A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

• Guido Gambacorta,
• James S. Sharley and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

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

• -resolution mass spectra were obtained using a Thermo Fisher Scientific LTQ Orbitrap XL with an Ion Max API Source. Analyses were made in the positive ionization mode if not otherwise stated. HPLC was performed using a Thermo Scientific Dionex Ultimate 3000 system with diode array detector with a CHIRAL ART

• ), 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

Metal-free nucleophilic trifluoromethylselenolation via an iodide-mediated umpolung reactivity of trifluoromethylselenotoluenesulfonate

• Kevin Grollier,
• Alexis Taponard,
• Arnaud De Zordo-Banliat,
• Emmanuel Magnier and
• Thierry Billard

Beilstein J. Org. Chem. 2020, 16, 3032–3037, doi:10.3762/bjoc.16.252

• partitioned between Et2O or pentane and water. The aqueous layer was extracted with Et2O and pentane and the combined organic layers were dried over MgSO4, filtered and concentrated to dryness. The crude residue was purified by chromatography to afford the desired products 3, 4, or 5. State of the art

A proposed sustainability index for synthesis plans based on input provenance and output fate: application to academic and industrial synthesis plans for vanillin as a case study

• John Andraos

Beilstein J. Org. Chem. 2020, 16, 2346–2362, doi:10.3762/bjoc.16.196

• “provenance” borrowed from the authentication of objects of art as genuine by art dealers and museum curators during the selling and purchasing of them at auctions. The provenance of an object of art potentially links it to its true creator. Obtaining provenance constitutes amassing traceable hard evidence

• that links the original artist and his or her work via the chain of its ownership through time from its creation to the present day. Provenances are necessary to establish the authenticity of a piece of art and thus distinguish it from a forgery. The concept of provenance or tracing has also been

GlypNirO: An automated workflow for quantitative N- and O-linked glycoproteomic data analysis

• Toan K. Phung,
• Cassandra L. Pegg and
• Benjamin L. Schulz

Beilstein J. Org. Chem. 2020, 16, 2127–2135, doi:10.3762/bjoc.16.180

• diseased states [8]. The current state-of-the art technology for the characterisation, identification, and quantification of the glycome or glycoproteome is liquid chromatography coupled to tandem mass spectrometry (LC–MS/MS) [9]. Popular and powerful glycoproteomic workflows typically involve standard

Three new O-isocrotonyl-3-hydroxybutyric acid congeners produced by a sea anemone-derived marine bacterium of the genus Vibrio

• Dandan Li,
• Enjuro Harunari,
• Tao Zhou,
• Naoya Oku and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1869–1874, doi:10.3762/bjoc.16.154

• and NMR analyses combined with state-of-the-art chemical approaches should unveil the detailed structure of PHAs and possibly offer a clue to alter the property of these promising biomaterials. Experimental General experimental procedures Optical rotations were recorded on a JASCO P-1030 polarimeter

Tuneable access to indole, indolone, and cinnoline derivatives from a common 1,4-diketone Michael acceptor

• Dalel El-Marrouki,
• Sabrina Touchet,
• Abderrahmen Abdelli,
• Hédi M’Rabet,
• Mohamed Lotfi Efrit and
• Philippe C. Gros

Beilstein J. Org. Chem. 2020, 16, 1722–1731, doi:10.3762/bjoc.16.144

• ][45][46][47]. Moreover, arylhydrazones and arylhydrazines/hydrazines can be used as well, respectively, as partners in [4 + 2] cyclization reactions [48][49][50][51] or by reacting mostly with carbonyl derivatives [52][53][54][55]. From the state-of-the-art, a strategy that promotes the synthesis of

NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides

• Alyn T. Davies,
• Mark D. Greenhalgh,
• Alexandra M. Z. Slawin and
• Andrew D. Smith

