Tandem catalysis of ring-closing metathesis/atom transfer radical reactions with homobimetallic ruthenium–arene complexes
Beilstein J. Org. Chem. 2010, 6, 1167–1173. doi:10.3762/bjoc.6.133
Supporting Information
Full experimental procedures and spectral data for the new compounds, detailed crystallographic analysis of [(p-cymene)Ru(μ-Cl)3RuCl2(PCy3)] (7), and a cif file with crystallographic data for complex 7.
| Supporting Information File 1: Experimental procedures and spectral data. | ||
| Format: PDF | Size: 92.4 KB | Download |
| Supporting Information File 2: Detailed crystallographic analysis of complex 7. | ||
| Format: PDF | Size: 442.6 KB | Download |
| Supporting Information File 3: X-ray crystal data for complex 7. | ||
| Format: CIF | Size: 63.1 KB | Download |
References
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- Review
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Figure 1: Molecular structure of neutral platinum(II) complex 1 bearing four monodentate ligands; cy = cycloh...
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Figure 2: Chemical structure of the dinuclear Pt complexes 2a–b and 3 [20].
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Figure 3: Molecular structure of platinum(II) complexes bearing isoquinolinylpyrazolates; dip = 2,6-diisoprop...
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Figure 4: Selected neutral platinum(II) complexes featuring dianionic biazolate and neutral bipyridines [27].
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Figure 5: Selected neutral platinum(II) complexes from bipyrazolate and carbene-based chelates [34,35].
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Figure 6: Cyclometalated thiazol-2-ylidene platinum(II) complexes with different acetylacetonate ligands [37].
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Figure 7: Neutral platinum(II) complexes 13–15 bearing azolate ligands [13].
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Figure 8: Chemical structure of neutral platinum(II) complexes 16–18 bearing azine-pyrazolato bidentate ligan...
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Figure 9: Molecular structure of carbene-containing cyclometallated alkynylplatinum(II) complexes 19–21 [41].
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Figure 10: Chemical structure of platinum(II) complexes 22a–d bearing asymmetric C^N^N tridentate ligands [53].
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Figure 11: Chemical structure of platinum(II) complexes 23 bearing bis-cyclometalating 2,6-dipyridylbenzene ty...
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Figure 12: Molecular structure of dendritic carbazole-containing alkynyl-platinum(II) complexes 24a–d [62].
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Figure 13: Molecular structure of bipolar alkynyl-platinum(II) complexes 25 bearing carbazole and electron-acc...
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Figure 14: Molecular structures of neutral platinum(II) complexes comprising donor-acceptor alkynyls (26) or e...
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Figure 15: Chemical structure of the asymmetric Pt(II) derivatives 28 bearing triazole and tetrazole moieties ...
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Figure 16: Molecular structure of the tetradentate platinum complexes 29–32 bearing N^C^C^N and C^C^C^N ligand...
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Figure 17: Chemical structure of the tetradentate Pt complexes 33–38 based on N^C^C^N-type of ligands [80-84].
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Figure 18: Chemical structure of the macrocyclic tetradentate platinum complexes reported by Wang and co-worke...
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Figure 19: Molecular structure of complex 41–46 [88,89].
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Figure 20: Molecular structure of asymmetric derivatives 47–49 based on triaryl-type of bridge [90].
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Figure 21: Chemical structure of the asymmetric tetradentate derivatives 50 and 51 based on spirofluorene link...
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Figure 22: Molecular structure of the pyridylazolate-based complexes 52–54 reported by Chi and co-workers [97].
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Figure 23: Chemical structure of the red-to-NIR emitting complexes 55–57 bearing donor–acceptor triphenylamino...
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Figure 24: Molecular structures of the Pt(IV) derivatives 58 and 59 employed as triplet emitters in solution-p...
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Figure 1: Representative pharmaceutical agents bearing the CF3 group.
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Figure 2: The structures of the Togni reagents 1-(trifluoromethyl)-1,2-benziodoxol-3(1H)-one (1) and trifluor...
