Highly regio- and stereoselective phosphinylphosphination of terminal alkynes with tetraphenyldiphosphine monoxide under radical conditions

• Dat Phuc Tran,
• Yuki Sato,
• Yuki Yamamoto,
• Shin-ichi Kawaguchi,
• Shintaro Kodama,
• Akihiro Nomoto and
• Akiya Ogawa

Beilstein J. Org. Chem. 2021, 17, 866–872, doi:10.3762/bjoc.17.72

• BioSpin Ascend 400 spectrometer (162 MHz). 19F NMR spectra were recorded on a Bruker BioSpin Ascend 400 spectrometer (377 MHz). IR spectra were recorded on JASCO FT/IR-680Plus instrument. High-resolution mass spectra (HRMS) were recorded on a Bruker micrOTOF II ESI(+)/TOF instrument. General procedure for

Chiral isothiourea-catalyzed kinetic resolution of 4-hydroxy[2.2]paracyclophane

• David Weinzierl and
• Mario Waser

Beilstein J. Org. Chem. 2021, 17, 800–804, doi:10.3762/bjoc.17.68

• ), 35.4 (1C, -CH2), 34.9 (1C, -CH2), 34.0 (1C, -CH2), 32.2 (1C, -CH2); HRMS (ESI) m/z: calcd for [C16H16O + H]+, 225.1274; found, 225.1280, HPLC: YMC Chiral ART Cellulose-SB, n-hexane/iPrOH 3:1, 1 mL/min, 10 °C; tR = 6.4 min [Sp; minor], 7.2 min [Rp; major]. (Sp)-3a: Analytical data match those reported

• (1C, -CH2), 35.0 (1C, -CH2), 34.4 (2C, -CH, -CH2), 31.8 (1C, -CH2), 19.4 (1C, -CH3), 19.1 (1C, -CH3); HRMS (ESI) m/z: calcd for [C20H22O2 + NH4]+, 312.1958; found, 312.1958, HPLC: YMC Chiral ART Cellulose-SB, n-hexane/iPrOH 3:1, 1 mL/min, 10 °C; tR = 7.3 min [Rp; minor], 8.4 min [Sp; major]. Overview

Designed whole-cell-catalysis-assisted synthesis of 9,11-secosterols

• Marek Kõllo,
• Marje Kasari,
• Villu Kasari,
• Tõnis Pehk,
• Ivar Järving,
• Margus Lopp,
• Arvi Jõers and
• Tõnis Kanger

Beilstein J. Org. Chem. 2021, 17, 581–588, doi:10.3762/bjoc.17.52

• 6540 UHD Accurate-Mass QTOF LC/MS spectrometer by using AJ-ESI as an ionization method. Construction of biocatalyst Plasmid cloning and amplification were performed in E. coli DH5 strain. E. coli strain BL21 (DE3) was used for biocatalysis experiments. Lysogeny broth (LB) medium was used for all cell

The synthesis of chiral β-naphthyl-β-sulfanyl ketones via enantioselective sulfa-Michael reaction in the presence of a bifunctional cinchona/sulfonamide organocatalyst

• Deniz Tözendemir and
• Cihangir Tanyeli

Beilstein J. Org. Chem. 2021, 17, 494–503, doi:10.3762/bjoc.17.43

• by chiral HPLC chromatography using Agilent instrument. All new products were further analyzed by LC/MS–HRMS–TOF or MALDI–ESI–TOFMS. Synthesis of organocatalyst 5 A solution of quinineamine 2 (226.40 mg, 0.70 mmol) and triethylamine (107 μL, 0.77 mmol) in CH2Cl2 was added to a screw-capped reaction

Synthesis of legonmycins A and B, C(7a)-hydroxylated bacterial pyrrolizidines

• Wilfred J. M. Lewis,
• David M. Shaw and
• Jeremy Robertson

Beilstein J. Org. Chem. 2021, 17, 334–342, doi:10.3762/bjoc.17.31

• pyrrole 18, and the appearance of new resonances at 3.21 (ddd, J = 11.5, 9.0, 2.5 Hz, 1H) and 3.64 (dt, J = 11.5, 8.5 Hz, 1H) ppm that correspond visually with those reported for the diastereotopic CH2N protons in legonmycin A. HRMS (ESI+) analysis of material isolated from this NMR experiment showed m/z

