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. | ||
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Supporting Information File 2: Detailed crystallographic analysis of complex 7. | ||
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Supporting Information File 3: X-ray crystal data for complex 7. | ||
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Graphical Abstract
Figure 1: Representative pyrrolo[3,4-c]pyrrole-1,3-diones and polysubstituted pyrrole derivatives.
Scheme 1: Synthetic pathway for the preparation of pyrrolo[3,4-c]pyrrole-1,3-diones and highly substituted py...
Scheme 2: Scope of one-pot synthesis of pyrrolo[3,4-c]pyrrole-1,3-diones 12a–k. General reaction conditions: ...
Scheme 3: Scope of the synthesis of highly substituted pyrrole derivatives 13a–n. General reaction conditions...
Scheme 4: Synthesis of 13k from 12d and ethylamine.
Graphical Abstract
Scheme 1: Previously reported post-Ugi-4CR methods for the synthesis of 2-oxindoles and spirocyclic 2-oxindol...
Scheme 2: Post-Ugi-4CR/transamidation/cyclization sequence.
Scheme 3: Base-promoted intramolecular 5-endo-dig cyclization.
Figure 1: ORTEP diagram of compound 7a.
Figure 2: Readily and synthetically accessible starting materials.
Scheme 4: Reaction scope with varying combinations of substrates.
Scheme 5: Synthesis of 5-chloro-1'-phenylspiro[indoline-3,2'-pyrrolidine]-2,5'-dione (8a).
Figure 3: Small molecule library of spiro[indoline-3,2'-pyrrolidine]-2,5'-dione analogs.
Scheme 6: Method applicability for the one-pot synthesis of 5-HT6 receptor antagonist 8j [53].
Graphical Abstract
Scheme 1: Synthetic routes of CEPDO and CBPDO.
Figure 1: Structures and molecular orbitals of (a) CEPDO and (b) CBPDO.
Figure 2: UV–vis absorption and photoluminescence spectra in DCM solution (1 × 10−5 M and 1 × 10−6 M, respect...
Figure 3: Cyclic voltammograms for CEPDO and CBPDO in DCM solution.
Figure 4: DSC and TGA curves of CEPDO and CBPDO.
Graphical Abstract
Scheme 1: Anodic oxidation of amides.
Scheme 2: Anodic oxidation of an amide in the presence of alkene.
Scheme 3: Intramolecular cyclization via anodic oxidation of an eneamide.
Scheme 4: Anodic bond cleavages in amides of type Ph2CHCONHAr.
Scheme 5: Type of products obtained (n = 0, 1, 2).
Scheme 6: Synthesized cyclic N-acyl and N-sulfonyl piperidines for electrolysis.
Scheme 7: Type of bisamides (derived from diamines) studied (n = 2, 3, 4).
Scheme 8: Type of products obtained from anodic oxidation of II-3.
Scheme 9: Anodic splitting of C–C bond in bisamides in the presence of LiClO4 electrolyte.
Scheme 10: Anodic splitting of C–C bond in bisamides in the presence of Et4NBF4 electrolyte.
Scheme 11: A suggested mechanism for anodic methoxylation of amides.
Scheme 12: Mechanisms of formation of fragmentation products.
Graphical Abstract
Figure 1: Four possible isomers reachable through the presented approach.
Scheme 1: Sharpless epoxidation to gain D-galacto- 5a and L-galacto-configured epoxythreitol 5b.
Scheme 2: Reagents and conditions: a) i) (COCl)2, DMSO, Et3N, DCM, ii) triethyl phosphonoacetate, NaH, DCM; b...
Scheme 3: Proposed mechanism of the Pd-catalyzed azide substitution of 6a in protic solvent.
Scheme 4: Approach towards peracetylated D-IdoNAc 2c, reactions and conditions: a) Ti(OiPr)4, t-BuOOH, D-DET,...
