One-pot synthesis of epoxides from benzyl alcohols and aldehydes

• Edwin Alfonzo,
• Jesse W. L. Mendoza and
• Aaron B. Beeler

Beilstein J. Org. Chem. 2018, 14, 2308–2312, doi:10.3762/bjoc.14.205

• characterization for all new compounds described herein. Acknowledgements Financial support from Boston University and National Science Foundation (ABB CHE-1555300) is gratefully acknowledged. We thank Dr. Norman Lee (Boston University) for high-resolution mass spectrometry data. NMR (CHE-0619339) and MS

Hypervalent iodine compounds for anti-Markovnikov-type iodo-oxyimidation of vinylarenes

• Igor B. Krylov,
• Stanislav A. Paveliev,
• Mikhail A. Syroeshkin,
• Alexander A. Korlyukov,
• Pavel V. Dorovatovskii,
• Yan V. Zubavichus,
• Gennady I. Nikishin and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2018, 14, 2146–2155, doi:10.3762/bjoc.14.188

• higher (25% on average) than that of N-hydroxysuccinimide (2b). Structures of the iodo-oxyimides 3aa–ka, 3ab–db, 3fb, 3hb and 3kb were confirmed by 1D and 2D NMR spectroscopy, IR spectroscopy, high-resolution mass spectrometry and elemental analysis. An additional confirmation of the structure of 3ca was

A self-assembled photoresponsive gel consisting of chiral nanofibers

• Lei Zou,
• Dan Han,
• Zhiyi Yuan,
• Dongdong Chang and
• Xiang Ma

Beilstein J. Org. Chem. 2018, 14, 1994–2001, doi:10.3762/bjoc.14.174

• beginning, which can be detected by high-resolution mass spectrometry (Figure S7, Supporting Information File 1). Then, the dimers and single molecules 3 were able to assemble together through π–π stacking and hydrogen bonding to fabricate the nanofibers. Finally, those fibers twisted with each other to

Water-soluble SNS cationic palladium(II) complexes and their Suzuki–Miyaura cross-coupling reactions in aqueous medium

• Alphonse Fiebor,
• Richard Tia,
• Banothile C. E. Makhubela and
• Henok H. Kinfe

Beilstein J. Org. Chem. 2018, 14, 1859–1870, doi:10.3762/bjoc.14.160

• AgOTf to provide the desired SNS-Pd(II) complex 17a in quantitative yield (Scheme 1). The structure of the complex was established using NMR spectroscopy and high-resolution mass spectrometry. Among others, the downfield shift of all the protons in the complex, when compared to the corresponding protons

Preparation and X-ray structure of 2-iodoxybenzenesulfonic acid (IBS) – a powerful hypervalent iodine(V) oxidant

• Irina A. Mironova,
• Pavel S. Postnikov,
• Rosa Y. Yusubova,
• Akira Yoshimura,
• Thomas Wirth,
• Viktor V. Zhdankin,
• Victor N. Nemykin and
• Mekhman S. Yusubov

Beilstein J. Org. Chem. 2018, 14, 1854–1858, doi:10.3762/bjoc.14.159

• problems, IBS was previously characterized by 1H and 13C NMR, IR spectroscopy, high-resolution mass spectrometry, and elemental analysis. However, all previously reported attempts to grow single crystals of IBS from methanol or acetonitrile resulted in reduction with the formation of 2

Synthesis and photophysical studies of a multivalent photoreactive Ru^II-calix[4]arene complex bearing RGD-containing cyclopentapeptides

• Sofia Kajouj,
• Lionel Marcelis,
• Alice Mattiuzzi,
• Adrien Grassin,
• Damien Dufour,
• Pierre Van Antwerpen,
• Didier Boturyn,
• Eric Defrancq,
• Mathieu Surin,
• Julien De Winter,
• Pascal Gerbaux,
• Ivan Jabin and
• Cécile Moucheron

Beilstein J. Org. Chem. 2018, 14, 1758–1768, doi:10.3762/bjoc.14.150

• the ArH, ArCH2 and OPr group are differentiated. Moreover, complex 7 was also characterized by high-resolution mass spectrometry (HRMS). The ESI mass spectrum displays two intense signals at m/z 764.736 and m/z 1642.456 that are attributed respectively to the doubly charged 72+ and singly charged [7

Hypervalent iodine-guided electrophilic substitution: para-selective substitution across aryl iodonium compounds with benzyl groups

