Direct borylation of terrylene and quaterrylene

• Haruka Kano,
• Keiji Uehara,
• Kyohei Matsuo,
• Hironobu Hayashi,
• Hiroko Yamada and
• Naoki Aratani

Beilstein J. Org. Chem. 2020, 16, 621–627, doi:10.3762/bjoc.16.58

• -dioxane (5 mL) under Ar at 105 °C for 30 h gave a deep orange solution (Scheme 1). Matrix assisted laser desorption/ionization (MALDI) mass spectrometry of the reaction mixture detected a single parent ion peak at m/z = 880.4687 (calcd for C54H60B4O8 = 880.4660 [M]+), making us expect its selective tetra

• many uses in organic devices. Experimental 1H NMR (500 MHz) and 13C NMR (126 MHz) spectra were recorded with a JEOL JNM-ECX500 spectrometer at 20 °C by using tetramethylsilane as an internal standard. High-resolution mass spectra (HRMS) were measured with the matrix-assisted laser desorption/ionization

Halogen-bonding-induced diverse aggregation of 4,5-diiodo-1,2,3-triazolium salts with different anions

• Xingyu Xu,
• Shiqing Huang,
• Zengyu Zhang,
• Lei Cao and
• Xiaoyu Yan

Beilstein J. Org. Chem. 2020, 16, 78–87, doi:10.3762/bjoc.16.10

• electrospray ionization mode (ESI). Elemental analyses (C, H, N) were performed on Flash EA 1112 Analyzer. Synthesis 2-I: 4,5-Unsubstituted triazolium salt 1 (450 mg, 1 mmol), potassium tert-butoxide (250 mg, 2.2 mmol) and I2 (510 mg, 2 mmol) were added in a Schlenk tube under nitrogen, then THF (20 mL) was

Synthesis and characterization of bis(4-amino-2-bromo-6-methoxy)azobenzene derivatives

• David Martínez-López,
• Amirhossein Babalhavaeji,
• Diego Sampedro and
• G. Andrew Woolley

Beilstein J. Org. Chem. 2019, 15, 3000–3008, doi:10.3762/bjoc.15.296

• referenced to residual undeuterated solvent signals. Mass spectra were recorded using an Agilent 6538 mass spectrometer with a Q-TOF ionization source or a JEOL AccuTOF mass spectrometer with a DART ionization source. Synthesis and characterization 4-Chloro-2-methoxyanilinium chloride (7): (1) 2-Amino-5

Palladium-catalyzed Sonogashira coupling reactions in γ-valerolactone-based ionic liquids

• László Orha,
• József M. Tukacs,
• László Kollár and
• László T. Mika

Beilstein J. Org. Chem. 2019, 15, 2907–2913, doi:10.3762/bjoc.15.284

• File 1. Exact mass measurements were performed on a high-resolution Q-Exactive Focus hybrid quadrupole-orbitrap mass spectrometer (Thermo Fisher Scientific, Bremen, Germany) equipped with a heated electrospray ionization (ESI) source. Samples were dissolved in acetonitrile/water 1:1 (v/v) solvent

• mixture containing 0.1% (v/v) formic acid. Solutions were directly introduced into the ion source using a syringe pump. Under the applied conditions, the compounds form protonated molecules, [M + H]+ in positive ionization mode (ESI). Detailed experimental procedures, characterization data are reported in

Bacterial terpene biosynthesis: challenges and opportunities for pathway engineering

• Eric J. N. Helfrich,
• Geng-Min Lin,
• Christopher A. Voigt and
• Jon Clardy

Beilstein J. Org. Chem. 2019, 15, 2889–2906, doi:10.3762/bjoc.15.283

• structure predictions based on genome sequence information, and finally 3) low production titers of bacterial terpenoids under standard laboratory conditions. These factors, in combination with general terpene properties such as lack of UV-absorbing functional groups, poor ionization properties, and