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Scheme 1: Our previous hypervalent iodine-mediated synthesis of 2H-azirine compounds.
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Scheme 2: Study on the presumed Togni reagent 1-mediated trifluoromethylation followed by PhIO-mediated aziri...
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Scheme 3: Togni reagent/PhIO-mediated one-pot synthesis of β-trifluoromethyl 2H-azirines. Reaction conditions...
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Scheme 4: Control study with TEMPO.
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Scheme 5: Proposed mechanism for the Togni reagent-mediated trifluoromethylation of enamines.
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Figure 1: Structures of compounds 1–8.
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Figure 2: Key COSY (bold line) and HMBC (arrow) correlations for 3.
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Figure 3: Referential 13C chemical shifts of an allylic carbon in burkholone [14] and haplacutine F [15].
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Scheme 1: Conventional water electrolyzer (a) and electrolyzer using an alternative anode reaction (b) in alk...
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Figure 1: XRD patterns of Co2Si, CoTe, CoAs. Cobalt is indicated by (+) and signals corresponding to the desi...
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Figure 2: Linear sweep voltammograms of CoP, CoB, CoTe, Co2Si, CoAs modified and blank Ni RDEs for the OER (a...
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Figure 3: SEM micrographs of bare (a, b) and CoB-modified (c, d) NF with 1000× or 20000× magnification, respe...
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Figure 4: a) Reaction pathways of HMF oxidation; b) chromatograms at various times during constant potential ...
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Figure 5: Concentration vs time curve for HMF, HMFCA, DFF, FFCA and FDCA (a); bar diagram of the faradaic eff...
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Figure 1: CVs of the electrooxidation of 1 M glycerol over Pd/NCNT and Pd/OCNT in 1 M KOH at 1000 rpm at a sc...
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Figure 2: CVs of the electrooxidation of 1 M glycerol over Pd/NCNT-NH3 and Pd/OCNT-He in 1 M NaOH at 1000 rpm...
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Figure 3: Comparison of IR spectra recorded at 0.77 and 1.17 V vs RHE (further potentials are shown in Supporting Information File 1, Figu...
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Scheme 1: Synthesis of dezocine by resolution.
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Scheme 2: Synthesis of catalysts C1–C17.
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Scheme 3: The proposed catalytic mechanism of stereoselective alkylation.
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Scheme 1: Nucleophilic and π-electrophilic characters of organometallics depending on the central metals.
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Scheme 2: Ni/Cr or Co/Cr-catalyzed NHK reaction.
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Scheme 3: Functionalization of alkynes via carbocobaltation.
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Scheme 4: Cyclization/borylation of alkynyl iodoarenes using the Co/Cr catalyst.
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Scheme 5: Three-component coupling of aryl iodides, arenes, and aldehydes using Co/Cr catalyst (this work).
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Scheme 6: Screening of aldehydes in the Co/Cr-catalyzed three-component coupling reaction. All yields are det...
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Scheme 7: Screening of aryl iodides in the Co/Cr-catalyzed three-component coupling reaction. All yields are ...
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Scheme 8: Screening of allenes in the Co/Cr-catalyzed three-component coupling reaction. All yields are deter...
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Scheme 9: Reversed diastereoselectivity using allenyl ethers 5 and 6. a4-chlorobenzaldehyde was used instead ...
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Scheme 10: Stoichiometric reaction of phenylchromium(II or III) reagents (reaction 1) and the three-component ...
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Scheme 11: The origin of the diastereoselectivity in the present three-component coupling.
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Scheme 12: Plausible reaction mechanism of the three-component coupling.
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Figure 1: Inherently chiral calix[4]arene-based phase-transfer catalysts.
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Scheme 1: Asymmetric alkylations of 3 catalyzed by (±)-1 and (±)-2 under phase-transfer conditions.
