Diastereoselective Mannich reactions of pseudo-C₂-symmetric glutarimide with activated imines

• Tatsuya Ishikawa,
• Tomoko Kawasaki-Takasuka,
• Toshio Kubota and
• Takashi Yamazaki

Beilstein J. Org. Chem. 2017, 13, 2473–2477, doi:10.3762/bjoc.13.244

• % yield as determined by 19F NMR (Table 1, entry 3). NaHMDS (Table 1, entry 4) or LiHMDS (Table 1, entry 5) instead of LDA worked properly affording 3a in a yield of 59 or 80%, respectively. The product 3a theoretically consists of 8 diastereomers and usually 2 isomers predominated with a couple of minor

Hydrolysis, polarity, and conformational impact of C-terminal partially fluorinated ethyl esters in peptide models

• Vladimir Kubyshkin and
• Nediljko Budisa

Beilstein J. Org. Chem. 2017, 13, 2442–2457, doi:10.3762/bjoc.13.241

• background in spectroscopic observations of biological samples. This feature is especially beneficial for NMR applications because the sole stable fluorine isotope (19F) has the third largest magnetogyric ratio among the nuclei measured by NMR (after 3H and 1H hydrogen isotopes); as a result, 19F NMR

• experiments are remarkably sensitive [4]. Fluorine-containing groups can be incorporated into biopolymers by various approaches, including those that utilize biosynthesis [5][6][7], enzymatic conversion [8], chemical synthesis [9][10], and ligation reactions [11]. Depending on the research target, 19F NMR

• abundant in the unfolded protein states [91]. Hydrolytic stability in peptides Finally, we tested hydrolytic stability in esterified peptides 8b, 9b and 10b by observing hydrolysis of the ester using 19F NMR in buffered deuterium oxide (pH 7). We expected pseudo-first order kinetics as for the hydrolysis

Homologated amino acids with three vicinal fluorines positioned along the backbone: development of a stereoselective synthesis

• Raju Cheerlavancha,
• Ahmed Ahmed,
• Yun Cheuk Leung,
• Aggie Lawer,
• Qing-Quan Liu,
• Marina Cagnes,
• Hee-Chan Jang,
• Xiang-Guo Hu and
• Luke Hunter

Beilstein J. Org. Chem. 2017, 13, 2316–2325, doi:10.3762/bjoc.13.228

• ketones [31]. However, 1H NMR and 19F NMR analysis of the crude reaction mixture revealed that the only identifiable product was the undesired gem-difluorinated compound 25 (Scheme 2), which was obtained along with a significant amount of unreacted starting material 21a (see Supporting Information File 1

• -scale final fluorination reaction was attempted (Scheme 3) because this was anticipated to converge some of the compounds into a simpler product mixture. Analysis of the crude reaction mixture by 19F NMR revealed that the desired product 29 may have been formed in small quantity. However, there was

• final compounds, which were of low molecular weight and very polar. Nevertheless, the first synthesis of a δ-amino acid containing three vicinal fluorines on the backbone had been successfully completed. The all-syn target 6b was then obtained in a similar fashion from 40b (Scheme 4). The 1H and 19F NMR

Comparative profiling of well-defined copper reagents and precursors for the trifluoromethylation of aryl iodides

• Peter T. Kaplan,
• Jessica A. Lloyd,
• Mason T. Chin and
• David A. Vicic

Beilstein J. Org. Chem. 2017, 13, 2297–2303, doi:10.3762/bjoc.13.225

• , we monitored the reactions of the iodotoluenes by quantitative 19F NMR spectroscopy. Using the same solvent systems employed for the reactions in Figure 2, conversions were measured over a 22 hour period (Figure 3). In this case, [(SIMes)Cu(CF3)] performed just as well as the [(phen)Cu(CF3

• by 1H NMR and 19F NMR for purity. Copper salt precursors were purchased from Sigma-Aldrich. Trimethyl(trifluoromethyl)silane (99% purity) was purchased from SynQuest Labs, Inc. and used without further purification. All other chemicals were verified by 1H NMR for purity and used without further

• glovebox. The quantitative NMR analyses were accomplished using a Bruker Ascend 400 MHz spectrometer by 19F NMR spectra referenced to internal standard of fluorobenzene. Solution 1H NMR spectra were recorded at ambient temperature on a Bruker Ascend 400 MHz spectrometer and referenced to residual proton

Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

• Satoru Mori and
• Norio Shibata

Beilstein J. Org. Chem. 2017, 13, 2273–2296, doi:10.3762/bjoc.13.224

• TFEO-ZnPc 4 and fluorinated polymer 22 were condensed by a click reaction between azide and alkyne groups (Scheme 8). The graft ratio of the TFEO-ZnPc-supported fluoropolymer was calculated from the area ratio of 19F NMR, and the resulting fluorinated copolymers showed different grafting ratios (from

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

• characterized by 1H, 11B, 13C and 19F NMR spectroscopy, mass spectrometry and elemental analysis. We found the complexes to possess high absorption in the range of 475 to 500 nm and strong fluorescence between 520 and 590 nm, resulting in Stokes shifts of up to 3000 cm−1. Finally, an effective strategy to

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

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

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

• , 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

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

• Hz, C-o), 131.9 (d, 4JC,F = 3.3 Hz, C-i), 163.5 (d, 1JC,F = 249.9 Hz, C-p), 169.5 (C=O); 19F NMR (376 MHz, CDCl3) δ −110.3; MS (ESI+) m/z (%): 261 (100) [M+ + H]; Anal. calcd for C15H17FN2O (260.31): C, 69.21; H, 6.58; N, 10.76; found, C, 68.99; H, 6.61; N, 10.80. 4-(3-Azidopropyl)-1-(4-nitrobenzoyl

• ), 131.9 (d, 4JC,F = 3.3 Hz, C-i), 163.5 (d, 1JC,F = 148.6 Hz, C-p), 163.5 (C=O); 19F NMR (376 MHz, CDCl3) δ −110.4; MS (ESI+) m/z (%): 292 (100) [M+ + H]; Anal. calcd for C14H18FN5O (291.32): C, 57.72; H, 6.23; N, 24.04; found, C, 57.90; H, 6.21; N, 24.24. SNEW-peptide (7): Azide-functionalized peptide 6

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

• –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

• concentrated using rotary evaporation of dichloromethane and poured into methanol (300 mL) to precipitate. The precipitate was filtered and washed with methanol and ether. After drying under vacuum overnight, the product was obtained as a dark blue solid (0.145 g, 78%). 19F NMR (470 MHz, CDCl3, δ) −92.35. L2

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

• (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