Curcuminoid–BF₂ complexes: Synthesis, fluorescence and optimization of BF₂ group cleavage

• Henning Weiss,
• Jeannine Reichel,
• Helmar Görls,
• Kilian Rolf Anton Schneider,
• Mathias Micheel,
• Michael Pröhl,
• Michael Gottschaldt,
• Benjamin Dietzek and
• Wolfgang Weigand

Beilstein J. Org. Chem. 2017, 13, 2264–2272, doi:10.3762/bjoc.13.223

• water. Because most of the compounds were partially hydrolysed when heated to 80 °C in aqueous acetone solution, we carried out the purification at room temperature. The final compounds were characterized by 1H, 11B{1H}, 13C{1H} and 19F{1H} NMR spectroscopy, EI mass spectrometry, elemental analyses as

• well as UV–vis absorption and fluorescence spectroscopy. The proton NMR spectra of all compounds exhibit the characteristic AB spin systems (J = approx. 16 Hz) occurring from the trans-olefinic protons in combination with a singlet at around 6.5 ppm. Signals in 19F{1H} NMR appeared as sharp singlets at

• around −140 ppm, while 11B{1H} NMR signals appear as up to 3 ppm broad singlets at about +0.9 ppm. No coupling between 19F and 11B nuclei was observed because of the high quadrupole moment of the 11B nucleus. Due to the high relative mass difference between both naturally occurring boron isotopes

Preparation of imidazo[1,2-a]-N-heterocyclic derivatives with gem-difluorinated side chains

• Layal Hariss,
• Kamal Bou Hadir,
• Mirvat El-Masri,
• Thierry Roisnel,
• René Grée and
• Ali Hachem

Beilstein J. Org. Chem. 2017, 13, 2115–2121, doi:10.3762/bjoc.13.208

• , 4J = 1.1 Hz), 128.8, 128.7 (2C), 128.5 (2C), 128.3 (2C), 126.5, 126.3, 125.9, 114.1 (t, 1J = 233.4 Hz), 87.0 (t, 3J = 6.8 Hz), 79.1 (t, 2J = 40.9 Hz), 64.0 (t, 4J = 1.8 Hz), 40.8 (t, 2J = 26.1 Hz), 28.9 (t, 3J = 4.0 Hz); 19F NMR (CDCl3, 282 MHz) δ −83.45 (td, JFH = 14.6, 3.9 Hz); HRMS (ESI) m/z [M

• (4 mL), then DBU (0.42 mL, 2.82 mmol, 1.5 equiv) was added and the reaction mixture was stirred at room temperature. After 2 h, 19F NMR showed 100% conversion and the reaction mixture was neutralized with a saturated solution of NH4Cl. After extraction with ethyl acetate, the organic phases were

• = 240.4 Hz), 38.9 (t, 2J = 25.9 Hz), 28.2 (t, 3J = 4.3 Hz); 19F NMR (CDCl3, 282 MHz) δ −98.84 (m); HRMS (ESI) m/z [M + Na]+: calcd. for C18H16OF2Na, 309.10614; found, 309.1059 (1 ppm). Synthesis of (2-(1,1-difluoro-3-phenylpropyl)imidazo[1,2-a]pyridin-3-yl)(phenyl)methanone (7a) A mixture of 2

One-pot multistep mechanochemical synthesis of fluorinated pyrazolones

• Joseph L. Howard,
• William Nicholson,
• Yerbol Sagatov and
• Duncan L. Browne

Beilstein J. Org. Chem. 2017, 13, 1950–1956, doi:10.3762/bjoc.13.189

• electron-withdrawing trifluoromethyl substituent was an exception to this (7) [31]. For this case, crude 19F NMR after the first step shows a 41% conversion, suggesting that the pyrazolone formation is the limiting factor in this example. An alkyl β-ketoester (ethyl acetoacetate) was also used, affording

Conformational impact of structural modifications in 2-fluorocyclohexanone

• Francisco A. Martins,
• Josué M. Silla and
• Matheus P. Freitas

Beilstein J. Org. Chem. 2017, 13, 1781–1787, doi:10.3762/bjoc.13.172

• 1H and TFA for 19F) in vacuum. Supporting Information Supporting Information File 158: Computational data. Acknowledgements The authors are thankful to CNPq, CAPES and FAPEMIG for the financial support of this research, as well as for the scholarship (to F.A.M.) and fellowships (to J.M.S. and M.P.F.).