• , 36.2, 47.0 (three peaks), 63.3, 63.8, 64.5, 64.7, 80.5, 80.9, 81.0, 81.1, 117.8, 118.0, 118.1, 154.7, 155.4, 200.6 (two peaks), 201.0, 201.6; HRMS–ESI+ (m/z): [M + Na]+ calcd for C13H20N2O3Na, 275.1366; found, 275.1366. (S)-3-Amino-2-methyl-5,6,7,7a-tetrahydro-1H-pyrrolizin-1-one hydrochloride (17

• = 10.0, 8.5, 2.5 Hz, 1H), 4.44 (dd, J = 10.5, 5.5 Hz, 1H); 13C NMR (100 MHz, CD3OD) δ 5.8, 28.4, 30.2, 46.5, 70.0, 101.3 (from a separate spectrum of a stronger but impure sample), 174.4, 176.7; HRMS–ESI+ (m/z): [M]+ calcd for C8H13N2O, 153.1022; found, 153.1022. The free-base was also prepared in a

Hydrazides in the reaction with hydroxypyrrolines: less nucleophilicity – more diversity

• Dmitrii A. Shabalin,
• Evgeniya E. Ivanova,
• Igor A. Ushakov,
• Elena Yu. Schmidt and
• Boris A. Trofimov

Beilstein J. Org. Chem. 2021, 17, 319–324, doi:10.3762/bjoc.17.29

• Center for collective use SB RAS. ESI-HRMS-TOF spectra were recorded at Shared Research Facilities for Physical and Chemical Ultramicroanalysis, Limnological Institute, SB RAS. Funding The reported study was funded by RFBR according to the research project No. 18-33-00089.

1,2,3-Triazoles as leaving groups in S_NAr–Arbuzov reactions: synthesis of C6-phosphonated purine derivatives

• Kārlis-Ēriks Kriķis,
• Irina Novosjolova,
• Anatoly Mishnev and
• Māris Turks

Beilstein J. Org. Chem. 2021, 17, 193–202, doi:10.3762/bjoc.17.19

• , 75.5 MHz) δ 154.3 (D, 3JC–P = 11.7 Hz), 154.2 (D, 3JC–P = 7.7 Hz), 152.5 (D, 1JC–P = 203.6 Hz), 147.5, 134.3 (D, 2JC–P = 21.4 Hz), 64.2 (D, 2JC–P = 6.1 Hz), 44.2, 31.5, 29.8, 28.6, 26.5, 22.5, 16.4 (D, 3JC–P = 6.2 Hz), 14.4; 31P NMR (CDCl3, 121 MHz) δ 5.3; HRMS-ESI (m/z): [M + H]+ calcd for

• -ESI (m/z): [M + H]+ calcd for C20H25N10O4, 469.2055; found, 469.2022. General procedure for the SNAr–Arbuzov reaction: synthesis of 9-alkyl-2-triazolyl-9H-purine C6-phosphonates 4 Methyl 1-(6-(diethoxyphosphoryl)-9-heptyl-9H-purin-2-yl)-1H-1,2,3-triazole-4-carboxylate (4a): Dimethyl 1,1'-(9-heptyl-9H

• , CDCl3) δ 160.9, 154.0 (D, 3JC–P = 11.1 Hz), 152.4 (D, 1JC–P = 220.6 Hz), 148.6, 148.3 (D, 3JC–P = 23.4 Hz), 140.3, 135.3 (D, 2JC–P = 20.8 Hz), 127.4, 64.5 (D, 2JC–P = 6.2 Hz), 52.6, 44.6, 31.6, 29.9, 28.7, 26.7, 22.7, 16.6 (D, 3JC–P = 5.9 Hz), 14.1; 31P NMR (202 MHz, CDCl3) δ 5.3; HRMS-ESI (m/z): [M + H