Beilstein J. Org. Chem. 2020, 16, 1572–1578, doi:10.3762/bjoc.16.129

• proceed via enamine intermediates (Figure 1B) [14][15][16][17][18][19]. The state of the art within this area has been recently demonstrated by Dixon and co-workers, who showed that bifunctional BIMP catalysts could promote the enantioselective addition of typically recalcitrant aryl ketones to

Heterogeneous photocatalysis in flow chemical reactors

• Christopher G. Thomson,
• Ai-Lan Lee and
• Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

• has shifted the paradigms of photochemistry, opening new avenues of research with safer and scalable processes that can be readily implemented in academia and industry. Current state-of-the-art photocatalysts are homogeneous transition metal complexes that have favourable photophysical properties

Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis

• Stephanie G. E. Amos,
• Marion Garreau,
• Luca Buzzetti and
• Jerome Waser

Beilstein J. Org. Chem. 2020, 16, 1163–1187, doi:10.3762/bjoc.16.103

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

• Nuray Altinolcek Ahmet Battal Mustafa Tavasli William J. Peveler Holly A. Yu Peter J. Skabara Department of Chemistry, Faculty of Science-Art, Uludag University, 16059 Nilufer, Bursa, Turkey Department of Elementary School Education, Faculty of Education, Mus Alparslan University, 49100, Mus

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

• spectrophotometer V-570, and fluorescence spectra were measured with a JASCO PL spectrofluorometer FP-6600. Fluorescence quantum yields were measured on a HAMAMATSU Absolute PL Quantum Yield Measurement System C9920-02G. TLC and gravity column chromatography were performed on Art. 5554 (Merck KGaA) plates and

Synthesis and circularly polarized luminescence properties of BINOL-derived bisbenzofuro[2,3-b:3’,2’-e]pyridines (BBZFPys)

• Ryo Takishima,
• Yuji Nishii,
• Tomoaki Hinoue,
• Yoshitane Imai and
• Masahiro Miura

Beilstein J. Org. Chem. 2020, 16, 325–336, doi:10.3762/bjoc.16.32

• with JASCO FP-8500 spectrometer. Quantum yield was determined using an integration sphere system. CD and CPL spectra were recorded with JASCO J-820AC and JASCO CPL-300 spectrometers. HPLC analysis was carried out with JASCO EXTREMA (PU4180/MD4015/CO4065) equipped with YMC CHIRAL ART Amylose-SA and YMC

• CHIRAL ART Cellulose-SB columns. Preparation of 6,6'-di-tert-butyl-BINOL (1) Compound 1 was prepared according to a literature procedure [55]. 1H NMR (400 MHz, CDCl3) δ 1.38 (s, 18H), 4.96 (s, 2H), 7.13 (d, J = 8.9 Hz, 2H), 7.36 (d, J = 8.9 Hz, 2H), 7.41 (dd, J = 2.0, 8.9 Hz, 2H), 7.82 (d, J = 2.0 Hz, 2H

• ), 7.94 (d, J = 8.9 Hz, 2H); 13C NMR (100 MHz, CDCl3) δ 31.25, 34.61, 110.62, 117.54, 123.49, 124.01, 126.36, 129.35, 131.34, 131.42, 146.69, 152.29; HRMS–APCI (m/z): [M + H]+ calcd for C28H31O2, 399.2330; found, 399.2319. The enantiomeric purity was confirmed by HPLC analysis: CHIRAL ART Amylose-SA

A combinatorial approach to improving the performance of azoarene photoswitches

• Joaquin Calbo,
• Aditya R. Thawani,
• Rosina S. L. Gibson,
• Andrew J. P. White and
• Matthew J. Fuchter

Beilstein J. Org. Chem. 2019, 15, 2753–2764, doi:10.3762/bjoc.15.266

• ring, so-called arylazopyrazoles, which have excellent potential against the current state of the art (Figure 1b) [17][18]. Specifically, arylazopyrazole 4pzMe can be near quantitatively (>98%) photoswitched in both directions, and 4pzH demonstrated an exceptionally long thermal Z-isomer half-life