1-Imidoalkylphosphonium salts with modulated C_α–P⁺ bond strength: synthesis and application as new active α-imidoalkylating agents

• Jakub Adamek,
• Roman Mazurkiewicz,
• Anna Węgrzyk and
• Karol Erfurt

Beilstein J. Org. Chem. 2017, 13, 1446–1455, doi:10.3762/bjoc.13.142

• , 31P and 19F NMR spectroscopy, as well as IR spectroscopy and HRMS spectrometry. Next the phosphonium salts were used in the Tscherniac–Einhorn–type imidoalkylation of aromatic hydrocarbons of diverse reactivity. The reaction was carried out without a catalyst, using a considerable excess of the

• ). 1H and 13C NMR spectra were recorded at operating frequencies of 400 and 100 MHz, respectively, using TMS as internal standard. 31P and 19F NMR spectra were recorded at operating frequencies of 161.9 and 376 MHz, respectively, without the resonance shift standard, with respect to H3PO4 and CFCl3

• mass and composition for the molecular ion adducts were calculated using the MassLynx software incorporated within the instrument. Spectroscopic properties of all synthesized compounds as well as 1H NMR, 13C NMR, 31P NMR and 19F NMR spectra of all new compounds are given in Supporting Information File

Synthesis and enzymatic ketonization of the 5-(halo)-2-hydroxymuconates and 5-(halo)-2-hydroxy-2,4-pentadienoates

• Tyler M. M. Stack,
• William H. Johnson Jr. and
• Christian P. Whitman

Beilstein J. Org. Chem. 2017, 13, 1022–1031, doi:10.3762/bjoc.13.101

• comparable. Composition of the equilibrium mixture for 5b–d Dienols 5b–d were allowed to equilibrate in 100 mM Na2HPO4 buffer (final pH 6.8–7.2) in the presence of Pp 4-OT, and the identities of the components of the mixture were determined by 1H NMR spectroscopy. The 1H, 13C, and 19F NMR data are presented

• mixture stirred at ambient temperature for 16 h. The reaction mixture was filtered and the filtrate was adjusted to pH 1 by the addition of concentrated HCl. The precipitate was collected by filtration and crystallized in ethyl acetate (3c: 1.18 g and 3d: 1.56 g). The 1H, 13C, and 19F NMR data are

• azeotrope any water that is present in the methanol. The resulting solution was evaporated to dryness under reduced pressure at room temperature to yield the monoacid (5c or 5d). Titration with hexanes yields a sticky yellow solid (≈100 mg). The compounds are stored at −20 °C. The 1H, 13C, and 19F NMR data

Glyco-gold nanoparticles: synthesis and applications

• Federica Compostella,
• Olimpia Pitirollo,
• Alessandro Silvestri and
• Laura Polito

Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100

• [105]. In another recent study on the development of synthetic nanosystems as potential carbohydrate-based vaccine, GAuNPs were loaded with synthetic oligosaccharide fragments corresponding to the repeating units of S. pneumoniae (Pn) CPS type 19F and 14 [106]. This new approach has explored the effect

Synthesis of ribavirin 2’-Me-C-nucleoside analogues

• Fanny Cosson,
• Aline Faroux,
• Jean-Pierre Baltaze,
• Jonathan Farjon,
• Régis Guillot,
• Jacques Uziel and
• Nadège Lubin-Germain

Beilstein J. Org. Chem. 2017, 13, 755–761, doi:10.3762/bjoc.13.74

• (triazole), 128.6, 128.2, 127.7 (Ph), 100.8 (d, J = 190 Hz, C2), 82.2 (C4), 79.7 (d, J = 39 Hz, C1), 73.9 (d, J = 23 Hz, C3), 61.3 (C5), 53.0 (-CH2Ph), 17.2 (d, J = 26 Hz, CH3); 19F NMR (376.2 MHz, MeOD) −158.2 (m); HRMS calcd for C16H20FN4O4, 351.1469; found, 351.1468. Debenzylation proceeded in ethanol (5

• ), 101.2 (d, J = 174 Hz, C2), 81.5 (C4), 78.5 (d, J = 39 Hz, C1), 72.6 (d, J = 23 Hz, C3), 60.6 (C5), 16.3 (d, J = 26 Hz, CH3); 19F NMR (376.2 MHz, MeOD) −160.8 (m); HRMS calcd for C9H14FN4O4, 261.0999; found, 261.1006. Targeted compounds. Retrosynthesis of compound 1. X-ray spectrum of compound 10b