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Scheme 2: Synthesis of chiral calix[4]arene-based phase-transfer catalyst 7 and structure of O’Donnell’s N-be...
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Scheme 3: Asymmetric alkylation of glycine derivative 3 catalyzed by calixarene-based phase-transfer catalyst ...
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Figure 2: Calix[4]arene-amides used as phase-transfer catalysts.
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Scheme 4: Phase-transfer alkylation of 3 catalyzed by calixarene-triamide 12.
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Scheme 5: Synthesis of inherently chiral calix[4]arenes 20a/20b substituted at the lower rim. Reaction condit...
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Scheme 6: Asymmetric Henry reaction between 21 and 22 catalyzed by 20a/20b.
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Figure 3: Proposed transition state model of asymmetric Henry reaction.
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Scheme 7: Synthesis of enantiomerically pure phosphinoferrocenyl-substituted calixarene ligands 27–29.
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Scheme 8: Asymmetric coupling reaction of aryl boronates and aryl halides in the presence of calixarene mono ...
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Scheme 9: Asymmetric allylic alkylation in the presence of calix[4]arene ligand (S,S)-29.
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Figure 4: Structure of inherently chiral oxazoline calix[4]arenes applied in the palladium-catalyzed Tsuji–Tr...
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Scheme 10: Asymmetric Tsuji–Trost reaction in the presence of calix[4]arene ligands 36–39.
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Figure 5: BINOL-derived calix[4]arene-diphosphite ligands.
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Scheme 11: Asymmetric hydrogenation of 41a and 41b catalyzed by in situ-generated catalysts comprised of [Rh(C...
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Figure 6: Inherently chiral calix[4]arene 43 containing a diarylmethanol structure.
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Scheme 12: Asymmetric Michael addition reaction of 44 with 45 catalyzed by 43.
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Figure 7: Calix[4]arene-based chiral primary amine–thiourea catalysts.
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Scheme 13: Asymmetric Michael addition of 48 with 49 catalyzed by 47a and 47b.
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Scheme 14: Enantioselective Michael addition of 51 to 52 catalyzed by calix[4]arene thioureas.
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Scheme 15: Synthesis of calix[4]arene-based tertiary amine–thioureas 54–56.
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Scheme 16: Asymmetric Michael addition of 34 and 57 to nitroalkenes 49 catalyzed by 54b.
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Scheme 17: Synthesis of p-tert-butylcalix[4]arene bis-squaramide derivative 64.
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Scheme 18: Asymmetric Michael addition catalyzed by 64.
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Scheme 19: Synthesis of chiral p-tert-butylphenol analogue 68.
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Figure 8: Novel prolinamide organocatalysts based on the calix[4]arene scaffold.
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Scheme 20: Asymmetric aldol reactions of 72 with 70 and 71 catalyzed by 69b.
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Scheme 21: Synthesis of p-tert-butylcalix[4]arene-based chiral organocatalysts 75 and 78 derived from L-prolin...
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Scheme 22: Synthesis of upper rim-functionalized calix[4]arene-based L-proline derivative 83.
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Scheme 23: Synthesis and proposed structure of Calix-Pro-MN (86).
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Figure 9: Calix[4]arene-based L-proline catalysts containing ester, amide and acid units.
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Scheme 24: Synthesis of calix[4]arene-based prolinamide 92.
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Scheme 25: Calixarene-based catalysts for the aldol reaction of 21 with 70.
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Scheme 26: Asymmetric aldol reactions of 72 with cyclic ketones catalyzed by calix[4]arene-based chiral organo...
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Figure 10: A proposed structure for catalyst 92 in H2O.
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Scheme 27: Synthetic route for organocatalyst 98.
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Scheme 28: Asymmetric aldol reactions catalyzed by 99.
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Figure 11: Proposed catalytic environment for catalyst 99 in the presence of water.
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Scheme 29: Asymmetric aldol reactions between 94 and 72 catalyzed by 55a.
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Scheme 30: Enantioselective Biginelli reactions catalyzed by 69f.
