scheme 25: Visible light-driven oxidative annulation of arylamidines.
  
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40. Scheme 26: Methylene blue-photocatalysed direct C–H trifluoromethylation of heterocycles.
  
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41. Scheme 27: Photoredox hydrotrifluoromethylation of terminal alkenes and alkynes.
  
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42. Scheme 28: Trifluoromethylation and perfluoroalkylation of aromatics and heteroaromatics.
  
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43. Scheme 29: The cooperative asymmetric and photoredox catalysis towards the functionalisation of α-amino sp³ C–...
  
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44. Scheme 30: Organophotoredox-catalysed direct C–H amidation of aromatics.
  
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45. Scheme 31: Direct C–H alkylation of heterocycles using BF₃K salts. CFL – compact fluorescent lamp.
  
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46. Figure 14: The modification of camptothecin, demonstrating the use of the Molander protocol in LSF.
  
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47. Scheme 32: Direct C–H amination of aromatics using acridinium salts.
  
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48. Scheme 33: Photoredox-catalysed nucleophilic aromatic substitution of nucleophiles onto methoxybenzene derivat...
  
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49. Scheme 34: The direct C–H cyanation of aromatics with a focus on its use for LSF.
  
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Beilstein J. Org. Chem. 2018, 14, 2035–2064, doi:10.3762/bjoc.14.179

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Coordination-driven self-assembly vs dynamic covalent chemistry: versatile methods for the synthesis of molecular metallarectangles

Li-Li Ma,
Jia-Qin Han,
Wei-Guo Jia and
Ying-Feng Han

Full Research Paper
Published 03 Aug 2018

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1. Graphical Abstract
2. Scheme 1: Synthesis of half-sandwich rhodium metallarectangles via three different methods. Method A: coordin...
  
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3. Figure 1: Partial ¹H NMR spectra (400 MHz, DMSO-d₆, ppm) of (a) L1; (b) the sample of metallarectagle 3a obta...
  
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4. Figure 2: Partial ¹H NMR spectra (400 MHz, DMSO-d₆, ppm) of (a) L2; (b) a sample of metallarectangle 3b obtai...
  
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5. Figure 3: Calculated (bottom) and experimental (top) ESI-MS spectra of the tetracationic half-sandwich rhodiu...
  
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6. Figure 4: Optimized structures of the charged metallarectangles 3a (top) and 3b (bottom), optimized with the ...
  
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Beilstein J. Org. Chem. 2018, 14, 2027–2034, doi:10.3762/bjoc.14.178

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Functionalization of graphene: does the organic chemistry matter?

Artur Kasprzak,
Agnieszka Zuchowska and
Magdalena Poplawska

Review
Published 02 Aug 2018

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1. Graphical Abstract
2. Figure 1: Partial structure [7,8] of the (a) graphene oxide (GO) and (b) reduced graphene oxide (RGO).
  
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3. Figure 2: Mechanism of the amidation/esterification-type reactions with the GO/RGO using carbodiimide and N-h...
  
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4. Figure 3: Mechanism of the Steglich esterification with the GO/RGO: (a) acid–base reaction of the carboxyl gr...
  
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5. Figure 4: Mechanism of the epoxide ring opening reaction with the GO/RGO.
  
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6. Figure 5: Generation of the free amine (nucleophile) from the corresponding amine hydrohalide using an acid–b...
  
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7. Figure 6: Mechanism of amidation/esterification-type reactions with the GO/RGO using 1,1’-carbonyldiimidazole...
  
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8. Figure 7: Mechanism of the covalent functionalization of graphene-family material applying diazonium salts ch...
  
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Beilstein J. Org. Chem. 2018, 14, 2018–2026, doi:10.3762/bjoc.14.177

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Cobalt-catalyzed nucleophilic addition of the allylic C(sp³)–H bond of simple alkenes to ketones

Tsuyoshi Mita,
Masashi Uchiyama,
Kenichi Michigami and
Yoshihiro Sato

Letter
Published 02 Aug 2018

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1. Graphical Abstract
2. Figure 1: Precedent examples of catalytic allylic C(sp³)–H additions to carbonyl electrophiles.
  
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3. Figure 2: Substrate scope for acetophenone derivatives. ^aPreparative scale synthesis using 1 mmol of 2a.
  
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4. Figure 3: Substrate scope for α-olefins.
  
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5. Figure 4: A possible catalytic cycle.
  