• Cyrus Mowdawalla,
• Faiz Ahmed,
• Tian Li,
• Kiet Pham,
• Loma Dave,
• Grace Kim and
• I. F. Dempsey Hyatt

Beilstein J. Org. Chem. 2018, 14, 1039–1045, doi:10.3762/bjoc.14.91

• . Acknowledgements This research was supported by Faculty Development Grants and a Frederick Bettelheim Research Award from Adelphi University to I. F. Dempsey Hyatt. We are grateful to Dr. Brian Stockman for his NMR expertise and Dr. Daniel A. Todd for acquisition of the high resolution mass spectrometry data at

An uracil-linked hydroxyflavone probe for the recognition of ATP

• Márton Bojtár,
• Péter Zoltán Janzsó-Berend,
• Dávid Mester,
• Dóra Hessz,
• Mihály Kállay,
• Miklós Kubinyi and
• István Bitter

Beilstein J. Org. Chem. 2018, 14, 747–755, doi:10.3762/bjoc.14.63

• alkaline hydrogen peroxide to obtain the clickable fluorophore. All new compounds were characterized by NMR and high-resolution mass spectrometry. Optical spectroscopy The solubility of the UHF probe was very poor in water which resulted in the decrease of fluorescence over time upon dilution from the

AuBr₃-catalyzed azidation of per-O-acetylated and per-O-benzoylated sugars

• Jayashree Rajput,
• Srinivas Hotha and
• Madhuri Vangala

Beilstein J. Org. Chem. 2018, 14, 682–687, doi:10.3762/bjoc.14.56

• and 100 MHz spectrometer, respectively using CDCl3 as the solvent. Chemical shifts (δ) are given in ppm. For perbenzoate compounds 10–15, tetramethyl silane was used as internal standard. Electrospray ionization (ESI) was used for high resolution mass spectrometry (HRMS). An FTIR spectrometer was used

Synthesis and stability of strongly acidic benzamide derivatives

• Frederik Diness,
• Niels J. Bjerrum and
• Mikael Begtrup

Beilstein J. Org. Chem. 2018, 14, 523–530, doi:10.3762/bjoc.14.38

• Bruker 500 MHz spectrometer at 298 K with methanol-d4, DMSO-d6 or hexafluorobenzene as internal standard. High-resolution mass spectrometry (HRMS) was performed on a Bruker MALDI–TOF spectrometer. General procedure Benzoyl chloride (10.0 mmol) in Et2O (10 mL) was added dropwise to a solution of

Synthesis of 1,3-cis-disubstituted sterically encumbered imidazolidinone organocatalysts

• Jan Wallbaum and
• Daniel B. Werz

Beilstein J. Org. Chem. 2017, 13, 2577–2583, doi:10.3762/bjoc.13.254

• were made by combination of H,H-COSY, HSQC, HMBC and NOESY experiments. In some cases signals in the 13C NMR spectrum are missing because of bad relaxation of the respective signals. ESI high-resolution mass spectrometry was carried out on a FTICR instrument. IR spectra were measured on an ATR

A concise flow synthesis of indole-3-carboxylic ester and its derivatisation to an auxin mimic

• Marcus Baumann,
• Ian R. Baxendale and
• Fabien Deplante

Beilstein J. Org. Chem. 2017, 13, 2549–2560, doi:10.3762/bjoc.13.251

• % of tallest signal). Low and high-resolution mass spectrometry was performed using the indicated techniques on instruments equipped with Acquity UPLC and a lock-mass electrospray ion source. For accurate mass measurements the deviation from the calculated formula is reported in ppm. Melting points

The chemistry and biology of mycolactones

• Matthias Gehringer and
• Karl-Heinz Altmann

Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159

• activity. Further purification of this material by reversed-phase HPLC and subsequent characterization by high-resolution mass spectrometry and two-dimensional NMR spectroscopy unveiled a 12-membered macrolactone substituted with two polyketide-derived side chains (Figure 1). Based on its mycobacterial

• Leadlay and co-workers applying LC−sequential and high-resolution mass spectrometry in combination with deuterium exchange experiments [54]. Instead of the additional hydroxy group proposed by the Small group, these studies provided strong evidence for mycolactone D (3) to feature an extra methyl group at