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Scheme 31: Synthesis of calix[4]arene–(salen) complexes.
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Scheme 32: Enantioselective epoxidation of 108 catalyzed by 107a/107b.
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Scheme 33: Synthesis of inherently chiral calix[4]arene catalysts 111 and 112.
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Scheme 34: Enantioselective MPV reduction.
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Scheme 35: Synthesis of chiral calix[4]arene ligands 116a–c.
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Scheme 36: Asymmetric MPV reduction with chiral calix[4]arene ligands.
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Scheme 37: Chiral AlIII–calixarene complexes bearing distally positioned chiral substituents.
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Scheme 38: Asymmetric MPV reduction in the presence of chiral calix[4]arene diphosphites.
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Scheme 39: Synthesis of enantiomerically pure inherently chiral calix[4]arene phosphonic acid.
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Scheme 40: Asymmetric aza-Diels–Alder reactions catalyzed by (cR,pR)-121.
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Scheme 41: Asymmetric ring opening of epoxides catalyzed by (cR,pR)-121.
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Figure 1: Circular dichroism spectra of the novel peptides solved in 10 mM phosphate buffer (pH 7) (A), or ph...
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Figure 2: Cytotoxicity profiles of the peptides in MCF-7 and HeLa cells. Cells were incubated for 24 h with d...
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Figure 3: Cellular uptake in HeLa and MCF-7 cells. Cells were incubated for 30 min with 10 µM of CF-labeled p...
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Figure 4: Cellular uptake in MCF-7 and HeLa cells was quantified by flow cytometry. Cells were incubated with...
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Figure 5: Distribution pattern of the peptides in HeLa and MCF-7 cells when incubating 10 µM CF-labeled pepti...
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Figure 6: Cellular uptake in HeLa and MCF-7 cells when incubating the cells at 4 °C for 30 min with the CF-la...
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Figure 7: Uptake and delivery of DOX into HeLa and MCF-7 cells. Fluorescence microscopic images after 30 min ...
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Figure 1: Cryptands with 1,3,5-triphenylbenzene (1) and 2,4,6-triphenyl-1,3,5-triazine (2) aromatic reference...
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Scheme 1: Synthesis of cryptand 2.
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Figure 2: NMR spectra of cryptand 2: top, 1H NMR; bottom, 13C NMR.
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Figure 3: Chemical shift changes of the reference signal (belonging to the more deshielded protons of the p-p...
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Figure 4: The equilibrium geometry structure of cryptand 2 having 2,4,6-triphenyl-1,3,5-triazine caps.
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Figure 5: The equilibrium geometry structures of the cryptand–anthracene (a) and cryptand–pyrene (b) host–gue...
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Figure 6: The equilibrium geometry structure of the cryptand 2–1,5-dihydroxynaphthalene host–guest complex.
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Figure 7: The inclusion dynamics of the anthracene in the cavity of the cryptand for different constrained di...
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Scheme 1: Mannich reaction of N-Boc-isatin imines with ethyl nitroacetate (2) catalyzed by a cinchona alkaloi...
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Scheme 2: Mannich reaction of N-Boc-isatin imines with 1,3-dicarbonyl compounds catalyzed by a cinchona alkal...
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Scheme 3: Mannich reaction of N-alkoxycarbonylisatin imines with acetylacetone catalyzed by a cinchona alkalo...
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Scheme 4: Mannich reaction of isatin-derived benzhydrylketimines with trimethylsiloxyfuran catalyzed by a pho...
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Scheme 5: Mannich reaction of N-Boc-isatin imines with acetaldehyde catalyzed by a primary amine.
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Scheme 6: Mannich reaction of N-Cbz-isatin imines with aldehydes catalyzed by L-diphenylprolinol trimethylsil...
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Scheme 7: Addition of dimedone-derived enaminones to N-Boc-isatin imines catalyzed by a phosphoric acid.