• two high performance designs of state-of-the-art azo photoswitches – N-methylated pyrazole plus an o-substituted benzene – would be advantageous for further improving the properties of the azopyrazoles (Figure 1c). It is important to note that Jan Ravoo and co-workers [23] have reported a bis-ortho

A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

• Munmun Ghosh,
• Valmik S. Shinde and
• Magnus Rueping

Beilstein J. Org. Chem. 2019, 15, 2710–2746, doi:10.3762/bjoc.15.264

• -stage functionalizations. Although this field has been periodically reviewed over the last few decades, a single article addressing all attempts to date will be useful for organic chemists working in this field and for those who would like to obtain an overview of the current state of the art of

Perspective isomorphs – a new classification of molecular structures based on artistic and chemical concepts

• Jannis Neumann,
• Ansgar Schnurr and
• Hermann A. Wegner

Beilstein J. Org. Chem. 2019, 15, 2319–2326, doi:10.3762/bjoc.15.224

• a quintessential part in research as well as for scientific communication in general. A special challenge is the visualization of the invisible, such as atoms and molecules. Visualizations are also deeply rooted in the discipline of art offering in the respect untapped potential in cross

• -fertilization with natural sciences. Here we show a new classification of molecular structures, so-called perspective isomorphs, applying an interdisciplinary crossing of epistemological concepts between chemistry and art. The idea is based on the notion that molecules can be classified, if they appear

• isomorphs and its discussions herein will extend current models and stimulate the discourse about the nature of atoms and molecules and especially their models. Keywords: art and science; nomenclature; perspective; representation in chemistry; structure; Introduction Up to now, epistemological concepts of

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

• Gagandeep Kour Reen,
• Ashok Kumar and
• Pratibha Sharma

Beilstein J. Org. Chem. 2019, 15, 1612–1704, doi:10.3762/bjoc.15.165

• to 2015 [34][35][36][37][38][39]. This review covers a substantial time period of the literature, from the year 2006 to August 2018 (except for the reports mentioned under previously reported reviews), with state-of-the-art methodologies, and reflecting some of the changing approaches and challenges

Electrophilic oligodeoxynucleotide synthesis using dM-Dmoc for amino protection

• Shahien Shahsavari,
• Dhananjani N. A. M. Eriyagama,
• Bhaskar Halami,
• Vagarshak Begoyan,
• Marina Tanasova,
• Jinsen Chen and
• Shiyue Fang

Beilstein J. Org. Chem. 2019, 15, 1116–1128, doi:10.3762/bjoc.15.108

• that contain electrophilic groups. However, at the current state of art one drawback of the technology is that large excess aniline has to be used as a scavenger to prevent the deprotection side product 1 from reacting with the deprotected ODNs via Michael addition. Aniline is a weak nucleophile, but

Design, synthesis and spectroscopic properties of crown ether-capped dibenzotetraaza[14]annulenes

• Krzysztof M. Zwoliński and
• Julita Eilmes

Beilstein J. Org. Chem. 2019, 15, 617–622, doi:10.3762/bjoc.15.57

• Creation of polycyclic architectures predisposed to perform higher forms of molecular behaviour is essential for advancing the art of biomimetic chemistry. Therefore, the first crown ether-capped DBTAAs, featuring a face-to-face arrangement of the macrocyclic components, have been synthesized in

Synthesis of a tyrosinase inhibitor by consecutive ethenolysis and cross-metathesis of crude cashew nutshell liquid

• Jacqueline Pollini,
• Valentina Bragoni and
• Lukas J. Gooßen

Beilstein J. Org. Chem. 2018, 14, 2737–2744, doi:10.3762/bjoc.14.252

• , 122.8, 115.9, 110.4, 36.5, 32.0, 31.9, 29.8, 29.69, 29.68, 29.65, 29.6, 29.5, 29.4, 29.3, 22.7, 22.2, 14.1 ppm. The analytical data matched those reported in the literature [40]. State-of-the-art metathesis catalysts. Targeted conversion of CNSL into a tyrosinase inhibitor. Previous synthesis of 2

