Studies towards the synthesis of hyperireflexolide A

G. Hari Mangeswara Rao

Full Research Paper
Published 13 Aug 2018

PDF
Album
1. Graphical Abstract
2. Figure 1: Hyperireflexolide A.
  
  Jump to Figure 1
3. Scheme 1: Retrosynthetic strategy.
  
  Jump to Scheme 1
4. Scheme 2: Hydrolysis of dimethyl ketal 5.
  
  Jump to Scheme 2
5. Scheme 3: Alkylation of γ-lactone-fused β-ketoester 6.
  
  Jump to Scheme 3
6. Scheme 4: Synthesis of α,β-unsaturated ketone 11.
  
  Jump to Scheme 4
Supp. Info

Beilstein J. Org. Chem. 2018, 14, 2106–2111, doi:10.3762/bjoc.14.185

Full Text

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

PDF
Album
1. Graphical Abstract
2. Figure 1: Conversion of 1-substituted-4-formyltriazole analogs via ring-degenerate rearrangement of 1-substit...
  
  Jump to Figure 1
3. Figure 2: ORTEP structure of 2cc’. Thermal ellipsoids shown at 25% probability.
  
  Jump to Figure 2
4. Figure 3: ¹H NMR aromatic region of a product mixture compared with reference imine analogs. Singlets appeari...
  
  Jump to Figure 3
5. Figure 4: Rearrangement reaction progress of 1a leading to irreversible formation of a colorimetric self-indi...
  
  Jump to Figure 4
Supp. Info

Beilstein J. Org. Chem. 2018, 14, 2098–2105, doi:10.3762/bjoc.14.184

Full Text

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

PDF
Album
1. Graphical Abstract
2. Figure 1: Strategies for cobalt-catalyzed alkoxylation.
  
  Jump to Figure 1
3. Scheme 1: Reaction scope with respect to N-(naphthalen-1-yl)picolinamide derivatives. Reaction conditions: 1 ...
  
  Jump to Scheme 1
4. Scheme 2: Reaction scope with respect to alcohols. Reaction conditions: 1a (0.2 mmol), 2 (1.0 mL), CoF₂ (20 m...
  
  Jump to Scheme 2
5. Scheme 3: Control experiments and mechanistic studies.
  
  Jump to Scheme 3
6. Scheme 4: Proposed reaction mechanism.
  
  Jump to Scheme 4
7. Scheme 5: Removal of the directing group.
  
  Jump to Scheme 5
Supp. Info

Beilstein J. Org. Chem. 2018, 14, 2090–2097, doi:10.3762/bjoc.14.183

Full Text

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

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

Beilstein J. Org. Chem. 2018, 14, 2082–2089, doi:10.3762/bjoc.14.182

Full Text

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

PDF
Album
1. Graphical Abstract
2. Scheme 1: Chemical structures and acid-base stimuli responsiveness of target [2]rotaxane R1 and deprotonated ...
  
  Jump to Scheme 1
3. Scheme 2: Syntheses of key intermediates 5, 8 and target [2]rotaxane R1.
  
  Jump to Scheme 2
4. Figure 1: Partial ¹H NMR spectra (400 MHz, CDCl₃, 298 K). (a) Compound 5, (b) target [2]rotaxane R1, (c) azid...
  
  Jump to Figure 1
5. Figure 2: Partial ¹H NMR spectra (400 MHz, CDCl₃, 298 K). (a) [2]Rotaxane R1, (b) deprotonation by the additi...
  
  Jump to Figure 2
6. Figure 3: Partial 2D ROESY NMR spectra (500 MHz, CDCl₃, 298 K). (a) [2]Rotaxane R1, (b) deprotonation with ad...
  
  Jump to Figure 3
Supp. Info

Beilstein J. Org. Chem. 2018, 14, 2074–2081, doi:10.3762/bjoc.14.181

Full Text

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

PDF
Album
1. Graphical Abstract
2. Figure 1: Chemical structures of isosteric gelators 1 and 2 previously studied [33], and squaramide-based analogu...
  
  Jump to Figure 1
3. Scheme 1: Synthesis of squaramide-based gelators 3 and 4.
  
  Jump to Scheme 1
4. Figure 2: Comparison of CGC, gelation time and T_gel values corresponding to six gels made using 3 and 2 [33] as g...
  
  Jump to Figure 2
5. Figure 3: DFS measurements for model gels made of 3 in methanol (c = 47 g/L) and ethyl acetate (c = 36 g/L). ...
  