Acid-catalyzed rearrangements in arenes: interconversions in the quaterphenyl series

• Sarah L. Skraba-Joiner,
• Carter J. Holt and
• Richard P. Johnson

Beilstein J. Org. Chem. 2019, 15, 2655–2663, doi:10.3762/bjoc.15.258

• through time-of-flight matrix assisted laser desorption ionization (MALDI–TOF–MS) mass spectrometry, using sulfur as a matrix. Suzuki–Miyaura coupling to form m,p’-quaterphenyl (13) [35]: 4-Biphenylboronic acid (0.18 g, 0.91 mmol) and 1 M K2CO3 (1.5 mL) were added to a 10 mL Pyrex microwave tube. 3

AgNTf₂-catalyzed formal [3 + 2] cycloaddition of ynamides with unprotected isoxazol-5-amines: efficient access to functionalized 5-amino-1H-pyrrole-3-carboxamide derivatives

• Ziping Cao,
• Jiekun Zhu,
• Li Liu,
• Yuanling Pang,
• Laijin Tian,
• Xuejun Sun and
• Xin Meng

Beilstein J. Org. Chem. 2019, 15, 2623–2630, doi:10.3762/bjoc.15.255

• ), d (doublet), dd (doublet of doublets), t (triplet), q (quartet), and m (multiplet). All melting points are uncorrected and determined on an X-4 digital microscopic melting point apparatus. HRMS were measured using electrospray ionization (ESI). Ynamide compounds 4a–q were prepared according to the

Anion-driven encapsulation of cationic guests inside pyridine[4]arene dimers

• Anniina Kiesilä,
• Jani O. Moilanen,
• Anneli Kruve,
• Christoph A. Schalley,
• Perdita Barran and
• Elina Kalenius

Beilstein J. Org. Chem. 2019, 15, 2486–2492, doi:10.3762/bjoc.15.241

• + formed complexes with 1 and 12, neither using electrospray ionization (ESI) in the positive nor the negative mode. Pr4N+ is certainly too large to fit inside the dimeric capsule, whereas the other non-complexing cations are protic and – as rather strong hydrogen-bond donors – may interfere with

Combining the Ugi-azide multicomponent reaction and rhodium(III)-catalyzed annulation for the synthesis of tetrazole-isoquinolone/pyridone hybrids

• Gerardo M. Ojeda,
• Prabhat Ranjan,
• Pavel Fedoseev,
• Lisandra Amable,
• Upendra K. Sharma,
• Daniel G. Rivera and
• Erik V. Van der Eycken

Beilstein J. Org. Chem. 2019, 15, 2447–2457, doi:10.3762/bjoc.15.237

• chromatographic solvents is presented as volume:volume ratios. Isolated compounds were submitted to HRMS using an Agilent 6220A Time of Flight MSD spectrometer equipped with an ESI ionization source. IR spectra were recorded on a Bruker Alpha FTIR spectrometer. Only frequencies (ν, in cm−1) of the most relevant

Current understanding and biotechnological application of the bacterial diterpene synthase CotB2

• Ronja Driller,
• Daniel Garbe,
• Norbert Mehlmer,
• Monika Fuchs,
• Keren Raz,
• Dan Thomas Major,
• Thomas Brück and
• Bernhard Loll

Beilstein J. Org. Chem. 2019, 15, 2355–2368, doi:10.3762/bjoc.15.228

• carbocation (3) and finally the quenching of the carbocation by a base or water [16][17]. TPSs can be divided into two distinct classes, which are distinguished by their substrate activation mechanism. Whereas ionization of an isoprenoid diphosphate is caused by hydrolysis of the pyrophosphate by a trinuclear

Azologization and repurposing of a hetero-stilbene-based kinase inhibitor: towards the design of photoswitchable sirtuin inhibitors