Graphical Abstract
Graphical Abstract
Figure 1: Schematic representation of (a) the cholesterol molecule; (b) the β-cyclodextrin molecule.
Figure 2: (a) Crystal structure of the inclusion compound of cholesterol in β-CD dimer. Water molecules are o...
Figure 3: RMSD over time for all CHL (green) and β-CD (blue) atoms (a) at 300 K and (b) at 340 K.
Figure 4: Representative snapshots of the CHL/β-CD inclusion complex at 0 (a, c) and 11 ns (b, d) in timescal...
Figure 5: (a) Distance between the O1 atom (CHL) and the centroid DK of the O4n atoms of host A at 300 (green...
Graphical Abstract
Figure 1: Enzymatic cleavage of phosphodiester linkages of DNA and RNA.
Figure 2: Energy profiles for a concerted ANDN (A) and stepwise mechanisms (AN + DN) with rate-limiting break...
Figure 3: Pseudorotation of a trigonal bipyramidal phosphorane intermediate by Berry pseudorotation [20].
Figure 4: Protolytic equilibria of phosphorane intermediate of RNA transesterification.
Figure 5: Structures of acyclic analogs of ribonucleosides.
Figure 6: First-order rate constants for buffer-independent partial reactions of uridyl-3´,5´-uridine at pH 5...
Scheme 1: pH- and buffer-independent cleavage and isomerization of RNA phosphodiester linkages. Observed firs...
Scheme 2: Mechanism for the pH- and buffer-independent cleavage of RNA phosphodiester linkages.
Scheme 3: Hydroxide-ion-catalyzed cleavage of RNA phosphodiester linkages.
Scheme 4: Anslyn's and Breslow's mechanism for the buffer-catalyzed cleavage and isomerization of RNA phospho...
Scheme 5: General base-catalyzed cleavage of RNA phosphodiester bonds.
Scheme 6: Kirby´s mechanism for the buffer-catalyzed cleavage of RNA phosphodiester bonds [65].
Figure 7: Guanidinium-group-based cleaving agents of RNA.
Scheme 7: Tautomers of triazine-based cleaving agents and cleavage of RNA phosphodiester bonds by these agent...
Figure 8: Bifunctional guanidine/guanidinium group-based cleaving agents of RNA.
Scheme 8: Cleavage of HPNP by 1,3-distal calix[4]arene bearing two guanidine groups [80].
Figure 9: Cyclic amine-based cleaving agents of RNA.
Scheme 9: Mechanism for the pH-independent cleavage and isomerization of model compound 12a in the pH-range 7...
Scheme 10: Mechanism for the pH-independent cleavage of guanylyl-3´,3´-(2´-amino-2´-deoxyuridine) at pH 6-8 [89].
Scheme 11: Cleavage of uridine 3´-dimethyl phosphate by A) intermolecular attack of methoxide ion and B) intra...
Scheme 12: Transesterification of group I introns and hydrolysis of phosphotriester models proceed through a s...
Scheme 13: Cleavage of trinucleoside 3´,3´,5´-monophosphates by A) P–O3´ and B) P–O5´ bond fission.
Figure 10: Model compounds (23–25) and metal ion binding ligands used in kinetic studies of metal-ion-promoted...
Figure 11: Zn2+-ion-based mono- and di-nuclear cleaving agents of nucleic acids.
Figure 12: Miscellaneous complexes and ligands used in kinetic studies of metal-ion-promoted cleavage of nucle...
Figure 13: Azacrown ligands 34 and 35 and dinuclear Zn2+ complex 36 used in kinetic studies of metal-ion-promo...
Figure 14: Metal ion complexes used for determination of βlg values of metal-ion-promoted cleavage of RNA mode...
Figure 15: Metal ion complexes used in kinetic studies of medium effects on the cleavage of RNA model compound...
Scheme 14: Alternative mechanisms for metal-ion-promoted cleavage of phosphodiesters.