Control over size, shape, and photonics of self-assembled organic nanocrystals

• Chen Shahar,
• Yaron Tidhar,
• Yunmin Jung,
• Haim Weissman,
• Sidney R. Cohen,
• Ronit Bitton,
• Iddo Pinkas,
• Gilad Haran and
• Boris Rybtchinski

Beilstein J. Org. Chem. 2021, 17, 42–51, doi:10.3762/bjoc.17.5

• applicability of organic nanocrystals. Experimental General information The 1H and 13C NMR spectra were recorded at 20 °C on a 300 MHz NMR spectrometer (Bruker). Electrospray ionization (ESI) mass spectrometry was performed using a Micromass Platform instrument. UV–vis absorption and fluorescence measurements

Naphthalonitriles featuring efficient emission in solution and in the solid state

• Sidharth Thulaseedharan Nair Sailaja,
• Iván Maisuls,
• Jutta Kösters,
• Alexander Hepp,
• Andreas Faust,
• Jens Voskuhl and
• Cristian A. Strassert

Beilstein J. Org. Chem. 2020, 16, 2960–2970, doi:10.3762/bjoc.16.246

• characterization of H – NMe2 and its aggregates. 1H NMR, 13C NMR and EM-ESI-MS spectra of all the six compounds. Supporting Information File 404: Experimental procedures, NMR and EM-ESI-MS spectra. Acknowledgements We thankfully acknowledge Lic. Matias E. Gutierrez Suburu for his assistance with the DLS

Synthesis and investigation of quadruplex-DNA-binding, 9-O-substituted berberine derivatives

• Jonas Becher,
• Daria V. Berdnikova,
• Heiko Ihmels and
• Christopher Stremmel

Beilstein J. Org. Chem. 2020, 16, 2795–2806, doi:10.3762/bjoc.16.230

• the corresponding solvent [δ(DMSO-d5) = 2.50 (1H) and 39.5 (13C); δ(CHCl3) = 7.26 (1H) and 77.2 (13C)]. Elemental analyses data were determined with a HEKAtech EURO EA combustion analyzer by Mr. Rochus Breuer (Organic Chemistry I, University of Siegen). Mass spectra (ESI) were recorded on a Finnigan

Ring-closing metathesis of prochiral oxaenediynes to racemic 4-alkenyl-2-alkynyl-3,6-dihydro-2H-pyrans

• Viola Kolaříková,
• Markéta Rybáčková,
• Martin Svoboda and
• Jaroslav Kvíčala

Beilstein J. Org. Chem. 2020, 16, 2757–2768, doi:10.3762/bjoc.16.226

• internal standards. Chemical shifts are given in parts per million and coupling constants in hertz. Mass spectra (ESI, APCI) and HRMS spectra were measured with a hybrid LTQ Obitrap XL instrument (Thermo Fisher Scientific). All reactions were performed in a dry inert atmosphere (Ar) in oven-dried flasks

• ), 129.0 (s, 1C, CH3-C=C), 129.1 (s, 2C, CHAr), 131.9 (s, 1C, CAr), 176.8 (s, 1C, CH-CH-C=O), 178.5 (s, 1C, CH2-CH-C=O); MS (ESI+, m/z) (%): 372.2 [M + Na]+ (100), 350.2 [M + H]+ (20); HRMS (ESI+, m/z): [M + H]+ calcd for C22H24O3N, 350.1751; found, 350.1752; HRMS (ESI+, m/z): [M + Na]+ calcd for

• ), 128.5 (s, 1C, CHAr), 129.1 (s, 2C, CHAr), 131.8 (s, 1C, CAr), 177.0 (s, 1C, CH-CH-C=O), 178.5 (s, 1C, CH2-CH-C=O); MS (ESI+, m/z): 372.2 [M + Na]+ (100), 350.2 [M + H]+ (35); HRMS (ESI+, m/z): [M + H]+ calcd for C22H24O3N, 350.1751; found, 350.1752; HRMS (ESI+, m/z): [M + Na]+ calcd for C22H23O3NNa

A heterobimetallic tetrahedron from a linear platinum(II)-bis(acetylide) metalloligand