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Scheme 8: Addition of hydroxyfuran-2-one-derived enaminones to N-Boc-isatin imines catalyzed by a phosphoric ...
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Scheme 9: Zinc-catalyzed Mannich reaction of N-Boc-isatin imines with silyl ketene imines.
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Scheme 10: Tin-catalyzed Mannich reaction of N-arylisatin imines with an alkenyl trichloroacetate.
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Scheme 11: Aza-Morita–Baylis–Hillman reaction of N-Boc-isatin imines with acrolein catalyzed by β-isocupreidin...
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Scheme 12: Aza-Morita–Baylis–Hillman reaction of N-Boc-isatin imines with acrolein (35) catalyzed by α-isocupr...
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Scheme 13: Aza-Morita–Baylis–Hillman reaction of N-Boc-isatin imines with maleimides catalyzed by β-isocupreid...
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Scheme 14: Aza-Morita–Baylis–Hillman reaction of N-Boc-isatin imines with nitroolefins catalyzed by a cinchona...
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Scheme 15: Friedel–Crafts reactions of N-Boc-isatin imines with 1 and 2-naphthols catalyzed by a cinchona alka...
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Scheme 16: Friedel–Crafts reactions of N-alkoxycarbonyl-isatin imines with 1 and 2-naphthols catalyzed by a ci...
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Scheme 17: Friedel–Crafts reaction of N-Boc-isatin imines with 6-hydroxyquinolines catalyzed by a cinchona alk...
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Scheme 18: Aza-Henry reaction of N-Boc-isatin imines with nitromethane catalyzed by a bifunctional guanidine.
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Scheme 19: Domino addition/cyclization reaction of N-Boc-isatin imines with 1,4-dithiane-2,5-diol (53) catalyz...
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Scheme 20: Nickel-catalyzed additions of methanol and cumene hydroperoxide to N-Boc-isatin imines.
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Scheme 21: Palladium-catalyzed addition of arylboronic acids to N-tert-butylsulfonylisatin imines.
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Scheme 1: Thermal reaction of sydnones with symmetrical alkynes.
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Scheme 2: Reaction of sydnones with strained cycloalkynes.
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Scheme 3: Reaction of sydnones with didehydrobenzenes.
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Scheme 4: Formation of isomeric pyrazole dicarboxylates.
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Scheme 5: Mechanism of thermal cycloaddition between sydnones and alkynes.
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Scheme 6: Mechanism of photochemical reaction of sydnones with symmetrical alkynes.
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Scheme 7: HOMO–LUMO diagram for thermal [3 + 2]-cycloaddition of sydnones with alkynes.
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Scheme 8: Synthetic strategy leading to 1,2-disubstituted pyrazoles.
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Scheme 9: Unsuccessful reaction with phenylpropiolic acid.
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Scheme 10: Synthetic strategy leading to 1,4,5-trisubstituted pyrazoles.
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Scheme 11: Reaction of sydnones carrying in position 4- six-membered 2-N-heterocyclic ring.
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Scheme 12: Strain-promoted sydnone alkyne cycloaddition (SPSAC).
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Scheme 13: Synthesis of a key intermediate of niraparib.
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Scheme 14: Reaction of sydnones with 1,3-/1,4-benzdiyne equivalents.
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Scheme 15: Reaction of sydnones with heterocyclic strained cycloalkynes.
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Scheme 16: Mono-copper catalyzed cycloaddition reaction.
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Scheme 17: Di-copper catalyzed cycloaddition reaction.
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Scheme 1: Biosynthesis of AHLs by ACP-dependent LuxI type enzymes.
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Figure 1: Total ion chromatograms of the FAME extracts of A) P. inhibens 2.10, B) P. inhibens DSM17395, C) P....
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Scheme 2: Synthesis of N-pantothenoylcysteamine thioesters (PCEs) for feeding experiments with AHL synthases.
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Figure 2: Total ion chromatograms of the extracts from competition experiments using recombinant PgaI2 from P...