Figure 16: Nucleic acid cleaving agents where the attacking oxyanion is not coordinated to metal ion.
Graphical Abstract
Scheme 1: Reactions of substituted allenes with HVI reagents.
Scheme 2: Chlorination of p-tolylallene (2a) with (dichloroiodo)benzene (1a).
Scheme 3: Chlorination of various aryl-substituted allenes. General conditions: Allene 2a (0.2 mmol, 1 equiv)...
Scheme 4: Chlorination of various α-substituted phenylallene derivatives. General conditions: Allene 2a (0.2 ...
Scheme 5: Chlorination of methoxy-substituted α-methyl phenylallenes. General conditions: Allene 2a (0.2 mmol...
Scheme 6: Control reactions: (a) chlorination of deuterated biphenylallene [D2]-2b; (b) reaction with TEMPO.
Figure 1: Proposed reaction mechanism.
Graphical Abstract
Scheme 1: Representative pharmaceutically useful indazoles.
Scheme 2: Model Heck reaction of 3-bromo-N-methyl-1H-indazole (1a) and n-butyl acrylate (2a). (173 stainless-...
Figure 1: Investigation of additives in the Heck reaction: 1a (1.5 mmol), 2a (2.25 mmol), Pd(OAc)2 (5 mol %),...
Scheme 3: The control experiments. aTEA (1.8 mmol), silica gel (5.0 g), bPd(OAc)2 (5 mol %), PPh3 (10 mol %),...
Scheme 4: Plausible reaction pathway.
Figure 2: Influence of milling time and rotation speed on the Heck reaction: 1a (1.5 mmol), 2a (2.25 mmol), P...
Figure 3: Influence of the milling ball filling degree with different size on the Heck reaction: 1a (1.5 mmol...
Scheme 5: Examination of the substrate scope. Reaction conditions: 1 (1.5 mmol), 2 (2.25 mmol), Pd(OAc)2 (5 m...
Scheme 6: Synthesis of axitinib by mechanochemical Heck–Migita coupling. Reagents and conditions: (i) NBS, Na...
Graphical Abstract
Figure 1: Structural components of nucleic acids. Shown is the monomeric building block of nucleic acids. Cha...
Figure 2: Formation of oxocarbenium ion during glycosidic bond cleavage in nucleosides [31]. The extent of leavin...
Figure 3: Structural modifications to nucleobase-sugar connectivity. The O–C–N bond between nucleobase and su...
Figure 4: Examples of natural and synthetic C-nucleosides. Pseudouridine and formcycin are among several natu...
Figure 5: Synthetic approaches to C-nucleosides. A. Two common strategies for C-nucleoside synthesis involve ...
Figure 6: Steroselective C-nucleoside synthesis using D-ribonolactone. A. Nucleophilic substitution of D-ribo...
Figure 7: Synthesis of C1'-substituted 4-aza-7,9-dideazaadenine C-nucleosides [63-65,69,70]. A. Reaction of D-ribonolacton...
Figure 8: Pyrrolo- and imidazo[2,1-f][1,2,4]triazine C-nucleosides. A series of sugar- and nucleobase-substit...
Figure 9: Synthesis of 1',2'-cyclopentyl C-nucleoside [73]. Functional groups at C1' and C2' were installed and e...
Figure 10: Anti-influenza C-nucleosides mimicking favipiravir riboside [74]. A. Structure of favipiravir and its r...
Figure 11: Alternative method for synthesis of 2'-substituted C-nucleosides [75]. A. Synthesis of C2'-substituted ...
Figure 12: Synthesis of carbocyclic C-nucleosides using cyclopentanone [53]. A. Nucleophlic substitution on cyclop...
Figure 13: Synthesis of carbocyclic C-nucleosides via Suzuki coupling [53]. A. Synthesis of OTf-cyclopentene that ...