• Matthias Hardy,
• Marianne Engeser and
• Arne Lützen

Beilstein J. Org. Chem. 2020, 16, 2701–2708, doi:10.3762/bjoc.16.220

• diastereomers. The new complexes were characterized by NMR and UV–vis spectroscopy and ESI mass spectrometry. Using GFN2-xTB we generated energy-minimized models of the diastereomers of this cage that further corroborated the results from analytical findings. Keywords: cage compounds; heterobimetallic

• amine functions and thus a higher tendency to undergo one-electron oxidation reactions when stored under ambient conditions. In order to check the composition of heterobimetallic 4 we performed mass spectrometric experiments first. Figure 1 shows the ESI mass spectrum of metallosupramolecular cage 4

• , showing a series of signals with different charge states that could be assigned to 4. The mass spectrum also shows that the cage easily fragments upon ESI, as additional signals a–d were detected. The successful formation of iron(II)-containing metallosupramolecular tetrahedron 4 could also be proven by

Synthesis of 4-substituted azopyridine-functionalized Ni(II)-porphyrins as molecular spin switches

• Jannis Ludwig,
• Tobias Moje,
• Fynn Röhricht and
• Rainer Herges

Beilstein J. Org. Chem. 2020, 16, 2589–2597, doi:10.3762/bjoc.16.210

• spectra. Acknowledgements We thank Dr. Florian Gutzeit for providing the substance for reference measurements (maximum shift of a fivefold coordinated Ni complex) and Nils Preußke for ESI measurements of compound 1h. Funding This work was funded by the Deutsche Forschungsgemeinschaft (DFG) within the

Water-soluble host–guest complexes between fullerenes and a sugar-functionalized tribenzotriquinacene assembling to microspheres

• Si-Yuan Liu,
• Xin-Rui Wang,
• Man-Ping Li,
• Wen-Rong Xu and
• Dietmar Kuck

Beilstein J. Org. Chem. 2020, 16, 2551–2561, doi:10.3762/bjoc.16.207

• ppm in the 13C NMR spectrum were attributed to the acetylene protons and carbons, respectively. The electrospray ionization (ESI) mass spectrum showed the most intense peak at m/z 641.1923, which corresponds to the [M + Na]+ molecular adduct ion and matches well with the calculated value (m/z 641.1935

• mass spectrum also shows the characteristic losses of up to at least three tentacle residues from both the [M + Na]+ and [M + K]+ molecular ions [44][45][46]. In contrast to the MALDI mass spectrum, the high-resolution ESI-(+) mass spectrum of TBTQ-(OAcG)6 (see Figure S11 and Table S2) exhibits a sole

• loss of the entire tentacle as an C9H14N3O5· radical (244 u) from the [M + Na]+ ion followed by H atom transfer. Again, accurate mass measurements were not obtained. As another surprise, the high-resolution ESI-(−) mass spectrum of TBTQ-(OG)6 (see Figure S15 and Table S4, Supporting Information File 1

Synthesis of 1,4-benzothiazinones from acylpyruvic acids or furan-2,3-diones and o-aminothiophenol

• Ekaterina E. Stepanova,
• Maksim V. Dmitriev and
• Andrey N. Maslivets

Beilstein J. Org. Chem. 2020, 16, 2322–2331, doi:10.3762/bjoc.16.193

• approach, we repeated some experiments described previously [27][28] and examined the reaction mixtures by UPLC–UV–MS. We supposed that the peak of the target BTA III would be characterized by appropriate molecular ion signals at ESI+ and ESI− chromatograms and absorbance bands at 400–450 nm

Naphthalene diimide–amino acid conjugates as novel fluorimetric and CD probes for differentiation between ds-DNA and ds-RNA

• Annike Weißenstein,
• Myroslav O. Vysotsky,
• Ivo Piantanida and
• Frank Würthner

Beilstein J. Org. Chem. 2020, 16, 2032–2045, doi:10.3762/bjoc.16.170

• Avance 400 spectrometer. The chemical shifts are reported in ppm and refer to the residual proton signal of the solvent as internal standard. Signal multiplicities are denoted as s (singlet), d (doublet), t (triplet), and m (multiplet). High-resolution ESI-TOF mass spectrometry was carried out on a