Fluorinated cyclohexanes: Synthesis of amine building blocks of the all-cis 2,3,5,6-tetrafluorocyclohexylamine motif

• Tetiana Bykova,
• Nawaf Al-Maharik,
• Alexandra M. Z. Slawin and
• David O'Hagan

Beilstein J. Org. Chem. 2017, 13, 728–733, doi:10.3762/bjoc.13.72

• with Et3N·3HF at 120 °C generated the tetrafluorocyclohexane 11a, the structure of which was confirmed by X-ray crystallography (Scheme 2). Although the conversion of 10a to 11a was high as judged by 19F NMR, the isolated yield was modest as the compound was volatile and sublimed easily under reduced

Substitution of fluorine in M[C₆F₅BF₃] with organolithium compounds: distinctions between O- and N-nucleophiles

• Anton Yu. Shabalin,
• Nicolay Yu. Adonin and
• Vadim V. Bardin

Beilstein J. Org. Chem. 2017, 13, 703–713, doi:10.3762/bjoc.13.69

• of many unknown products forms in which a small amount 2,3,5,6-tetrafluorotoluene (4) was identified. Treatment of these products with aqueous KF increased the content of 4 and led to the appearance of C6F5H and 2,3,4,5-tetrafluorotoluene (5) (19F NMR), which may be attributed to hydrodeboration of

• of these salts to 16, 17, 18 and 19, respectively. The molar ratio of the produced polyfluoroarenes is the same as the ratio of their organoboron precursors (Scheme 5). The 19F NMR spectrum of 17 was described [34] and the spectrum of 16 is closely related to the spectrum of known compound 4 [33

• ]. The structures of 18 and 19 are consistent with 19F NMR, GC–MS and HRMS data. For characterization of the products derived from 1-K and PhLi we performed the hydrodeboration of a mixture of 1-K, 10-K and 11-K by stirring it in 2-methoxyethanol under reflux. After evaporation of the alcohol and C6F5H

NMR reaction monitoring in flow synthesis

• M. Victoria Gomez and
• Antonio de la Hoz

Beilstein J. Org. Chem. 2017, 13, 285–300, doi:10.3762/bjoc.13.31

• [20]. Despite these disadvantages, interesting applications of planar microcoils can be found in literature. Hence, Velders et al. [25] studied supramolecular interactions by 19F NMR spectroscopy at the picomole level. This application takes advantage of the high sensitivity and large chemical-shift

• including DEPT spectra, 2D-NMR spectroscopy, 19F NMR spectroscopy and monitoring of the stereoselectivity in Diels–Alder reactions and self-optimization of flow conditions using a modified version of the Nelder–Mead algorithm. For the NMR integral data for each experiment, the algorithm (Figure 15) selects

New approaches to organocatalysis based on C–H and C–X bonding for electrophilic substrate activation

• Pavel Nagorny and
• Zhankui Sun

Beilstein J. Org. Chem. 2016, 12, 2834–2848, doi:10.3762/bjoc.12.283

• during the catalytic process was supported by 13C and 19F NMR studies. Halogen bond donor organocatalysis based on aryl halides The pioneering study of Bolm has attracted significant attention and a number of important studies have emerged since then. In particular, the Huber group has contributed to the

Organofluorine chemistry: Difluoromethylene motifs spaced 1,3 to each other imparts facial polarity to a cyclohexane ring

• Mathew J. Jones,
• Ricardo Callejo,
• Alexandra M. Z. Slawin,
• Michael Bühl and
• David O'Hagan

Beilstein J. Org. Chem. 2016, 12, 2823–2827, doi:10.3762/bjoc.12.281

• , showing a characteristic AB system in 19F NMR for axial/equatorial fluorines, and a triplet (1JCF = 250 Hz) in 13C NMR for the CF2 group. In addition, single crystal X-ray diffraction data were obtained for 4c which confirmed the structure (Figure 2). The C–CF2–C angles in the cyclohexane ring are

Electron-transfer-initiated benzoin- and Stetter-like reactions in packed-bed reactors for process intensification

• Anna Zaghi,
• Daniele Ragno,
• Graziano Di Carmine,
• Carmela De Risi,
• Olga Bortolini,
• Pier Paolo Giovannini,
• Giancarlo Fantin and
• Alessandro Massi

Beilstein J. Org. Chem. 2016, 12, 2719–2730, doi:10.3762/bjoc.12.268

• –400 mesh). 1H (300 MHz), 13C (101 MHz) and 19F (376 MHz) NMR spectra were recorded for CDCl3 solutions at room temperature unless otherwise specified. Peaks assignments were aided by 1H,1H COSY and gradient-HMQC experiments. For accurate mass measurements, the compounds were analyzed in positive ion