  Jump to Figure 3
6. Figure 4: Representative FESEM images of selected xerogels prepared by freeze-drying the corresponding organo...
  
  Jump to Figure 4
Supp. Info

Beilstein J. Org. Chem. 2018, 14, 2065–2073, doi:10.3762/bjoc.14.180

Full Text

Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry

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

Review
Published 03 Aug 2018

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

Beilstein J. Org. Chem. 2018, 14, 2035–2064, doi:10.3762/bjoc.14.179

Full Text

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

PDF
Album
1. Graphical Abstract
2. Scheme 1: Synthesis of half-sandwich rhodium metallarectangles via three different methods. Method A: coordin...
  
  Jump to Scheme 1
3. Figure 1: Partial ¹H NMR spectra (400 MHz, DMSO-d₆, ppm) of (a) L1; (b) the sample of metallarectagle 3a obta...
  
  Jump to Figure 1
4. Figure 2: Partial ¹H NMR spectra (400 MHz, DMSO-d₆, ppm) of (a) L2; (b) a sample of metallarectangle 3b obtai...
  
  Jump to Figure 2
5. Figure 3: Calculated (bottom) and experimental (top) ESI-MS spectra of the tetracationic half-sandwich rhodiu...
  
  Jump to Figure 3
6. Figure 4: Optimized structures of the charged metallarectangles 3a (top) and 3b (bottom), optimized with the ...
  
  Jump to Figure 4

Beilstein J. Org. Chem. 2018, 14, 2027–2034, doi:10.3762/bjoc.14.178

Full Text

Functionalization of graphene: does the organic chemistry matter?

Artur Kasprzak,
Agnieszka Zuchowska and
Magdalena Poplawska

Review
Published 02 Aug 2018

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

Beilstein J. Org. Chem. 2018, 14, 2018–2026, doi:10.3762/bjoc.14.177

Full Text

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

PDF
Album
1. Graphical Abstract
2. Figure 1: Precedent examples of catalytic allylic C(sp³)–H additions to carbonyl electrophiles.
  
  Jump to Figure 1
3. Figure 2: Substrate scope for acetophenone derivatives. ^aPreparative scale synthesis using 1 mmol of 2a.
  
  Jump to Figure 2
4. Figure 3: Substrate scope for α-olefins.
  
  Jump to Figure 3
5. Figure 4: A possible catalytic cycle.
  
  Jump to Figure 4
Supp. Info

Beilstein J. Org. Chem. 2018, 14, 2012–2017, doi:10.3762/bjoc.14.176

Full Text

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

PDF
Album
1. Graphical Abstract
2. Figure 1: Examples of chiral bimetallic complexes utilized in asymmetric catalysis.
  
  Jump to Figure 1
3. Figure 2: Previously reported bisoxazoline ligands capable of stabilizing bimetallic complexes.
  
  Jump to Figure 2
4. Scheme 1: Synthesis of naphthyridine–bisoxazoline ligand 16-H₂.
  
  Jump to Scheme 1
5. Figure 3: Thermal ellipsoid plot (50% probability) of the molecular structure of 16·Ni₂(OAc)₂. Hydrogen and s...
  
  Jump to Figure 3
6. Scheme 2: Synthesis of naphthyridine–bisoxazoline ligand 22-H₂.
  
  Jump to Scheme 2
7. Scheme 3: Synthesis of pyrazole–bisoxazoline ligand 25-H₃.
  
  Jump to Scheme 3
8. Figure 4: Thermal ellipsoid plot (50% probability) of the molecular structure of 25·Ni₂(OAc). Hydrogen and so...
  
  Jump to Figure 4
9. Scheme 4: Synthesis of pyrazole–bisoxazoline ligand 30-H₃.
  
  Jump to Scheme 4
10. Figure 5: Thermal ellipsoid plot (50% probability) of the molecular structure of 30·Pd₂Br. Hydrogen and solva...
  
  Jump to Figure 5
11. Scheme 5: Synthesis of pyridazine–bisoxazoline ligand 32-H₂.
  
  Jump to Scheme 5
12. Figure 6: Thermal ellipsoid plot (50% probability) of the molecular structure of 32·Zn₂Cl₂. Hydrogen and solv...
  
  Jump to Figure 6
13. Scheme 6: Synthesis of phenol–bisoxazoline ligand 34-H₃.
  