Graphical Abstract
Scheme 1: Syntheses of GnRH-III–[(4Lys(Bu)/4Ser, 6Aaa, 8Lys(Dau=Aoa)] bioconjugates. a) (1) 2% hydrazine in D...
Figure 1: Far-UV ECD spectra of GnRH-III and its drug conjugates in water (GnRH-III solid, K1 dash, K2 dot, 1...
Figure 2: Degradation of the GnRH-III bioconjugates by rat liver lysosomal homogenate. A) Cleavage sites prod...
Figure 3: Cytostatic effect of the GnRH-III bioconjugates at different concentrations on A) HT-29 and B) MCF-...
Figure 4: Cellular uptake of the GnRH-III bioconjugates at different concentrations on A) HT-29 and B) MCF-7 ...
Figure 5: Cellular uptake of bioconjugate K2 (40 µM) visualized by confocal laser scanning microscopy (CLSM) ...
Figure 6: Competitive inhibition of the GnRH-R on MCF-7 cells. Cellular uptake of the GnRH-III bioconjugate K2...
Graphical Abstract
Figure 1: Structures of the studied hydroxyflavone derivatives.
Figure 2: Optimized geometries for (a) DEHF∙ATP, (b) UHF∙ATP with the adenine of ATP “sandwiched” between the...
Scheme 1: Synthesis of UHF. (i) 4-Dimethylaminobenzaldehyde, DMF, NaOMe, rt, 17 h, (ii) hydrogen peroxide, Na...
Figure 3: Variation of fluorescence spectra of UHF (1.0 μM) upon addition of increasing amounts of ATP in 0.0...
Figure 4: Excitation spectra of UHF (dark green line, 1 μM) and UHF + 300 equiv ATP (red line), measured at d...
Figure 5: Fluorescence enhancement (F/F0) values of UHF (1.0 μM) upon addition of different nucleotides at 54...
Figure 6: Ratio of the fluorescence intensities at 540 nm, the samples were excited at 470 and 400 nm. The re...
Graphical Abstract
Figure 1: Structures of the widespread fungal volatiles oct-1-en-3-ol (1) and 6-pentyl-2H-pyran-2-one (2), th...
Figure 2: Total-ion chromatogram of the bouquet from Hypoxylon invadens MUCL 54175 obtained by the CLSA heads...
Figure 3: Identified volatile organic compounds from Hypoxylon invadens MUCL 54175.
Figure 4: Mass spectra of volatiles from Hypoxylon invadens MUCL 54175. Mass spectra of A) 2,5-dimethylphenol...
Scheme 1: Proposed common biosynthetic pathway to volatile aromatic compounds from Hypoxylon invadens.
Scheme 2: Synthesis of 5-hydroxy-2-methyl-4H-chromen-4-one (19).
Graphical Abstract
Figure 1: Assembly of catalyst-functionalized amphiphilic block copolymers into polymer micelles and vesicles...
Scheme 1: C–N bond formation under micellar catalyst conditions, no organic solvent involved. Adapted from re...
Scheme 2: Suzuki−Miyaura couplings with, or without, ppm Pd. Conditions: ArI 0.5 mmol 3a, Ar’B(OH)2 (0.75–1.0...
Figure 2: PQS (4a), PQS attached proline catalyst 4b. Adapted from reference [26]. Copyright 2012 American Chemic...
Figure 3: 3a) Schematic representation of a Pickering emulsion with the enzyme in the water phase (i), or wit...
Scheme 3: Cascade reaction with GOx and Myo. Adapted from reference [82].
Figure 4: Cross-linked polymersomes with Cu(OTf)2 catalyst. Reprinted with permission from [15].
Figure 5: Schematic representation of enzymatic polymerization in polymersomes. (A) CALB in the aqueous compa...
Figure 6: Representation of DSN-G0. Reprinted with permission from [100].
Figure 7: The multivalent esterase dendrimer 5 catalyzes the hydrolysis of 8-acyloxypyrene 1,3,6-trisulfonate...