• Christoph W. Grathwol,
• Nathalie Wössner,
• Sören Swyter,
• Adam C. Smith,
• Enrico Tapavicza,
• Robert K. Hofstetter,
• Anja Bodtke,
• Manfred Jung and
• Andreas Link

Beilstein J. Org. Chem. 2019, 15, 2170–2183, doi:10.3762/bjoc.15.214

• ionization single quadrupole MS (LCMS-2020) controlled by Shimadzu LabSolution software (Version 5.91). Chromatographic purification of products was performed by flash chromatography on silica gel (20–45 µm, Carl Roth) applying pressured air up to 0.8 bar. NMR spectra were recorded on a Bruker Avance III

• apparatus from Büchi and are uncorrected. High accuracy mass spectra were recorded on a Shimadzu LCMS-IT-TOF using ESI ionization. Purity of final compounds was determined by HPLC with DAD (applying the 100% method at 220 nm). Preparative and analytical HPLC were performed using Shimadzu devices CBM-20A, LC

Synthesis and anion binding properties of phthalimide-containing corona[6]arenes

• Meng-Di Gu,
• Yao Lu and
• Mei-Xiang Wang

Beilstein J. Org. Chem. 2019, 15, 1976–1983, doi:10.3762/bjoc.15.193

• investigate their anion binding behaviour. Taking compound 3a as a representative, we examined the interaction of macrocycles 3 with anions of tetra-n-butylammonium salts by means of electron spray ionization (ESI) mass spectrometry. It was found that the mass spectra of mixed samples of 3a with n-Bu4NX gave

Synthesis of a [6]rotaxane with singly threaded γ-cyclodextrins as a single stereoisomer

• Jason Yin Hei Man and
• Ho Yu Au-Yeung

Beilstein J. Org. Chem. 2019, 15, 1829–1837, doi:10.3762/bjoc.15.177

• HKU Foundation Postgraduate Fellowship. We acknowledge UGC funding administered by The University of Hong Kong for support of the Electrospray Ionization Quadrupole Time-of-Flight Mass Spectrometry Facilities under support for Interdisciplinary Research in Chemical Science.

Complexation of 2,6-helic[6]arene and its derivatives with 1,1′-dimethyl-4,4′-bipyridinium salts and protonated 4,4'-bipyridinium salts: an acid–base controllable complexation

• Jing Li,
• Qiang Shi,
• Ying Han and
• Chuan-Feng Chen

Beilstein J. Org. Chem. 2019, 15, 1795–1804, doi:10.3762/bjoc.15.173

• -polar solvent, acetone hampers or competes the intermolecular non-covalent interactions between the hosts and the guests, and thus resulted in a decrease of the host–guest complexation. ESIMS studies of the formation of host–guest complexes The electrospray ionization (ESI) mass spectra also confirmed

Functional panchromatic BODIPY dyes with near-infrared absorption: design, synthesis, characterization and use in dye-sensitized solar cells

• Quentin Huaulmé,
• Cyril Aumaitre,
• Outi Vilhelmiina Kontkanen,
• David Beljonne,
• Alexandra Sutter,
• Gilles Ulrich,
• Renaud Demadrille and
• Nicolas Leclerc

Beilstein J. Org. Chem. 2019, 15, 1758–1768, doi:10.3762/bjoc.15.169

• ) Grafting the triphenylamine donor moieties on the thiophene-vinylene bridge only slightly (by ca. 0.1 eV) lowers the ionization potential of the dyes, compare (1,2) to (3,4); this is explained by the fact that the HOMO molecular orbital mostly spreads on the BODIPY-vinylthiophene core of the molecules

Synthesis, enantioseparation and photophysical properties of planar-chiral pillar[5]arene derivatives bearing fluorophore fragments