• originally been proposed by the Small group (11, Figure 3) after partial TLC purification and subsequent high-resolution mass spectrometry and 1H NMR spectroscopy (although no NMR data are shown in their report) [50]. Shortly afterwards, the Leadlay group proposed structure 6 (Figure 2) based on tandem mass

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

• , respectively, as zero ppm. All chemical shifts (δ) are reported in ppm, and coupling constants (J) are given in hertz (Hz). High-resolution mass spectrometry (HRMS) analyses were performed on a Waters Xevo G2 Q-TOF mass spectrometer equipped with an ESI source operating in the positive ion mode. The accurate

A speedy route to sterically encumbered, benzene-fused derivatives of privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline

• Olga Bakulina,
• Alexander Ivanov,
• Vitalii Suslonov,
• Dmitry Dar’in and
• Mikhail Krasavin

Beilstein J. Org. Chem. 2017, 13, 1413–1424, doi:10.3762/bjoc.13.138

• reaction with homophthalic anhydride (HPA). The compounds obtained contain a benzene-fused, privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline core and are distinctly encumbered from steric perspective. The novel compounds have been characterized by NMR spectroscopy, high-resolution mass

• spectrometry and X-ray crystallography and certain regularities in the NMR behavior have been established, leading a set of rules for stereochemical assignment based on the NMR data. A Mannich-type adduct between HPA and an imine (previously only postulated as a crucial intermediate en route to CCR products

Unpredictable cycloisomerization of 1,11-dien-6-ynes by a common cobalt catalyst

• Abdusalom A. Suleymanov,
• Dmitry V. Vasilyev,
• Valentin V. Novikov,
• Yulia V. Nelyubina and
• Dmitry S. Perekalin

Beilstein J. Org. Chem. 2017, 13, 639–643, doi:10.3762/bjoc.13.62

• structure to that of 1a,b. We can speculate that COOEt groups of 1l formed a chelate complex with ZnI2 and therefore strongly diminished its Lewis acidity, which is necessary for catalyst activation. All the compounds obtained were characterized by 1H and 13C NMR spectroscopy as well as high-resolution mass

• -spectrometry (for ethers, which are oils) or elemental analysis (for tosylamides, which are crystalline solids). The structures of the starting dienyne 1h and the cyclohexene trans-2b were established by X-ray crystallography. The structures of cis-2b and 3b had been reported previously [11][43]. Conclusion To

Structure–efficiency relationships of cyclodextrin scavengers in the hydrolytic degradation of organophosphorus compounds

• Sophie Letort,
• Michaël Bosco,
• Benedetta Cornelio,
• Frédérique Brégier,
• Sébastien Daulon,
• Géraldine Gouhier and
• François Estour

Beilstein J. Org. Chem. 2017, 13, 417–427, doi:10.3762/bjoc.13.45

• imidazole reduced the accessibility of substrates 11 and 12 to position 3. Thus, compounds 13 and 14 were isolated in comparable yields of 37% and 27%, respectively and this time without significantly different reactivities observed for the precursors 9 and 10. High resolution mass spectrometry (ESI+ HRMS

Decarboxylative and dehydrative coupling of dienoic acids and pentadienyl alcohols to form 1,3,6,8-tetraenes

• Ghina’a I. Abu Deiab,
• Mohammed H. Al-Huniti,
• I. F. Dempsey Hyatt,
• Emma E. Nagy,
• Kristen E. Gettys,
• Sommayah S. Sayed,
• Christine M. Joliat,
• Paige E. Daniel,
• Rupa M. Vummalaneni,
• Andrew T. Morehead Jr,
• Andrew L. Sargent and
• Mitchell P. Croatt

Beilstein J. Org. Chem. 2017, 13, 384–392, doi:10.3762/bjoc.13.41

• North Carolina Biotechnology Center (BRG-1205) and University of North Carolina at Greensboro is gratefully acknowledged. The authors thank Dr. Franklin J. Moy for assisting with analysis of NMR data and Dr. Daniel A. Todd for acquisition of the high resolution mass spectrometry data at the Triad Mass

Characterization of the synthetic cannabinoid MDMB-CHMCZCA

• Carina Weber,
• Stefan Pusch,
• Dieter Schollmeyer,
• Sascha Münster-Müller,
• Michael Pütz and
• Till Opatz