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Figure 1: Biological action of single-stranded oligonucleotides (ON): antigene and antisense pathways.
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Figure 2: Selected examples 1–6 of nucleic acid modifications based on additionally attached positively charg...
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Figure 3: Oligonucleotide analogues with artificial cationic backbone linkages discussed in this review: amin...
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Scheme 1: Structure of Letsinger's modified deoxyadenosyl dinucleotide 11 and synthesis of cationic oligonucl...
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Figure 4: Artificial cationic backbone linkages 19 and 20 which are structurally related to aminoalkylated ph...
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Scheme 2: Bruice's synthesis of guanidinium-linked DNG oligomer 29 in the 5'→3' direction (Troc = 2,2,2-trich...
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Scheme 3: Bruice's synthesis of purine-containing guanidinium-linked DNG oligomer 36 in the 3'→5' direction (...
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Scheme 4: Bruice's synthesis of S-methylthiourea-linked DNmt oligomer 43.
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Figure 5: Structure of the natural product muraymycin A1 (44) and design concept of nucleosyl amino acid (NAA...
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Scheme 5: Retrosynthetic summary of Ducho's synthesis of partially zwitterionic NAA-modified oligonucleotides ...
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Scheme 6: Retrosynthetic summary of Ducho's and Grossmann's synthesis of fully cationic NAA-modified oligonuc...
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Scheme 1: Envisaged approach for the synthesis of 5-chloropyrazole-4-carboxylates 2.
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Scheme 2: Synthesis of bipyrazolone 3a.
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Figure 1: Signal of the OCH2 ester protons of reaction product 3a (500 MHz, CDCl3).
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Figure 2: ORTEP-plot of the crystal structure of compound 3a drawn with 50% displacement ellipsoids [(4S,4'S)-...
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Figure 3: Arrangement (4R,4'R)- and (4S,4'S)-3a enantiomers in the crystal unit drawn with 50% displacement e...
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Scheme 3: Synthesis of compounds 3a–i.
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Scheme 4: Reaction of different 5-hydroxypyrazoles with thionyl chloride.
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Scheme 5: Reaction of 1a with sulfuryl chloride.
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Scheme 6: Possible reaction mechanism for the transformation 1 → 3.
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Scheme 7: Preparation of bipyrazoles 10.
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Figure 4: 1H NMR (italics), 13C NMR (normal letters) and 15N NMR (in bold) chemical shifts of 3a (in CDCl3).
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Figure 1: Cryptophycin-1 (1) and -52 (2).
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Scheme 1: Synthesis of modified unit B (13 and 14). Reagents and conditions: (a) 1) TsCl, DMAP, Et3N, CH2Cl2,...
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Scheme 2: Synthesis of cryptophycin analogues 22, 23 and 24. Reagents and conditions: (a) 4-DMAP, 2,4,6-trich...
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Figure 2: Binding mode of 2, showing the interaction to the vinca domain peptide binding pocket (blue). Hydro...
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Figure 3: Docking of 22 to the vinca domain of β-tubulin. Surface and backbone of β-tubulin are shown in blue...
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Figure 4: Docking of 24 to β-tubulin. Surface and backbone of β-tubulin are shown in blue, GDP in yellow. H-b...
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Scheme 1: Overview of different types of iodane-based group-transfer reactions and their atom economy based o...
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Scheme 2: (a) Structure of diaryliodonium salts 1. (b) Diarylation of a suitable substrate A with one equival...
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Scheme 3: Synthesis of biphenyls 3 and 3’ with symmetrical diaryliodonium salts 1.
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Scheme 4: Synthesis of diaryl thioethers 5.
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Scheme 5: Synthesis of two distinct S-aryl dithiocarbamates 7 and 7’ from one equivalent of diaryliodonium sa...
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Scheme 6: Synthesis of substituted isoindolin-1-ones 9 from 2-formylbenzonitrile 8 and the postulated reactio...
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Scheme 7: Domino C-/N-arylation of indoles 10.