  Jump to Scheme 6
Supp. Info

Beilstein J. Org. Chem. 2018, 14, 2002–2011, doi:10.3762/bjoc.14.175

Full Text

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

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

Beilstein J. Org. Chem. 2018, 14, 1994–2001, doi:10.3762/bjoc.14.174

Full Text

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

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

Beilstein J. Org. Chem. 2018, 14, 1980–1993, doi:10.3762/bjoc.14.173

Full Text

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

PDF
Album
1. Graphical Abstract
2. Scheme 1: ortho-Aminophenol derivatives.
  
  Jump to Scheme 1
3. Scheme 2: Rearrangement of N-acyloxyanilines.
  
  Jump to Scheme 2
4. Scheme 3: Mechanistic studies, reported in [13].
  
  Jump to Scheme 3
5. Scheme 4: Competitive experiments, reported in [13].
  
  Jump to Scheme 4
6. Scheme 5: Mechanism for rearrangement to the para-position.
  
  Jump to Scheme 5
Supp. Info

Beilstein J. Org. Chem. 2018, 14, 1972–1979, doi:10.3762/bjoc.14.172

Full Text

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

PDF
Album
1. Graphical Abstract
2. Figure 1: a) The “anchor group” approach for a rational design of CB–dye pairs involving a thermodynamic cycl...
  
  Jump to Figure 1
3. Scheme 1: Synthesis of BODIPY derivatives.
  
  Jump to Scheme 1
4. Figure 2: a) Normalized absorption (solid line) and normalized fluorescence emission spectrum (dotted line) o...
  
  Jump to Figure 2
5. Figure 3: a) Fluorescence spectral changes (λ_exc = 470 nm) upon addition of CB7 to 50 nM 1 in 10 mM citrate b...
  
  Jump to Figure 3
6. Figure 4: Fluorescence pH titration of 2 and the respective complex (in presence of 3 mM CB7) in 30% (v/v) AC...
  
  Jump to Figure 4
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...
  
  Jump to Figure 5
8. Figure 6: FCS autocorrelation curves obtained with 10 nM 2 in the absence (red fitted line) and presence (blu...
  
  Jump to Figure 6
9. Figure 7: Fluorescence microscopy images of 1 mg/mL polymer microspheres a) with or b) without surface-bound ...
  
  Jump to Figure 7
Supp. Info

Beilstein J. Org. Chem. 2018, 14, 1961–1971, doi:10.3762/bjoc.14.171

Full Text

Synthesis and characterization of π–extended “earring” subporphyrins

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

Letter
Published 30 Jul 2018

PDF
Album
1. Graphical Abstract
2. Scheme 1: Synthesis of “earring” subporphyrin and its Pd complex. Synthetic procedure: (i) Diboryltripyrrane ...
  
  Jump to Scheme 1
3. Figure 1: Partial ¹H NMR spectrum of 3.
  
  Jump to Figure 1
4. Figure 2: X-ray crystal structures of 3: a) top view; b) side view. Thermal ellipsoids are drawn at the 50% p...
  
  Jump to Figure 2
5. Figure 3: Partial ¹H NMR spectrum of 3Pd.
  
  Jump to Figure 3
6. Figure 4: X-ray crystal structures of 3Pd: a) top view; b) side view. Thermal ellipsoids are at the 30% proba...
  
  Jump to Figure 4
7. Figure 5: UV–vis/NIR spectra of 3 and 3Pd.
  
  Jump to Figure 5
Supp. Info

Beilstein J. Org. Chem. 2018, 14, 1956–1960, doi:10.3762/bjoc.14.170

Full Text

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

PDF
Album
1. Graphical Abstract
2. Figure 1: Schematic illustration of possible support-assisted methods.
  
  Jump to Figure 1
3. Figure 2: Expected reactivity of 5’- and 3’-terminus for the activation.
  
  Jump to Figure 2
4. Scheme 1: Competition experiment between alcohol and carboxylic acid. Reagents and conditions: (i) 4-phenylbu...
  
  Jump to Scheme 1
5. Scheme 2: Conjugation between the 5’-activated supported trinucleotide 2 and the tripeptide 3. Reagents and c...
  
  Jump to Scheme 2
6. Figure 3: HPLC spectra of the crude protected bioconjugate 4 and the crude deprotected bioconjugate 5.
  