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Beilstein J. Org. Chem. 2018, 14, 2012–2017, doi:10.3762/bjoc.14.176

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Chiral bisoxazoline ligands designed to stabilize bimetallic complexes

Deepankar Das,
Rudrajit Mal,
Nisha Mittal,
Zhengbo Zhu,
Thomas J. Emge and
Daniel Seidel

Full Research Paper
Published 01 Aug 2018

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1. Graphical Abstract
2. Figure 1: Examples of chiral bimetallic complexes utilized in asymmetric catalysis.
  
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3. Figure 2: Previously reported bisoxazoline ligands capable of stabilizing bimetallic complexes.
  
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4. Scheme 1: Synthesis of naphthyridine–bisoxazoline ligand 16-H₂.
  
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5. Figure 3: Thermal ellipsoid plot (50% probability) of the molecular structure of 16·Ni₂(OAc)₂. Hydrogen and s...
  
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6. Scheme 2: Synthesis of naphthyridine–bisoxazoline ligand 22-H₂.
  
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7. Scheme 3: Synthesis of pyrazole–bisoxazoline ligand 25-H₃.
  
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8. Figure 4: Thermal ellipsoid plot (50% probability) of the molecular structure of 25·Ni₂(OAc). Hydrogen and so...
  
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9. Scheme 4: Synthesis of pyrazole–bisoxazoline ligand 30-H₃.
  
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10. Figure 5: Thermal ellipsoid plot (50% probability) of the molecular structure of 30·Pd₂Br. Hydrogen and solva...
  
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11. Scheme 5: Synthesis of pyridazine–bisoxazoline ligand 32-H₂.
  
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12. Figure 6: Thermal ellipsoid plot (50% probability) of the molecular structure of 32·Zn₂Cl₂. Hydrogen and solv...
  
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13. Scheme 6: Synthesis of phenol–bisoxazoline ligand 34-H₃.
  
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Beilstein J. Org. Chem. 2018, 14, 2002–2011, doi:10.3762/bjoc.14.175

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A self-assembled photoresponsive gel consisting of chiral nanofibers

Lei Zou,
Dan Han,
Zhiyi Yuan,
Dongdong Chang and
Xiang Ma

Letter
Published 01 Aug 2018

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1. Graphical Abstract
2. Scheme 1: The preparation of compound 3.
  
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3. Figure 1: The chemical structure and the schematic representation of compound 3 as well as the proposed assem...
  
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4. Figure 2: UV–vis absorbance spectra of a) compound 3 and b) irradiated by a light source of 365 nm and c) the...
  
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5. Figure 3: CD spectrum of compound 3 in solutions of a) benzene, toluene, p-xylene, chloroform, tetrachloromet...
  
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6. Figure 4: SEM images of the microstructure a) obtained by the self-assembled compound 3 in CHCl₃ on the surfa...
  
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7. Figure 5: a) The gel-to-sol transformation of the samples via different routes. b) Dynamic frequency sweep of...
  
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Beilstein J. Org. Chem. 2018, 14, 1994–2001, doi:10.3762/bjoc.14.174

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Synthesis of new p-tert-butylcalix[4]arene-based polyammonium triazolyl amphiphiles and their binding with nucleoside phosphates

Vladimir A. Burilov,
Guzaliya A. Fatikhova,
Mariya N. Dokuchaeva,
Ramil I. Nugmanov,
Diana A. Mironova,
Pavel V. Dorovatovskii,
Victor N. Khrustalev,
Svetlana E. Solovieva and
Igor S. Antipin

Full Research Paper
Published 31 Jul 2018

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1. Graphical Abstract
2. Scheme 1: The general structure of triazolylcalix[4]arene derivatives.
  
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3. Scheme 2: Synthesis of di- (4a,b) and tetraazido (8a,b) calix[4]arene derivatives. Conditions: Ia: AlkBr, K₂CO...
  
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4. Figure 1: Molecular structure of 8a (50% ellipsoids). The dashed line indicates the alternative position of t...
  
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5. Scheme 3: Synthesis of polyammonium macrocycles 10a,b and 12a,b.
  
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6. Figure 2: 2D NOESY H¹-H¹ NMR spectra of 10b in DMSO-d₆.
  
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7. Figure 3: The optical response (OR) of the calixarene/EY systems toward adenosine phosphates. Concentration (...
  
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8. Figure 4: Supramolecular binding motif of diphosphate (a) and triphosphate (b) groups of nucleotides with the...
  