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Scheme 8: Domino modification of N-heterocycles 12 via in situ-generated directing groups.
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Scheme 9: Synthesis of triarylamines 17 through a double arylation of anilines.
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Scheme 10: Selective conversion of novel aryl(imidazolyl)iodonium salts 1b to 1,5-disubstituted imidazoles 18.
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Scheme 11: Selected examples for the application of cyclic diaryliodonium salts 19.
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Scheme 12: Tandem oxidation–arylation sequence with (dicarboxyiodo)benzenes 20.
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Scheme 13: Oxidative α-arylation via the transfer of an intact 2-iodoaryl group.
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Scheme 14: Tandem ortho-iodination/O-arylation cascade with PIDA derivatives 20b.
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Scheme 15: Synthesis of meta-N,N-diarylaminophenols 28 and the postulated mechanism.
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Scheme 16: (Dicarboxyiodo)benzene-mediated metal-catalysed C–H amination and arylation.
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Scheme 17: Postulated mechanism for the amination–arylation sequence.
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Scheme 18: Auto-amination and cross-coupling of PIDA derivatives 20c.
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Scheme 19: Tandem C(sp3)–H olefination/C(sp2)–H arylation.
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Scheme 20: Atom efficient functionalisations with benziodoxolones 36.
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Scheme 21: Atom-efficient synthesis of furans 39 from benziodoxolones 36a and their further derivatisations.
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Scheme 22: Oxyalkynylation of diazo compounds 42.
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Scheme 23: Enantioselective oxyalkynylation of diazo compounds 42’.
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Scheme 24: Iron-catalysed oxyazidation of enamides 45.
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- Review
- Published 30 May 2018
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Scheme 1: An overview of different chiral iodine reagents or precursors thereof.
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Scheme 2: Asymmetric oxidation of sulfides by chiral hypervalent iodine reagents.
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Scheme 3: Oxidative dearomatization of naphthol derivatives by Kita et al.
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Scheme 4: [4 + 2] Diels–Alder dimerization reported by Birman et al.
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Scheme 5: m-CPBA guided catalytic oxidative naphthol dearomatization.
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Scheme 6: Oxidative dearomatization of phenolic derivatives by Ishihara et al.
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Scheme 7: Oxidative spirocyclization applying precatalyst 11 developed by Ciufolini et al.
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Scheme 8: Asymmetric hydroxylative dearomatization.
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Scheme 9: Enantioselective oxylactonization reported by Fujita et al.
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Scheme 10: Dioxytosylation of styrene (47) by Wirth et al.
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Scheme 11: Oxyarylation and aminoarylation of alkenes.
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Scheme 12: Asymmetric diamination of alkenes.
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Scheme 13: Stereoselective oxyamination of alkenes reported by Wirth et al.
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Scheme 14: Enantioselective and regioselective aminofluorination by Nevado et al.
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Scheme 15: Fluorinated difunctionalization reported by Jacobsen et al.
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Scheme 16: Aryl rearrangement reported by Wirth et al.
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Scheme 17: α-Arylation of β-ketoesters.
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Scheme 18: Asymmetric α-oxytosylation of carbonyls.
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Scheme 19: Asymmetric α-oxygenation and α-amination of carbonyls reported by Wirth et al.
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Scheme 20: Asymmetric α-functionalization of ketophenols using chiral quaternary ammonium (hypo)iodite salt re...
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Scheme 21: Oxidative Intramolecular coupling by Gong et al.
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Scheme 22: α-Sulfonyl and α-phosphoryl oxylation of ketones reported by Masson et al.
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Scheme 23: α-Fluorination of β-keto esters.
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Scheme 24: Alkynylation of β-ketoesters and amides catalyzed by phase-transfer catalyst.
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Scheme 25: Alkynylation of β-ketoesters and dearomative alkynylation of phenols.
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Scheme 1: Half-lives for the thermal Z→E isomerization of all-meta-alkyl-substituted azobenzenes 1–3 in DMSO ...