  Jump to Figure 3
7. Scheme 3: 5’-Phosphitylation of supported decanucleotide 13. Reagents and conditions: 2-cyanoethyl-N,N,N',N'-...
  
  Jump to Scheme 3
8. Scheme 4: Conjugation between 5’-activated supported decanucleotide 14 and supported pentapeptide 7. Reagents...
  
  Jump to Scheme 4
9. Figure 4: HPLC spectra of the crude protected bioconjugate 15 and the deprotected bioconjugate 16.
  
  Jump to Figure 4
Supp. Info

Beilstein J. Org. Chem. 2018, 14, 1946–1955, doi:10.3762/bjoc.14.169

Full Text

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

Full Text

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

PDF
Album
1. Graphical Abstract
2. Figure 1: Chemical structures of (a) tri(ethylene oxide)-substituted pillar[n]arenes (1, n = 5; 2, n = 6), (b...
  
  Jump to Figure 1
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...
  
  Jump to Figure 2
4. Figure 3: Temperature dependence of light transmittance at 650 nm of an aqueous solution of (a) 3 (2 mM) upon...
  
  Jump to Figure 3
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...
  
  Jump to Figure 4
6. Scheme 1: Synthesis of the bicyclic compound 3.
  
  Jump to Scheme 1
Supp. Info

Beilstein J. Org. Chem. 2018, 14, 1937–1943, doi:10.3762/bjoc.14.167

Full Text

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

PDF
Album
1. Graphical Abstract
2. Figure 1: Key features of different approaches for unified multistep synthesis platform.
  
  Jump to Figure 1
3. Figure 2: Schematic representation of a unified platform for the flow synthesis (P1–P14 pumps, PBR packed bed...
  
  Jump to Figure 2
4. Figure 3: Layout of a unified synthesis platform (including all the component) for multiple drug molecules (a...
  
  Jump to Figure 3
5. Figure 4: Layout for synthesis of 4 molecules on a single platform (approach 2).
  
  Jump to Figure 4
6. Scheme 1: The overall process for the synthesis of diphenhydramine hydrochloride.
  
  Jump to Scheme 1
7. Figure 5: Approach 3 for a unified platform for multistep synthesis. M1–M9 = mixers, R1–R4 = tubular reactors...
  
  Jump to Figure 5

Beilstein J. Org. Chem. 2018, 14, 1917–1936, doi:10.3762/bjoc.14.166

Full Text

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

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

Beilstein J. Org. Chem. 2018, 14, 1908–1916, doi:10.3762/bjoc.14.165

Full Text

Asymmetric Michael addition reactions catalyzed by calix[4]thiourea cyclohexanediamine derivatives

Zheng-Yi Li,
Hong-Xiao Tong,
Yuan Chen,
Hong-Kui Su,
Tangxin Xiao,
Xiao-Qiang Sun and
Leyong Wang

Full Research Paper
Published 25 Jul 2018

PDF
Album
1. Graphical Abstract
2. Scheme 1: Catalysts synthesized and screened in this study.
  
  Jump to Scheme 1
3. Scheme 2: Synthetic routes for organocatalysts 1–4.
  
  Jump to Scheme 2
4. Figure 1: Asymmetric Michael addition of acetylacetone with different nitroolefins catalyzed by organocatalys...
  
  Jump to Figure 1
5. Scheme 3: Possible proposed reaction mechanism.
  
  Jump to Scheme 3
Supp. Info

Beilstein J. Org. Chem. 2018, 14, 1901–1907, doi:10.3762/bjoc.14.164

Full Text

Diazirine-functionalized mannosides for photoaffinity labeling: trouble with FimH

Femke Beiroth,
Tomas Koudelka,
Thorsten Overath,
Stefan D. Knight,
Andreas Tholey and
Thisbe K. Lindhorst

Full Research Paper
Published 24 Jul 2018

PDF
Album
1. Graphical Abstract
2. Figure 1: Principle of photoaffinity labeling of proteins with diazirine derivatives. Photolabile ligands are...
  
  Jump to Figure 1
3. Figure 2: FimH crystal structure (pdb code 1KLF) with docked p-nitrophenyl α-D-mannopyranoside (1, pNPMan). F...
  
  Jump to Figure 2
4. Figure 3: Based on the structure of the known FimH ligands 1 and 2, three photolabile α-D-mannosides, 3–5, we...
  
  Jump to Figure 3
5. Figure 4: Connolly representation of photolabile α-D-mannoside 3 in the closed gate (A, PDB code 1UWF) and op...
  