• , 1H, Ar), 7.21–7.05 (m, 2H, Ar); 13C{1H} NMR (101 MHz, CDCl3) δ 192.9, 165.9, 160.2 (d, J = 250 Hz), 134.4, 133.9, 133.5, 131.5 (d, J = 8.4 Hz), 130.1 (d, J = 2.5 Hz), 129.3, 129.0, 128.9, 128.7, 128.5, 125.0 (d, J = 3.3 Hz), 121.4 (d, J = 14 Hz), 116.3 (d, J = 22 Hz), 70.7; 19F NMR (376 MHz, CDCl3) δ

• ), 159.7, 151.2, 150.1, 149.1, 147.6, 137.0, 136.9, 131.2 (d, J = 8.4 Hz), 130.7 (d, J = 2.3 Hz), 127.7, 127.1, 125.70, 124.4 (d, J = 3.7 Hz), 122.9, 121.4 (d, J = 14 Hz), 116.2 (d, J = 22 Hz), 72.4; 19F NMR (376 MHz, CDCl3) δ −115.2 to −115.3 (m); HRMS–ESI/Q-TOF (m/z): [M + H]+ calcd for C19H14FN2O3

From betaines to anionic N-heterocyclic carbenes. Borane, gold, rhodium, and nickel complexes starting from an imidazoliumphenolate and its carbene tautomer

• Ming Liu,
• Jan C. Namyslo,
• Martin Nieger,
• Mika Polamo and
• Andreas Schmidt

Beilstein J. Org. Chem. 2016, 12, 2673–2681, doi:10.3762/bjoc.12.264

• (crystallographic numbering, cf. Figure 2: C9) is clearly detectable at δ = 9.22 ppm in DMSO-d6, while the boron and fluorine atoms give resonance frequencies at δ = −3.45 ppm, and δ = −133.91, −159.97, −165.18 ppm in the 11B NMR and 19F NMR spectra, respectively. A single crystal X-ray analysis of the borane

• (+, C-10), 117.4 (+, C-8), 48.7 (−,C-12), 31.4 (−, C-13), 18.6 (−, C-14), 13.0 (+, C-15) ppm; 11B NMR (DMSO-d6, 128 MHz, external reference) δ −3.45 ppm; 19F NMR (DMSO-d6, 565 MHz, Cl3CF) δ −133.91 (d, 3JF,F = 21.5 Hz, 6F, F-19/19'), −159.97 (t, 3JF,F = 21.5 Hz, 3F, F-21), −165.18 (dd, 3JF,F = 21.5 Hz

Biomimetic synthesis and HPLC–ECD analysis of the isomers of dracocephins A and B

• Viktor Ilkei,
• András Spaits,
• Anita Prechl,
• Áron Szigetvári,
• Zoltán Béni,
• Miklós Dékány,
• Csaba Szántay Jr,
• Judit Müller,
• Árpád Könczöl,
• Ádám Szappanos,
• Attila Mándi,
• Sándor Antus,
• Ana Martins,
• Attila Hunyadi,
• György Tibor Balogh,
• György Kalaus (†),
• Hedvig Bölcskei,
• László Hazai and
• Tibor Kurtán

Beilstein J. Org. Chem. 2016, 12, 2523–2534, doi:10.3762/bjoc.12.247

• uncorrected. IR spectra were recorded on a Bruker FTIR instrument. NMR measurements (1H, 13C, gCOSY, 1D NOESY and 2D NOESY, gHSQCAD, gHMBCAD) were performed on Varian 400 MHz (equipped with 5 mm OneNMR 15N-31P/{1H-19F} PFG Probe), Varian 500 MHz (equipped with 1H{13C/15N} 5 mm PFG Triple Resonance 13C

Synthesis, dynamic NMR characterization and XRD studies of novel N,N’-substituted piperazines for bioorthogonal labeling

• Constantin Mamat,
• Marc Pretze,
• Matthew Gott and
• Martin Köckerling

Beilstein J. Org. Chem. 2016, 12, 2478–2489, doi:10.3762/bjoc.12.242

• Novel, functionalized piperazine derivatives were successfully synthesized and fully characterized by 1H/13C/19F NMR, MS, elemental analysis and lipophilicity. All piperazine compounds occur as conformers resulting from the partial amide double bond. Furthermore, a second conformational shape was