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9. Figure 5: UV spectra of EY (1), 10b–EY (2), and 10b–EY in the presence of 0.005 (3), 0.05 (4), 0.5 (5) and 2 ...
  
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10. Scheme 4: Structure of AEPDA and the corresponding AEPCDA–10b polydiacetylene vesicle.
  
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11. Figure 6: UV spectra of the AEPCDA polydiacetylene vesicles in the presence of different amounts of 10b; conc...
  
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12. Figure 7: Photographs of a portion of a 96-well plate containing AEPCDA–10b polydiacetylene vesicles in the a...
  
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Beilstein J. Org. Chem. 2018, 14, 1980–1993, doi:10.3762/bjoc.14.173

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Cationic cobalt-catalyzed [1,3]-rearrangement of N-alkoxycarbonyloxyanilines

Itaru Nakamura,
Mao Owada,
Takeru Jo and
Masahiro Terada

Full Research Paper
Published 31 Jul 2018

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1. Graphical Abstract
2. Scheme 1: ortho-Aminophenol derivatives.
  
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3. Scheme 2: Rearrangement of N-acyloxyanilines.
  
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4. Scheme 3: Mechanistic studies, reported in [13].
  
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5. Scheme 4: Competitive experiments, reported in [13].
  
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6. Scheme 5: Mechanism for rearrangement to the para-position.
  
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Beilstein J. Org. Chem. 2018, 14, 1972–1979, doi:10.3762/bjoc.14.172

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Rational design of boron-dipyrromethene (BODIPY) reporter dyes for cucurbit[7]uril

Mohammad A. Alnajjar,
Jürgen Bartelmeß,
Robert Hein,
Pichandi Ashokkumar,
Mohamed Nilam,
Werner M. Nau,
Knut Rurack and
Andreas Hennig

Full Research Paper
Published 30 Jul 2018

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1. Graphical Abstract
2. Figure 1: a) The “anchor group” approach for a rational design of CB–dye pairs involving a thermodynamic cycl...
  
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3. Scheme 1: Synthesis of BODIPY derivatives.
  
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4. Figure 2: a) Normalized absorption (solid line) and normalized fluorescence emission spectrum (dotted line) o...
  
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5. Figure 3: a) Fluorescence spectral changes (λ_exc = 470 nm) upon addition of CB7 to 50 nM 1 in 10 mM citrate b...
  
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6. Figure 4: Fluorescence pH titration of 2 and the respective complex (in presence of 3 mM CB7) in 30% (v/v) AC...
  
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7. Figure 5: Fluorescence displacement titrations (λ_ex = 470 nm, λ_em = 510 nm). a) 5 µM 2 and 2.5 µM CB7 with cy...
  
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8. Figure 6: FCS autocorrelation curves obtained with 10 nM 2 in the absence (red fitted line) and presence (blu...
  
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9. Figure 7: Fluorescence microscopy images of 1 mg/mL polymer microspheres a) with or b) without surface-bound ...
  
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Beilstein J. Org. Chem. 2018, 14, 1961–1971, doi:10.3762/bjoc.14.171

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Synthesis and characterization of π–extended “earring” subporphyrins

Haiyan Guan,
Mingbo Zhou,
Bangshao Yin,
Ling Xu and
Jianxin Song

Letter
Published 30 Jul 2018

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1. Graphical Abstract
2. Scheme 1: Synthesis of “earring” subporphyrin and its Pd complex. Synthetic procedure: (i) Diboryltripyrrane ...
  
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3. Figure 1: Partial ¹H NMR spectrum of 3.
  
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4. Figure 2: X-ray crystal structures of 3: a) top view; b) side view. Thermal ellipsoids are drawn at the 50% p...
  
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5. Figure 3: Partial ¹H NMR spectrum of 3Pd.
  
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6. Figure 4: X-ray crystal structures of 3Pd: a) top view; b) side view. Thermal ellipsoids are at the 30% proba...
  
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7. Figure 5: UV–vis/NIR spectra of 3 and 3Pd.
  
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Beilstein J. Org. Chem. 2018, 14, 1956–1960, doi:10.3762/bjoc.14.170

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Artificial bioconjugates with naturally occurring linkages: the use of phosphodiester

Takao Shoji,
Hiroki Fukutomi,
Yohei Okada and
Kazuhiro Chiba

Full Research Paper
Published 27 Jul 2018

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2. Figure 1: Schematic illustration of possible support-assisted methods.
  
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3. Figure 2: Expected reactivity of 5’- and 3’-terminus for the activation.
  