  Jump to Figure 4
6. Scheme 1: Synthesis of photolabile α-D-mannosides 3 and 4. a) H₂, Pd-C, methanol, rt, 6 h, 94%; b) HATU, DIPE...
  
  Jump to Scheme 1
7. Figure 5: ESIMS spectra of peptide M2 before (A) and after photoreaction (B) with mannoside 3.
  
  Jump to Figure 5
8. Figure 6: Intact protein ESIMS spectra of FimH_tr labeling with diazirine derivative 3 with (A) 50% acetonitri...
  
  Jump to Figure 6
Supp. Info

Beilstein J. Org. Chem. 2018, 14, 1890–1900, doi:10.3762/bjoc.14.163

Full Text

A hemicryptophane with a triple-stranded helical structure

Augustin Long,
Olivier Perraud,
Erwann Jeanneau,
Christophe Aronica,
Jean-Pierre Dutasta and
Alexandre Martinez

Full Research Paper
Published 24 Jul 2018

PDF
Album
1. Graphical Abstract
2. Scheme 1: Synthesis of 1.
  
  Jump to Scheme 1
3. Figure 1: ¹H NMR spectrum of 1 (400 MHz, CDCl₃).
  
  Jump to Figure 1
4. Figure 2: X-ray molecular structure of 1. Hydrogen atoms are omitted for clarity; dashed lines represent hydr...
  
  Jump to Figure 2
5. Figure 3: (a) Structure of compound 6. (b) ¹H NMR of 6 (CDCl₃, 400 MHz). (c) ¹H NMR of 1 (CDCl₃, 400 MHz).
  
  Jump to Figure 3
Supp. Info

Beilstein J. Org. Chem. 2018, 14, 1885–1889, doi:10.3762/bjoc.14.162

Full Text

Synthesis of 9-arylalkynyl- and 9-aryl-substituted benzo[b]quinolizinium derivatives by Palladium-mediated cross-coupling reactions

Siva Sankar Murthy Bandaru,
Darinka Dzubiel,
Heiko Ihmels,
Mohebodin Karbasiyoun,
Mohamed M. A. Mahmoud and
Carola Schulzke

Full Research Paper
Published 23 Jul 2018

PDF
Album
1. Graphical Abstract
2. Figure 1: Structures of 9-substituted benzo[b]quinolizinium derivatives 1 and 2.
  
  Jump to Figure 1
3. Scheme 1: Synthesis of benzo[b]quinolizinium-9-trifluoroborate (3b) and 9-arylbenzo[b]quinolizinium derivativ...
  
  Jump to Scheme 1
4. Scheme 2: Synthesis of 9-(arylethynyl)benzo[b]quinolizinium derivatives 2a–d.
  
  Jump to Scheme 2
5. Figure 2: Molecular structures of derivatives 2a (top) and 2b (bottom) in the solid state. Ellipsoids are sho...
  
  Jump to Figure 2
6. Figure 3: Absorption spectra of derivatives 2a (A), 2b (B), 2c (C) and, 2d (D); c = 20 μM; solvents: H₂O (mag...
  
  Jump to Figure 3
7. Figure 4: Emission spectra of derivatives 2a (A), 2c (B) and 2d (C); c = 20 μM; λ_ex = 375 nm; solvents: H₂O (...
  
  Jump to Figure 4
8. Figure 5: Photometric (A) and fluorimetric (B) acid-base titration of 2c; c = 20 μM in Britton–Robinson buffe...
  
  Jump to Figure 5
9. Figure 6: Photometric titration of 2a (A), 2b (B), 2c (C), and 2d (D) with ct DNA in BPE buffer (16 mM Na⁺; 5...
  
  Jump to Figure 6
10. Figure 7: Photometric titration of 2a (A), 2b (B), 2c (C) and 2d (D) with 22AG in potassium phosphate buffer ...
  
  Jump to Figure 7
11. Figure 8: Fluorimetric titration of 2a (A), 2b (B) and 2d (C) with ct DNA in potassium phosphate buffer (95 m...
  
  Jump to Figure 8
12. Figure 9: Fluorimetric titration of 2a (A) and 2d (B) with 22AG in potassium phosphate buffer (95 mM K⁺; 5% D...
  
  Jump to Figure 9
13. Scheme 3: Photoinduced charge transfer upon the excitation of derivative 2d.
  
  Jump to Scheme 3
Supp. Info