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Scheme 2: Isomerization of N-substituted Z-azobenzenes (a). Rotational equilibrium of (Z)-4 allowing intramol...
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Figure 1: a) Optimized geometry of open conformer (R,S)-4 c0. b) NCI plot of the most stable conformer of (R,S...
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Figure 1: Structures of biologically active diarylmethanes and commercially available pharmaceuticals based o...
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Scheme 1: Various synthetic approaches to diarylmethanols (literature review and this work).
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Scheme 2: A general strategy for the synthesis of ortho-1,3-dithianylaryl(aryl)methanols 5 and 6, and their r...
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Scheme 3: Attempts of the OH removal in ortho-1,3-dithianyl- 6b and ortho-1,3-dioxanylaryl(aryl)methanols 9 u...
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- Letter
- Published 28 May 2018
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Figure 1: Bioactive pyrazolo[1,5-a]pyrimidinones.
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Scheme 1: Synthesis of 5-aminopyrazoles. Reaction conditions: ketonitrile (2.0 mmol, 1.0 equiv), hydrazine (2...
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Scheme 2: One-pot synthesis of pyrazolo[1,5-a]pyrimidinones. aReaction conditions: ketonitrile (0.9 mmol, 1.0...
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Figure 2: X-ray crystal structure of pyrazolo[1,5-a]pyrimidinone 3m with ellipsoids at 50% probability.
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- Published 28 May 2018
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Scheme 1: Investigation of alkynylbenziodoxole derivatives for radical alkynylations.
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Scheme 2: Synthesis and characterization of BI-alkyne derivatives 3a–f.
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Scheme 3: Reaction of alkynylbenziodoxole derivatives for deboronative alkynylation in photoredox catalysis. ...
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Scheme 4: Reaction of alkynylbenziodoxole derivatives for radical alkynylations in photoredox catalysis. Reac...
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Scheme 5: Reaction of alkynylbenziodoxole derivatives for acyl radical alkynylation in photoredox catalysis. ...
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Scheme 6: Mechanistic investigations of alkynylbenziodoxole for radical acceptor and oxidative quenching reac...
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Scheme 7: The role of alkynylbenziodoxole derivatives for radical alkynylation in photoredox catalysis.
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- Published 25 May 2018
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Figure 1: Bioactive compounds with pyridinone, quinolone and indole cores.
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Scheme 1: C–H functionalization of pyridinones and quinoline N-oxides.
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Scheme 2: Scope and limitations of the Rh-catalyzed C–H activation of [1,2'-bipyridin]-2-one.
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Scheme 3: Scope of the Rh-catalyzed peri C–H activation of quinoline N-oxides.
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Scheme 4: Product modifications.
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Scheme 1: Mechanistic hypothesis.
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Scheme 2: Extension of the method.
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Scheme 3: Carbon-based nucleophiles.
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Scheme 4: THF ring opening.
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Scheme 1: Generation and reaction of cationic species generated by “indirect cation pool” methods.
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Figure 1: (a) 1H NMR of N-acyliminium ion C1 in CD2Cl2 at −80 °C (600 MHz). (b) Preferred conformation of C1.
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Figure 2: (a) 1H NMR spectrum of C3 in CD2Cl2 at −60 °C (400 MHz). (b) Preferred conformation of C3.
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Figure 3: (a) 1H NMR spectrum of C5 in CD2Cl2 at −60 °C (400 MHz). (b) Preferred conformation of C5.
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Figure 4: Summary of the conformations of N-acyliminium ions C1–C6.
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Figure 5: Stevens’ hypothesis on the tendency of the addition of nucleophiles to N-acyliminium ions. The subs...
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Figure 6: A plausible mechanism of the observed diastereoselective reaction of the N-acyliminium ions.
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Figure 7: Comparison of ΔG for the pseudo-equatorial and pseudo-axial conformations of C1–C6 at the B3LYP/6-3...
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