• Guojuan Li,
• Chunying Fan,
• Guo Cheng,
• Wanhua Wu and
• Cheng Yang

Beilstein J. Org. Chem. 2019, 15, 1601–1611, doi:10.3762/bjoc.15.164

• , 131.22, 130.18, 128.34, 128.30, 127.42, 126.81, 126.52, 125.30, 125.07. The electrospray ionization mass spectrum of 2 is shown in Figure S3, Supporting Information File 1. HRESIMS (m/z): [M]+ calcd for [C20H14]+, 254.1096, found, 254.1125; [M + Na]+ calcd for [C20H14Na]+, 277.0993; found, 277.1268

• , 127.38, 126.93, 125.52, 122.71. The electrospray ionization mass spectrum of 3 is shown in Figure S6, Supporting Information File 1. HRESIMS (m/z): [M]+ calcd for [C20H13Br]+, 332.0201; found, 332.1679. Synthesis of 4: Compound 4 was prepared by a similar procedure as that used for 2, but with 3 (1.5 g

• spectrum of 4 is shown in Figure S8, Supporting Information File 1. 13C NMR (100 MHz, CDCl3) 154.97, 139.08, 136.98, 136.75, 132.57, 131.31, 130.18, 129.89, 129.66, 128.39, 127.44, 126.97, 126.94, 124.97, 124.94, 120.78, 115.35, 115.27. The electrospray ionization mass spectrum of 4 is shown in Figure S9

Superelectrophilic carbocations: preparation and reactions of a substrate with six ionizable groups

• Sean H. Kennedy,
• Makafui Gasonoo and
• Douglas A. Klumpp

Beilstein J. Org. Chem. 2019, 15, 1515–1520, doi:10.3762/bjoc.15.153

• Sean H. Kennedy Makafui Gasonoo Douglas A. Klumpp Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, IL 60178, USA 10.3762/bjoc.15.153 Abstract A substrate has been prepared having two triarylmethanol centers and four pyridine-type substituent groups. Upon ionization

• benzaldehyde. A nickel-catalyzed procedure gives the dipyridyl intermediate 7 [13]. This is easily oxidized to the diketone 8 and reaction of this substance with 2-lithiopyridine gives the precursor 9. The diol 9 is a substrate with six ionizable groups. Upon ionization in superacidic CF3SO3H (triflic acid

• explained by mechanisms involving highly ionized intermediates. It is proposed that compound 9 initially reacts in excess superacid to give the tetracationic species 12 (Scheme 4). Protonation of the hydroxy groups leads to immediate ionization and formation of the carbocation centers. For related

2,3-Dibutoxynaphthalene-based tetralactam macrocycles for recognizing precious metal chloride complexes

• Li-Li Wang,
• Yi-Kuan Tu,
• Huan Yao and
• Wei Jiang

Beilstein J. Org. Chem. 2019, 15, 1460–1467, doi:10.3762/bjoc.15.146

• isolated with yields of 22% and 19%, respectively. Electrospray ionization (ESI) mass spectra support the isolated products to be the [2 + 2] macrocycles (see Supporting Information File 1). As shown in Figure 1, the 1H NMR spectra are consistent with high-symmetry structures. There are slight differences

Anomeric sugar boronic acid analogues as potential agents for boron neutron capture therapy

• Daniela Imperio,
• Erika Del Grosso,
• Silvia Fallarini,
• Grazia Lombardi and
• Luigi Panza

Beilstein J. Org. Chem. 2019, 15, 1355–1359, doi:10.3762/bjoc.15.135

• about the solution behavior of these compounds we performed MS analysis. The mass spectrum of compound 8 in aqueous solution showed the presence of the cyclic boronic ester both in the positive ionization mode, as adduct at m/z 180 ([M + NH4]+) and m/z 185 ([M + Na]+), and in the negative ionization

Genomics-inspired discovery of massiliachelin, an agrochelin epimer from Massilia sp. NR 4-1