• General information All chemicals were purchased from commercial suppliers and used without further purification unless otherwise specified. Anhydrous THF was purchased from Acros. NMR spectra of all compounds were recorded on an Agilent DD2-400 MHz NMR spectrometer. Chemical shifts of the 1H, 19F, and

• 13C spectra were reported in parts per million (ppm) using TMS as internal standard for 1H/13C and CFCl3 for 19F spectra. Mass spectrometric (MS) data were obtained on a Xevo TQ-S mass spectrometer (Waters) by electron spray ionization (ESI). The melting points were determined on a Galen III melting

Comparing blends and blocks: Synthesis of partially fluorinated diblock polythiophene copolymers to investigate the thermal stability of optical and morphological properties

• Pierre Boufflet,
• Sebastian Wood,
• Jessica Wade,
• Zhuping Fei,
• Ji-Seon Kim and
• Martin Heeney

Beilstein J. Org. Chem. 2016, 12, 2150–2163, doi:10.3762/bjoc.12.205

• non-fluorinated block occurs as a distinct triplet at 2.89 ppm, demonstrating the shielding effect of the ortho-fluorine. The 19F NMR (see Supporting Information File 1, Figures S1 and S2) shows a single peak in both cases, demonstrating that these polymers are indeed regioregular block copolymers

• and 19F NMR spectra were recorded on a Bruker AV-400 (400 MHz), using the residual solvent resonance of CDCl3 or d2-1,1,2,2-tetrachloroethane and are given in ppm. Number-average (Mn) and weight-average (Mw) were determined by Agilent Technologies 1200 series GPC running in chlorobenzene at 80 °C

• ) 7.05 (s, 1H), 2.94–2.85 (m, 1.8H), 2.85–2.77 (m, 0.9H), 1.90–1.66 (m, 3H), 1.56–1.35 (m, 15H), 1.03–0.90 (m, 4.2H); 19F NMR (376 MHz, TCE-d2, 403 K, δ) −122.94 (s). Synthesis of P3OT-b-F-P3OT 1:4 In a sealed dry 2–5 mL microwave vial charged with dichloro(1,3-bis(diphenylphosphino)propane)nickel (2.27

Superelectrophilic activation of 5-hydroxymethylfurfural and 2,5-diformylfuran: organic synthesis based on biomass-derived products

• Dmitry S. Ryabukhin,
• Dmitry N. Zakusilo,
• Mikhail O. Kompanets,
• Anton A.Tarakanov,
• Irina A. Boyarskaya,
• Tatiana O. Artamonova,
• Mikhail A. Khohodorkovskiy,
• Iosyp O. Opeida and
• Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2016, 12, 2125–2135, doi:10.3762/bjoc.12.202

• -HMF (1a) with arenes under the action of TfOH or acidic zeolite CBV-720. Reactions of 2,5-DFF 2 with arenes under the action of various acids. Supporting Information Supporting Information File 280: Experimental procedures, characterization of compounds, 1H, 13C, 19F NMR spectra, and data on DFT

Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics

• Forrest S. Etheridge,
• Roshan J. Fernando,
• Sandra Pejić,
• Matthias Zeller and
• Geneviève Sauvé

Beilstein J. Org. Chem. 2016, 12, 1925–1938, doi:10.3762/bjoc.12.182

• ][33][34]. (4-Fluorophenylethynyl)tributyltin (for the synthesis of L3), and [4-(trifluoromethyl)phenyl](tributyltin)acetylene (for the synthesis of L4) were synthesized according to literature procedures with minor modifications and used without purification [35][36]. Methods 1H, 19F, and 13C NMR

• –7.41 (t, J = 8 Hz, 4H), 7.38–7.35 (t, J = 8 Hz, 2H), 7.24–7.20 (t, J = 8 Hz, 4H), 7.13 (s, 2H)); 19F NMR (470 MHz, CDCl3) δ −92.35. L2-ADP: 4-Fluorochalcone (3.29 g, 13.26 mmol) was dissolved in methanol (100 mL) in a round-bottom flask (100 mL) connected with a reflux condenser. Then nitromethane

• ), 7.48 (t, J = 7.5 Hz, 2H), 7.16 (s, 2H), 7.12 (t, J = 7 Hz, 4H); 19F NMR (470 MHz, CDCl3) δ −113.37. L1-ADPI2: A similar procedure was used as for ADPI2 (0.550 g, 75%) [33]. 19F NMR (470 MHz, CDCl3) δ −92.35. L2-ADPI2: A similar procedure was used as for ADPI2 (0.998 g, 82%) [33]. MALDI–TOF–MS m/z