Pathoblockers or antivirulence drugs as a new option for the treatment of bacterial infections

• Matthew B. Calvert,
• Varsha R. Jumde and
• Alexander Titz

Beilstein J. Org. Chem. 2018, 14, 2607–2617, doi:10.3762/bjoc.14.239

• stability [21]. Such biphenyl mannoside-derived compounds are the current state of the art and are being further developed by the company Fimbrion (St Louis, MO) in collaboration with GlaxoSmithKline. In many cases, lectins have more than one carbohydrate binding site or are clustered in proximity

• ]. Therefore, it is likely that combinations of drugs will be applied for drug-resistant bacterial infections, as is currently the state of the art for many viral infections. Mannosides as inhibitors of the lectin FimH from uropathogenic Escherichia coli. Galactosides targeting uropathogenic Escherichia coli

Evaluation of dispersion type metal···π arene interaction in arylbismuth compounds – an experimental and theoretical study

• Ana-Maria Preda,
• Małgorzata Krasowska,
• Lydia Wrobel,
• Philipp Kitschke,
• Phil C. Andrews,
• Jonathan G. MacLellan,
• Lutz Mertens,
• Marcus Korb,
• Tobias Rüffer,
• Heinrich Lang,
• Alexander A. Auer and
• Michael Mehring

Beilstein J. Org. Chem. 2018, 14, 2125–2145, doi:10.3762/bjoc.14.187

• compounds of the type Ar3Bi (Ar = C4H3NMe, C4H3O, C4H3S, C4H3Se) [28][29]. Other state of the art examples on the formation of supramolecular assemblies via dispersion type metal···π arene intermolecular interactions [10][11] were summarized by Caracelli et al., and recently Tiekink classified this type of

Functionalization of graphene: does the organic chemistry matter?

• Artur Kasprzak,
• Agnieszka Zuchowska and
• Magdalena Poplawska

Beilstein J. Org. Chem. 2018, 14, 2018–2026, doi:10.3762/bjoc.14.177

• , reaction mechanisms, and state of the art of organic chemistry. Point-by-point recommendations are also given for the proper application of organic chemistry principles in covalent functionalization of graphene-family materials. The chemistry of the reactive groups of graphene-family materials covers many

Biocatalytic synthesis of the Green Note trans-2-hexenal in a continuous-flow microreactor

• Morten M. C. H. van Schie,
• Tiago Pedroso de Almeida,
• Gabriele Laudadio,
• Florian Tieves,
• Elena Fernández-Fueyo,
• Timothy Noël,
• Isabel W. C. E. Arends and
• Frank Hollmann

Beilstein J. Org. Chem. 2018, 14, 697–703, doi:10.3762/bjoc.14.58

• beverages. One attractive access to trans-2-hex-2-enal is the oxidation of the corresponding allylic alcohol to the aldehyde. Though at first sight an oxidation of primary alcohols to the corresponding aldehydes does not appear to be a major challenge, the methods of the state-of-the-art are mostly plagued

Heterogeneous Pd catalysts as emulsifiers in Pickering emulsions for integrated multistep synthesis in flow chemistry

• Katharina Hiebler,
• Georg J. Lichtenegger,
• Manuel C. Maier,
• Eun Sung Park,
• Renie Gonzales-Groom,
• Bernard P. Binks and
• Heidrun Gruber-Woelfler

Beilstein J. Org. Chem. 2018, 14, 648–658, doi:10.3762/bjoc.14.52

• analysed using different state-of-the-art methods. Details of the characterisation were published recently [37]. Here, only the most important characteristics are summarised. The obtained X-ray diffraction (XRD) profiles proved the nanocrystallinity of the catalyst particles, which either show single phase