Beilstein J. Org. Chem. 2016, 12, 2808–2815, doi:10.3762/bjoc.12.279

• : 2.1 mm, particle size: 2.7 μm; Supelco) was used at a temperature of 40 °C. The capillary voltage was set to 3500 V and the capillary exit voltage was set according to the respective target mass. High-resolution mass spectrometry High-resolution ESI mass spectrometry was performed on a Waters QTof

Amidofluorene-appended lower rim 1,3-diconjugate of calix[4]arene: synthesis, characterization and highly selective sensor for Cu²⁺

• Rahman Hosseinzadeh,
• Mohammad Nemati,
• Reza Zadmard and
• Maryam Mohadjerani

Beilstein J. Org. Chem. 2016, 12, 1749–1757, doi:10.3762/bjoc.12.163

• -dicyclohexylcarbodiimide (DCC) in dichloromethane at room temperature gave the desired receptor L in 81% yield (Scheme 2). All the compounds including receptor L has been characterized by various spectral techniques such as 1H, 13C NMR and high resolution mass spectrometry (HRMS) (see Supporting Information File 1

Natural products from microbes associated with insects

• Christine Beemelmanns,
• Huijuan Guo,
• Maja Rischer and
• Michael Poulsen

Beilstein J. Org. Chem. 2016, 12, 314–327, doi:10.3762/bjoc.12.34

• the brood cell with the protective symbiont, beewolf females ensure that the larvae take up the symbionts from the surrounding soil while spinning the cocoon. Using high resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR) spectroscopy, the protective secondary metabolites were

N-Methylphthalimide-substituted benzimidazolium salts and PEPPSI Pd–NHC complexes: synthesis, characterization and catalytic activity in carbon–carbon bond-forming reactions

• Senem Akkoç,
• Yetkin Gök,
• İlhan Özer İlhan and
• Veysel Kayser

Beilstein J. Org. Chem. 2016, 12, 81–88, doi:10.3762/bjoc.12.9

• for the ν(CN) bond of 1–4, respectively. Compounds 2 and 4 among these salts were further characterized by using high-resolution mass spectrometry (HRMS). The mass spectra demonstrated m/z peaks at 382.16 and 391.18 for the cationic moieties against the calculated value of m/z 382.43 and 391.44 for 2

Easy access to heterobimetallic complexes for medical imaging applications via microwave-enhanced cycloaddition

• Nicolas Desbois,
• Sandrine Pacquelet,
• Adrien Dubois,
• Clément Michelin and
• Claude P. Gros

Beilstein J. Org. Chem. 2015, 11, 2202–2208, doi:10.3762/bjoc.11.239

• (e.g., pH fix at 7 for Cu2+ and pH fix at 3 for Ga3+). The isolated copper and gallium NOTA derivatives 12a,b were characterized by high-resolution mass spectrometry. Scope of the cycloaddition reaction Over the past decade, click chemistry has been applied to the synthesis of a wide variety of

Conformational equilibrium in supramolecular chemistry: Dibutyltriuret case

• Karina Mroczyńska,
• Małgorzata Kaczorowska,
• Erkki Kolehmainen,
• Ireneusz Grubecki,
• Marek Pietrzak and
• Borys Ośmiałowski

Beilstein J. Org. Chem. 2015, 11, 2105–2116, doi:10.3762/bjoc.11.227

• resolution mass spectrometry (HRMS) for the study of the association processes of 1 with benzoate 5 and naphthyridine 10 anions and to examine self-association of 1. The ESI–HRMS was previously successfully used for the study of complexation of triuret derivative with cations [44] and has been demonstrated

• complex. For detailed discussion that supports experimental findings refer to the computations section in Supporting Information File 1. Mass spectrometry To have a more complete view of properties of 1 we applied the combination of soft ionization technique electrospray ionization (ESI) with high

Tetrathiafulvalene-based azine ligands for anion and metal cation coordination

• Awatef Ayadi,
• Aziz El Alamy,
• Olivier Alévêque,
• Magali Allain,
• Nabil Zouari,
• Mohammed Bouachrine and
• Abdelkrim El-Ghayoury

Beilstein J. Org. Chem. 2015, 11, 1379–1391, doi:10.3762/bjoc.11.149

• desired ligands L1 and L2 in 75% and 63% isolated yields, respectively. The structures of the new ligands were characterized by 1H and 13C NMR, UV–visible and IR spectroscopy, high resolution mass spectrometry and elemental analysis. Crystal structure description Details about data collection and