Figure 8: Conversion of 4-NP in five successive cycles of reduction, catalyzed by Au@citrate, Au@PEG and Au@P...
Graphical Abstract
Scheme 1: Cobalt–NHC-catalyzed C–H alkenylation reactions with alkenyl electrophiles.
Scheme 2: Reaction of substituted pivalophenone N–H imines with 2a. aThe major regioisomer is shown (rr = reg...
Scheme 3: Reaction of 1a with various alkenyl phosphates. aA mixture of E- and Z-alkenyl phosphate (ca. 1:1) ...
Scheme 4: The cyclization of o-alkenylpivalophenone N–H imine.
Scheme 5: Proposed catalytic cycle (R = t-BuCH2, R' = P(O)(OEt)2).
Graphical Abstract
Scheme 1: Radical cation Diels–Alder reaction of trans-anethole [17].
Scheme 2: Radical cation Diels–Alder reactions of aryl vinyl ether and sulfides [17,25].
Scheme 3: Radical cation Diels–Alder reaction of aryl vinyl ether (1). Conditions: 1.0 M LiClO4/CH3NO2, carbo...
Scheme 4: Oxidative SET-triggered reaction of aryl vinyl ether 1c. Conditions: 1.0 M LiClO4/CH3NO2, carbon fe...
Figure 1: GC–MS Monitoring of the oxidative SET-triggered reaction of aryl vinyl ether 1c.
Scheme 5: Oxidative SET-triggered rearrangement of vinyl cyclobutane 4. Conditions: 1.0 M LiClO4/CH3NO2, carb...
Scheme 6: Unsuccessful rearrangement of cyclobutanes. Conditions: 1.0 M LiClO4/CH3NO2, carbon felt electrodes...
Scheme 7: Proposed mechanism for the radical cation Diels–Alder reaction of aryl vinyl ether 1.
Graphical Abstract
Scheme 1: Enzymatic reaction schemes for the selective oxidation of trans-hex-2-enol. A: Alcohol dehydrogenas...
Figure 1: Michaelis–Menten kinetics of the PeAAOx-catalysed oxidation of trans-hex-2-enol. Conditions: 50 mM ...
Figure 2: The influence of the residence time on the conversion of trans-hex-2-enol (red squares) to trans-2-...
Figure 3: Increasing the PeAAOx turnover numbers (TN) by increasing the residence time. Conditions: 6 mL flow...
Graphical Abstract
Figure 1: Solution-based Wittig reaction mechanism.
Figure 2: 1H NMR spectra of stilbene mixture (a) and benzyl benzoate (b).
Scheme 1: Possible mechanism of benzyl benzoate formation.
Scheme 2: A possible mechanistic explanation for the E selectivity.
Scheme 3: Ball-milled Wittig reaction using excess benzaldehyde.
Figure 3: Comparison of solution based Wittig reaction (a) with polymer-supported mechanochemical Wittig reac...
Scheme 4: Stepwise ball-milled Wittig reaction with ethanol as the LAG solvent.
Scheme 5: Stepwise ball-milled Wittig reaction with ethanol evaporation between the steps.
Graphical Abstract
Scheme 1: Azidation of per O-acetylated glucose.
Graphical Abstract
Scheme 1: Molecular structures of isomers 1 and 2.
Figure 1: (a) The optimized S0 geometries of 1 (left) and 2 (right) on B3LYP/6-31G* level in gas phase; (b) T...
Figure 2: UV–vis (solid point) and photoluminescence (hollow point) spectra of 1 and 2 in dilute solution.
Figure 3: The low temperature photoluminescence spectra of 1 (left) and 2 (right) in toluene at 77 K.
Figure 4: (a) Time-resolved transient photoluminescence decay spectra of the doped films (8 wt % in CBP) meas...