• , 18H), 2.14 (m, 4H); 13C NMR (DMSO-d6, 101 MHz) 161.1, 160.7, 137.6, 134.1, 127.0, 126.3, 122.5, 63.2, 52.2, 37.7, 21.4; HRMS-ESI+ (methanol, m/z): [M]2+ calcd for C26H32Cl2N4O4, 267.0900; found, 267.0900; UV–vis (MeOH) λ [nm] (ε [M−1 cm−1]) 397 (10300), 377 (10900), 357 (16000). Synthesis of (S)-N,N

• , 53.7, 53.7, 53.6, 53.5, 43.6, 39.0, 38.4, 23.2, 23.1; HRMS-ESI+ (methanol, m/z): [M]2+ calcd for C29H39ClN6O6, 301.1310; found, 301.1317; UV–vis (cacodylate buffer, pH 5.0) λ [nm] (ε [M−1 cm−1]) 519 (9100), 369 (9400), 351 (7500), 333 (5000); fluorescence (cacodylate buffer, pH 5.0, λex = 470 nm): λmax

Regiodivergent synthesis of functionalized pyrimidines and imidazoles through phenacyl azides in deep eutectic solvents

• Paola Vitale,
• Luciana Cicco,
• Ilaria Cellamare,
• Filippo M. Perna,
• Antonio Salomone and
• Vito Capriati

Beilstein J. Org. Chem. 2020, 16, 1915–1923, doi:10.3762/bjoc.16.158

• mass spectrometer equipped with an electrospray ion source (ESI). NaN3, 2-haloketones, and all other reagents, unless otherwise specified, were purchased from Sigma-Aldrich (Sigma-Aldrich, St. Louis, MO, USA), and used without any further purification. Experimental procedures General procedure for the

One-pot synthesis of oxazolidinones and five-membered cyclic carbonates from epoxides and chlorosulfonyl isocyanate: theoretical evidence for an asynchronous concerted pathway

• Esra Demir,
• Ozlem Sari,
• Yasin Çetinkaya,
• Ufuk Atmaca,
• Safiye Sağ Erdem and
• Murat Çelik

Beilstein J. Org. Chem. 2020, 16, 1805–1819, doi:10.3762/bjoc.16.148

• −1): 3251, 2928, 2863, 1805, 1410, 1358, 1210, 1175, 1034; anal. calcd for: C, 63.88; H, 8.93; N, 8.28; found: 63.56; H, 9.04; N, 8.54; HRMS–ESI (m/z): [M + H]+ calcd for C9H15NO2+, 169,1097; found, 169,1086. 3a,4,9,9a-Tetrahydro-4,9-methanonaphtho[2,3-d][1,3]dioxol-2-one (8i): Colourless solid, Rf

• , cm−1): 2932, 1804, 1460, 1160, 1066, 976; anal. calcd for: C, 71.28; H, 4.98; found: C, 71.43; H, 4.73; HRMS–ESI (m/z): [M + H]+ calcd for C12H10O3+, 202,0624; found, 202,0637. 3a,4,9,9a-Tetrahydro-4,9-methanonaphtho[2,3-d]oxazol-2(3H)-one (9i): Colourless solid, Rf = 0.3 (EtOAc/hexanes, 1:5); mp 133

• (CH2); IR (CHCl3, cm−1): 3340, 2918, 1802, 1647, 1461, 1368, 1166, 1001; anal. calcd for: C, 71.63; H, 5.51; N, 6.96; found: C, 71.48; H, 5.72; N, 6.79; HRMS–ESI (m/z): [M + H]+ calcd for C12H11NO2+, 201,0784; found, 201,0796. 3a-Phenylhexahydrobenzo[d][1,3]dioxol-2-one (8j): Colourless solid, Rf = 0.4

Synthesis of new dihydroberberine and tetrahydroberberine analogues and evaluation of their antiproliferative activity on NCI-H1975 cells