Rh-Catalyzed reductive Mannich-type reaction and its application towards the synthesis of (±)-ezetimibe

• Motoyuki Isoda,
• Kazuyuki Sato,
• Yurika Kunugi,
• Satsuki Tokonishi,
• Atsushi Tarui,
• Masaaki Omote,
• Hideki Minami and
• Akira Ando

Beilstein J. Org. Chem. 2016, 12, 1608–1615, doi:10.3762/bjoc.12.157

• NMR and 13C NMR spectra were recorded on JNM-GX400 spectrometers and ECZS-400 spectrometers. 19F NMR spectra were recorded on Hitachi FT-NMR R-90H spectrometers. Chemical shifts of 1H NMR and 13C NMR are reported in ppm from tetramethylsilane (TMS) as an internal standard. Chemical shifts of 19F NMR

One-pot synthesis of 4′-alkyl-4-cyanobiaryls on the basis of the terephthalonitrile dianion and neutral aromatic nitrile cross-coupling

• Roman Yu. Peshkov,
• Elena V. Panteleeva,
• Wang Chunyan,
• Evgeny V. Tretyakov and
• Vitalij D. Shteingarts

Beilstein J. Org. Chem. 2016, 12, 1577–1584, doi:10.3762/bjoc.12.153

• with ω-substituted-alkyl bromides 6a–f. Interaction of dianion 12– with cyanoarenes 2b–i, followed by alkylation of intermediate anions 3b–i with butyl bromide 6a. Supporting Information Supporting Information File 550: Experimental section and 1H, 13C and 19F NMR spectra of all synthesized compounds

Methylpalladium complexes with pyrimidine-functionalized N-heterocyclic carbene ligands

• Dirk Meyer and
• Thomas Strassner

Beilstein J. Org. Chem. 2016, 12, 1557–1565, doi:10.3762/bjoc.12.150

• complexes as well. Experimental 1H and 13C NMR spectra were obtained on a Bruker AC 300 P (1H: 300.1 MHz, 13C: 75.5 MHz, 19F: 282.4 MHz) or a Bruker DRX 500 (1H: 500.1 MHz, 13C: 125.8 MHz, 19F: 470.3 MHz) spectrometer at 298 K. Elemental analyses were performed by the microanalytical laboratory of our

• (CH3 iPr), 27.9 (CH iPr), 118.1 (p-CH pym), 120.4 (NCH), 123.7 (m-CH ph), 127.2 (NCH), 130.4 (p-CH ph), 131.7 (ipso-C ph), 144.3 (o-C ph), 156.2 (ipso-C pym), 162.1 (m-CH pym), carbene-C not observed; 19F NMR (DMSO-d6, 75.5 MHz, ppm) δ −72.54 (CF3), −73.47 (CF3); anal. calcd for C23H22F6N4O4Pd: C

Reactions of N,3-diarylpropiolamides with arenes under superelectrophilic activation: synthesis of 4,4-diaryl-3,4-dihydroquinolin-2(1H)-ones and their derivatives

• Larisa Yu. Gurskaya,
• Diana S. Belyanskaya,
• Dmitry S. Ryabukhin,
• Denis I. Nilov,
• Irina A. Boyarskaya and
• Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2016, 12, 950–956, doi:10.3762/bjoc.12.93

• , and 4a,b were determined by means of 1H, 13C, 19F NMR, HRMS methods (see Supporting Information File 1), and X-ray analysis in case of compound 2f (Figure 1). We found that the best conditions for the synthesis of dihydroquinolines 2 from amides 1 and arenes were as follows: TfOH, room temperature

• to dihydroquinolinones 2a–x. Selected electronic characteristics (DFT calculations) of dications C1 and D1 derived from protonation of 5a and 6a, respectively. Supporting Information Supporting Information File 110: Experimental procedures, characterization of compounds, 1H, 13C, 19F NMR spectra

Enantioselective carbenoid insertion into C(sp³)–H bonds

• J. V. Santiago and
• A. H. L. Machado

Beilstein J. Org. Chem. 2016, 12, 882–902, doi:10.3762/bjoc.12.87

• favored the S configuration at the generated stereogenic center for most of the prepared lactones. The opposite preference, R configuration at the new stereogenic center of 20, was reported to the use of the enantiomeric rhodium complex (R)-18. When substrate 19f reacts under catalysis of rhodium(II