• Jan Diettrich,
• Hirokazu Kage and
• Markus Nett

Beilstein J. Org. Chem. 2019, 15, 1298–1303, doi:10.3762/bjoc.15.128

• Nucleoshell RP18 column (150 × 2.0 mm, Macherey-Nagel) using an Agilent 1260 Infinity LC system combined with a Compact quadrupole-time of flight (Q-TOF) mass spectrometer (Bruker Daltonics). The Q-TOF mass spectrometer was interfaced with an electrospray ionization source. NMR spectra were recorded on a

Bambusuril analogs based on alternating glycoluril and xylylene units

• Tomáš Lízal and
• Vladimír Šindelář

Beilstein J. Org. Chem. 2019, 15, 1268–1274, doi:10.3762/bjoc.15.124

• ESI/APCI as an ion source and a manual pump for sampling. Matrix-assisted laser desorption ionization–time-of-flight mass spectra (MALDI–TOF MS) were measured on a MALDI–TOF MS UltrafleXtreme (Bruker Daltonics) and samples were ionized with the aid of a Nd:YAG laser (355 nm) from α-cyano-4

Self-assembly behaviors of perylene- and naphthalene-crown macrocycle conjugates in aqueous medium

• Xin Shen,
• Bo Li,
• Tiezheng Pan,
• Jianfeng Wu,
• Yangxin Wang,
• Jie Shang,
• Yan Ge,
• Lin Jin and
• Zhenhui Qi

Beilstein J. Org. Chem. 2019, 15, 1203–1209, doi:10.3762/bjoc.15.117

• final compounds were carefully characterized by 1H and 13C NMR spectroscopy and electrospray ionization mass spectroscopy (ESI-MS, Supporting Information File 1, Figures S1–S8). UV–vis absorption and fluorescence spectra of 1 in different solvents, including CHCl3, MeCN, MeOH, H2O, and mixed solvent

Unexpected polymorphism during a catalyzed mechanochemical Knoevenagel condensation

• Sebastian Haferkamp,
• Andrea Paul,
• Adam A. L. Michalchuk and
• Franziska Emmerling

Beilstein J. Org. Chem. 2019, 15, 1141–1148, doi:10.3762/bjoc.15.110

• spectra were recorded with electrospray ionization time of flight mass spectrometry. A Q-TOF Ultima ESI-TOF mass spectrometer (Micromass, Germany) running at 4 kV capillary voltage and a cone voltage of 35 V was used. The collision energy was set to 5 eV. The source temperature was 120 °C whereas the

Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds

• Victoria V. Lipson,
• Tetiana L. Pavlovska,
• Nataliya V. Svetlichnaya,
• Anna A. Poryvai,
• Nikolay Yu. Gorobets,
• Erik V. Van der Eycken,
• Irina S. Konovalova,
• Svetlana V. Shiskina,
• Alexander V. Borisov,
• Vladimir I. Musatov and
• Alexander V. Mazepa

Beilstein J. Org. Chem. 2019, 15, 1032–1045, doi:10.3762/bjoc.15.101

• as internal standard. The mass spectra were recorded on a Varian 1200L GC–MS instrument, ionization by EI at 70 eV. Fast atom bombardment (FAB) mass spectrometry was performed on a VG 70-70EQ mass spectrometer, equipped with an argon primary atom beam, and a m-nitrobenzyl alcohol matrix was used. LC

Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside

• Dimitri Fayolle,
• Nathalie Berthet,
• Bastien Doumeche,
• Olivier Renaudet,
• Peter Strazewski and
• Michele Fiore

Beilstein J. Org. Chem. 2019, 15, 937–946, doi:10.3762/bjoc.15.90

• . Electrospray-ionization mass spectra (ESIMS) were recorded using a Bruker Q-Tof Micromass spectrometer. NMR spectra were recorded in DMSO-d6, CDCl3, CD3OD or DMF-d7 on a Bruker Avance 300 spectrometer at 300 and 75 MHz and on a Bruker Avance 400 at 400 and 100 MHz for 1H, and 13C, respectively. The attached