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4. Scheme 1: Competition experiment between alcohol and carboxylic acid. Reagents and conditions: (i) 4-phenylbu...
  
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5. Scheme 2: Conjugation between the 5’-activated supported trinucleotide 2 and the tripeptide 3. Reagents and c...
  
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6. Figure 3: HPLC spectra of the crude protected bioconjugate 4 and the crude deprotected bioconjugate 5.
  
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7. Scheme 3: 5’-Phosphitylation of supported decanucleotide 13. Reagents and conditions: 2-cyanoethyl-N,N,N',N'-...
  
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8. Scheme 4: Conjugation between 5’-activated supported decanucleotide 14 and supported pentapeptide 7. Reagents...
  
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9. Figure 4: HPLC spectra of the crude protected bioconjugate 15 and the deprotected bioconjugate 16.
  
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Beilstein J. Org. Chem. 2018, 14, 1946–1955, doi:10.3762/bjoc.14.169

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Recent advances in materials for organic light emitting diodes

Eli Zysman-Colman

Editorial
Published 27 Jul 2018

Beilstein J. Org. Chem. 2018, 14, 1944–1945, doi:10.3762/bjoc.14.168

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An amphiphilic pseudo[1]catenane: neutral guest-induced clouding point change

Tomoki Ogoshi,
Tomohiro Akutsu and
Tada-aki Yamagishi

Full Research Paper
Published 26 Jul 2018

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2. Figure 1: Chemical structures of (a) tri(ethylene oxide)-substituted pillar[n]arenes (1, n = 5; 2, n = 6), (b...
  
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3. Figure 2: ¹H NMR spectra of (a) model compound 4 (2 mM at 25 °C in CDCl₃), (b) 3 (2 mM at 25 °C in CDCl₃), (c...
  
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4. Figure 3: Temperature dependence of light transmittance at 650 nm of an aqueous solution of (a) 3 (2 mM) upon...
  
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5. Figure 4: Photographs of (a) 3 and (c) a mixture of 3 (2 mM) and 1,4-dicyanobutane (20 mM) in aqueous media a...
  
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6. Scheme 1: Synthesis of the bicyclic compound 3.
  
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Beilstein J. Org. Chem. 2018, 14, 1937–1943, doi:10.3762/bjoc.14.167

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Assessing the possibilities of designing a unified multistep continuous flow synthesis platform

Mrityunjay K. Sharma,
Roopashri B. Acharya,
Chinmay A. Shukla and
Amol A. Kulkarni

Review
Published 26 Jul 2018

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1. Graphical Abstract
2. Figure 1: Key features of different approaches for unified multistep synthesis platform.
  
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3. Figure 2: Schematic representation of a unified platform for the flow synthesis (P1–P14 pumps, PBR packed bed...
  
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4. Figure 3: Layout of a unified synthesis platform (including all the component) for multiple drug molecules (a...
  
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5. Figure 4: Layout for synthesis of 4 molecules on a single platform (approach 2).
  
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6. Scheme 1: The overall process for the synthesis of diphenhydramine hydrochloride.
  
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7. Figure 5: Approach 3 for a unified platform for multistep synthesis. M1–M9 = mixers, R1–R4 = tubular reactors...
  
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Beilstein J. Org. Chem. 2018, 14, 1917–1936, doi:10.3762/bjoc.14.166

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A pyridinium/anilinium [2]catenane that operates as an acid–base driven optical switch

Sarah J. Vella and
Stephen J. Loeb

Full Research Paper
Published 25 Jul 2018

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2. Figure 1: Two [2]rotaxane molecular shuttles with both bis(pyridinium)ethane and benzylanilinium recognition ...
  
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3. Figure 2: A [3]catenane containing two identical bis(pyridinium)ethane recognition sites on a large macrocycl...
  
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4. Scheme 1: Step-wise synthesis of [2]catenane [8DB24C8]⁶⁺ containing benzylanilinium and bis(pyridinium)ethane...
  
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5. Figure 3: ¹H NMR spectrum of [2]catenane [8DB24C8]⁶⁺ (500 MHz, 298 K, CD₂Cl₂) showing the assigned proton che...
  
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6. Figure 4: a) The [2]catenane [8DB24C8]⁶⁺ can be protonated to yield [8-HDB24C8]⁷⁺ in two different co-conform...
  
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7. Figure 5: UV–visible spectra of [8DB24C8]⁶⁺ (orange trace) and [8-HDB24C8]⁷⁺ (black trace) in CH₃CN solution ...
  
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