• Giacomo Mari,
• Lucia De Crescentini,
• Serena Benedetti,
• Francesco Palma,
• Stefania Santeusanio and
• Fabio Mantellini

Beilstein J. Org. Chem. 2020, 16, 1606–1616, doi:10.3762/bjoc.16.133

• elemental analysis. Mass spectra were recorded in the ESI and EI modes. The nomenclature was generated using ACD/IUPAC Name (version 3.50, 5 Apr. 1998), Advanced Chemistry Development Inc., Toronto, ON (Canada). General procedure for the synthesis of hydrazono-dihydroberberines (DHBERs) 2a–n. To a solution

• ), 108.1 (d), 110.2 (d), 125.2 (d), 126.0 (d), 127.4 (d), 127.8 (s), 128.0 (d), 128.4 (s), 128.7 (s), 129.1 (s), 138.2 (s), 143.8 (s), 145.7 (s), 146.3 (s), 148.9 (s), 150.1 (s), 152.3 (s); IR (nujol): νmax = 3288, 3129, 1742 cm−1; HRMS–ESI (m/z): [M + H]+: calcd. for C33H38N3O6, 572.2761; found, 572.2814

Antibacterial scalarane from Doriprismatica stellata nudibranchs (Gastropoda, Nudibranchia), egg ribbons, and their dietary sponge Spongia cf. agaricina (Demospongiae, Dictyoceratida)

• Cora Hertzer,
• Stefan Kehraus,
• Nils Böhringer,
• Fontje Kaligis,
• Robert Bara,
• Dirk Erpenbeck,
• Gert Wörheide,
• Till F. Schäberle,
• Heike Wägele and
• Gabriele M. König

Beilstein J. Org. Chem. 2020, 16, 1596–1605, doi:10.3762/bjoc.16.132

• residual solvent signals with resonances at δH/C 7.26/77.00 ppm (CDCl3). Mass spectra were recorded on a micrOTOF-Q mass spectrometer (Bruker) with ESI-source coupled with an HPLC Dionex Ultimate 3000 (Thermo Scientific) using an Agilent Zorbax Eclipse Plus C18 column (2.1 × 50 mm, 1.8 µm) at a temperature

A dynamic combinatorial library for biomimetic recognition of dipeptides in water

• Florian Klepel and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2020, 16, 1588–1595, doi:10.3762/bjoc.16.131

• compounds could not be achieved due to the high complexity of the library and the structural similarity of its members. Hence ESI-TOF mass spectrometry data can be interpreted qualitatively but not quantitatively. A full reference sample is shown in Figure 1. Each chromatogram represents a single

Five-component, one-pot synthesis of an electroactive rotaxane comprising a bisferrocene macrocycle

• Natalie Lagesse,
• Luca Pisciottani,
• Maxime Douarre,
• Pascale Godard,
• Brice Kauffmann,
• Vicente Martí-Centelles and
• Nathan D. McClenaghan

Beilstein J. Org. Chem. 2020, 16, 1564–1571, doi:10.3762/bjoc.16.128

• an FD emitter with an emitter voltage of 10 kV. The sample (1–2 µL) was deposited on a 13 μm emitter wire. Electrospray spectra (ESI) were recorded on a Qexactive (Thermo) mass spectrometer. The instrument was equipped with an ESI source and spectra were recorded in the positive mode. The spray

• , 51%). 1H NMR (300 MHz, CDCl3) δ 7.41–7.32 (m, 8H, Ph), 7.32–7.23 (m, 12H, Ph), 4.67 (d, J = 7.6 Hz, 4H, CH), 4.40 (t, J = 7.6 Hz, 2H, OCH2CH), 2.50 (s, 4H, CH2); 13C NMR (75 MHz, CDCl3) δ 172.1, 141.1, 128.6, 128.3, 126.9, 66.9, 49.8, 29.1; HRMS–ESI (m/z): [M + Na]+ calcd for C32H30O4Na, 501.20363

Synthesis of 3-substituted isoxazolidin-4-ols using hydroboration–oxidation reactions of 4,5-unsubstituted 2,3-dihydroisoxazoles