Figure 5: Energy level (eV) diagrams of OLED devices and the chemical structures of the materials utilized fo...
Figure 6: J–V–L (current density–voltage–luminance) (left) and EQE–current density characteristics of the dev...
Figure 7: EQE–current density characteristics of the devices based on 1 (top) and 2 (bottom). The solid lines...
Graphical Abstract
Scheme 1: Synthesis of complexes 2 and 3.
Figure 1: ORTEP representation of 3. Thermal ellipsoids are drawn at the 50% probability level. Selected bond...
Figure 2: UV–vis absorption spectra of complexes 2 and 3 measured in dichloromethane at room temperature.
Figure 3: Emission spectra of complexes 2 and 3 measured at room temperature and 77 K, 2 wt % in a PMMA matri...
Figure 4: Cyclic voltammograms of complexes 2 and 3, analyte concentration 10−4 M. Measured in DMF (0.1 M TBA...
Figure 5: Thin films of Pt(MPIM)(acac) left, Pt(MPIM)(mes) (2) middle, and Pt(MPIM)(dur) (3) right, 2 wt % in...
Figure 6: Photoluminescence spectra of 2 and 3 compared to the emission profile of Pt(MPIM)(acac), 2 wt % in ...
Figure 7: Localization of spin density on the complexes Pt(MPIM)(acac) left, Pt(MPIM)(mes) (2) middle, and Pt...
Graphical Abstract
Scheme 1: Enantioselective dioxytosylation of styrene as a seminal example.
Figure 1: Series of lactate-based hypervalent iodine reagents.
Scheme 2: Plausible pathways in dioxytosylation of styrenes.
Graphical Abstract
Figure 1: Targeted integrated multistep synthesis of valsartan (1) and sacubitril (2).
Scheme 1: Suzuki–Miyaura coupling of phenylboronic acid 3 with various bromoarenes 4a–e (a: R1 = H, R2 = CH3; ...
Figure 2: Particle size distribution of Ce0.495Sn0.495Pd0.01O2–δ after size reduction via milling and separat...
Figure 3: Optical microscope images of fresh aqueous dispersions, 0.05 wt %, of (a) Ce0.495Sn0.495Pd0.01O2–δ ...
Figure 4: Photos of vessels containing cyclohexane-in-water emulsions stabilised by particles of Ce0.495Sn0.4...
Figure 5: Optical microscopy images of cyclohexane-in-water emulsions of Figure 4 after one month for particle concen...
Figure 6: (top) Mean emulsion droplet diameter after 30 min as a function of particle concentration for syste...
Figure 7: Mean particle diameter in aqueous dispersions as a function of Ce0.495Sn0.495Pd0.01O2–δ concentrati...
Figure 8: Variation of the zeta potential and pH value of aqueous dispersions of Ce0.495Sn0.495Pd0.01O2–δ par...
Figure 9: (a) Appearance of octane-in-water emulsions with time at 0.05 wt % of Ce0.495Sn0.495Pd0.01O2–δ (lef...
Figure 10: (a) Variation of droplet diameter with particle concentration for octane-in-water emulsions stabili...
Figure 11: (a) Variation of droplet diameter with particle concentration for toluene-in-water emulsions stabil...
Graphical Abstract
Scheme 1: SET-triggered Diels–Alder reaction of trans-anethole (1) and isoprene (2).
Figure 1: Plausible mechanism for the electrocatalytic Diels–Alder reaction. Adapted from [22].
Scheme 2: Undesired dimerization of trans-anethole (1).
Figure 2: GC–MS monitoring of the electrocatalytic Diels–Alder reaction (1: 300 mM; 2: 3000 mM).
Figure 3: GC–MS monitoring of the electrocatalytic Diels–Alder reaction (1: 1 mM; 2: 2000 mM).
Figure 4: GC–MS monitoring of the electrocatalytic Diels–Alder reaction (1: 2 M; 2: 6 M). Blue dots show the ...