• Lívia Dikošová,
• Júlia Laceková,
• Ondrej Záborský and
• Róbert Fischer

Beilstein J. Org. Chem. 2020, 16, 1313–1319, doi:10.3762/bjoc.16.112

• NMR (150 MHz, CDCl3) δ 60.3 (PhCH2), 73.8 (C-5), 79.5 (C-3), 83.5 (C-4), 127.4 (CH-Ph), 127.9 (CH-Ph), 128.2 (CH-Ph), 128.3 (CH-Ph), 2×128.9 (CH-Ph), 137.4 (C-Ph), 138.2 (C-Ph); HRMS (ESI) (m/z): [M + H]+ calcd for C16H18NO2, 256.1333; found 256.1329. Typical procedure for the oxidation of

• (CH-Ph), 129.0 (CH-Ph), 129.2 (CH-Ph), 134.4 (C-Ph), 137.3 (C-Ph); HRMS (ESI) (m/z): [M + H]+ calcd for C16H18NO2, 256.1333; found 256.1329. N-Debenzylation with 2,2,2-trichloroethyl chloroformate (±)-2,2,2-Trichloroethyl 4-(benzoyloxy)-3-isopropylisoxazolidine-2-carboxylate (11): 2,2,2-Trichloroethyl

• ), 129.7 (CH-Ph), 133.7 (CH-Ph), 157.1 (CO2CH2), 165.9 (COPh); HRMS (ESI) (m/z): [M + H]+ calcd for C16H19Cl3NO5, 410.0324; found 410.0329. Hydrolysis of trichloroethyl carbamate (±)-3-Isopropylisoxazolidin-4-ol (12): The NaOH solution (0.6 mL, 3.6 mmol, 6 M) was added to a solution of the N-Troc

Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore

• Esteban P. Urriolabeitia,
• Pablo Sánchez,
• Alexandra Pop,
• Cristian Silvestru,
• Eduardo Laga,
• Ana I. Jiménez and
• Carlos Cativiela

Beilstein J. Org. Chem. 2020, 16, 1111–1123, doi:10.3762/bjoc.16.98

• silica gel (pore size 60 Å, 70–230 mesh, 63–200 μm) was used for gravity column chromatography. C, H, N and S elemental microanalyses were carried out on a Perkin-Elmer 2400-B Series II Analyzer. High-resolution mass spectra-ESI (HRMS-ESI) were recorded using a Bruker MicroToF-Q™ equipped with an API-ESI

• ), 130.1 (d, 4JCF = 3.4 Hz, C, C6H4F), 129.9 (d, 5JCF = 1.6 Hz, =CH, Cvin), 129.3 (s, CH, Cm, C6H5), 128.3 (s, CH, Co, C6H5), 116.3 (d, 2JCF = 22.3 Hz, CH, C6H4F), 113.4 (s, CH, =Cα); 19F NMR (282.40 MHz, CDCl3) δ −106.71 (tt, J = 8.5, 5.6 Hz); HRMS (ESI+) m/z: [M + Na]+: calcd for C18H12FNNaO2, 316.0750

• ', C6H3F). HRMS (ESI+) m/z: [M − COOCF3 + CH3O + Na]+ calcd. for, C38H28F2N2NaO6Pd2 882.9887; found, 882.9908; IR (ν, cm−1): 1791 (νC=O), 1653 (νC=N), 1190 (νCF3). General synthesis of the ortho-palladated cyclobutanes 4a–f, 4h–j The ortho-palladated dimers 3 (amount specified in each case) were suspended

Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties

• Nuray Altinolcek,
• Ahmet Battal,
• Mustafa Tavasli,
• William J. Peveler,
• Holly A. Yu and
• Peter J. Skabara

Beilstein J. Org. Chem. 2020, 16, 1066–1074, doi:10.3762/bjoc.16.93

• system. The IR spectra were obtained (4000–400 cm−1) using a Shimadzu IRAffinity-1S Fourier transform infrared spectrophotometer. The mass spectra were obtained by Bruker microTOFq mass spectrometers to obtain low- and high-resolution spectra using electron ionisation (EI) or electrospray ionisation (ESI