Icilio Guareschi and his amazing “1897 reaction”

• Gian Cesare Tron,
• Alberto Minassi,
• Giovanni Sorba,
• Mara Fausone and
• Giovanni Appendino

Beilstein J. Org. Chem. 2021, 17, 1335–1351, doi:10.3762/bjoc.17.93

• the answer given by Röntgen when he was asked why he had not patented X-rays (“They were invented by Nature, not by me.”) [24]. Rather than a moral virtue, this lack of connection with industry is nowadays identified by historians as a major impediment to a robust development of science in Italy

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

• temperatures, fragrance ingredients/intermediates make ideal candidates for continuous-flow manufacturing. This review highlights the potential crossover between a multibillion dollar industry and the flourishing sub-field of flow chemistry evolving within the discipline of organic synthesis. This is

• illustrated through selected examples of industrially important transformations specific to the fragrances and flavours industry and by highlighting the advantages of conducting these transformations by using a flow approach. This review is designed to be a compendium of techniques and apparatus already

• industry In 2018, the flavours and fragrances (F&F) market was valued $26.5 billion with an annual growth of 4.8%, this industry represents a strong economic market expected to be worth more than $38.5 billion by 2026 in the rapidly expanding global market [1]. In general, there is an approximate equal

Recent advances in palladium-catalysed asymmetric 1,4–additions of arylboronic acids to conjugated enones and chromones

• Jan Bartáček,
• Jan Svoboda,
• Martin Kocúrik,
• Jaroslav Pochobradský,
• Alexander Čegan,
• Miloš Sedlák and
• Jiří Váňa

Beilstein J. Org. Chem. 2021, 17, 1048–1085, doi:10.3762/bjoc.17.84

• , continuous-flow reactions are currently a general challenge, especially for the pharmaceutical industry. The prerequisite for a successful continuous synthesis in the field of asymmetric addition reactions to enones is the mastery of recyclable heterogeneous catalysis. Very recently, we reported [57] the

Beyond ribose and phosphate: Selected nucleic acid modifications for structure–function investigations and therapeutic applications

• Christopher Liczner,
• Kieran Duke,
• Gabrielle Juneau,
• Martin Egli and
• Christopher J. Wilds

Beilstein J. Org. Chem. 2021, 17, 908–931, doi:10.3762/bjoc.17.76

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

• Shivani Gulati,
• Stephy Elza John and
• Nagula Shankaraiah

Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71

• provided an easy access to the synthesis of complex bioactive molecules with multiple point diversity incorporating up to eight components in one-pot [8]. The pharmaceutical industry has witnessed a considerable surge in drug synthesis via multicomponent strategies [9][10][11], including the synthesis of

• and selective heating of the heterogeneous catalyst [20][21][22][23]. Even though the MWA technology is advantageous, a major challenge posed is the scale-up at the industry level where protocol efficiency at kilogram scale is mandatory. With rapid heat generation, and litres of solvents often safety

Synthetic reactions driven by electron-donor–acceptor (EDA) complexes

• Zhonglie Yang,
• Yutong Liu,
• Kun Cao,
• Xiaobin Zhang,
• Hezhong Jiang and
• Jiahong Li

Beilstein J. Org. Chem. 2021, 17, 771–799, doi:10.3762/bjoc.17.67

• over the last five years. Cyclization reactions In the pharmaceutical industry, retail drugs with a heterocyclic composition have exceeded 60% of the market volume. Hence, cyclization reaction innovation seems to be a requisite for pharmaceutical industry and human health. As an outstanding way, free

Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of N-tosyl-1,2,3-triazoles

• Soumyaranjan Pati,
• Renata G. Almeida,
• Eufrânio N. da Silva Júnior and
• Irishi N. N. Namboothiri

Beilstein J. Org. Chem. 2021, 17, 762–770, doi:10.3762/bjoc.17.66

• class of heterocycles presents important biological properties, such as antiviral, anti-inflammatory, antimicrobial etc. and are considered as key building blocks in pharmaceutical industry [6][7][8][9]. Thus, they marked their presence as prominent scaffolds in many drug molecules such as tazobactam

Valorisation of plastic waste via metal-catalysed depolymerisation

• Francesca Liguori,
• Carmen Moreno-Marrodán and
• Pierluigi Barbaro

Beilstein J. Org. Chem. 2021, 17, 589–621, doi:10.3762/bjoc.17.53

• into soil [14][15], oceans [16][17], crustaceans [18] and rain [19]. Valorisation of plastic waste, via chemical conversion into reusable building blocks, may contribute to solving these problems while representing a strategy to reduce the carbon footprint of the chemical industry [20][21]. The

• decomposition of the polymeric chain, monomers or oligomers, depending on the waste polymer and the process. The as-obtained compounds can be reused as raw materials for the process industry (hence the term feedstock) to produce chemicals, fuels or other polymers. Thermochemical processes include pyrolysis [55

• plastics. Heterogeneous systems are preferred by industry due to the easier separation from the reaction mixture, reuse and integration into existing reactor equipment [106][107]. Metal-based catalysts have been used for both solvolytic and hydrogenolytic methods, wherein the latter are usually achieved by

Amino- and polyaminophthalazin-1(2H)-ones: synthesis, coordination properties, and biological activity

• Zbigniew Malinowski,
• Emilia Fornal,
• Agata Sumara,
• Renata Kontek,
• Karol Bukowski,
• Beata Pasternak,
• Dariusz Sroczyński,
• Joachim Kusz,
• Magdalena Małecka and
• Monika Nowak

Beilstein J. Org. Chem. 2021, 17, 558–568, doi:10.3762/bjoc.17.50

• need to develop new and improve the existing methods for the synthesis of aminophthalazinones is important from the point of view of their properties and pharmaceutical industry interest. In the present work, we report results of our research on the synthesis, application as ligands in complexes, and

Synthesis of trifluoromethyl ketones by nucleophilic trifluoromethylation of esters under a fluoroform/KHMDS/triglyme system

• Yamato Fujihira,
• Yumeng Liang,
• Makoto Ono,
• Kazuki Hirano,
• Takumi Kagawa and
• Norio Shibata

Beilstein J. Org. Chem. 2021, 17, 431–438, doi:10.3762/bjoc.17.39

• , and methyl esters are readily available inexpensive precursors. Besides, glymes are versatile solvents for chemical processes in industry [74] would the protocol be useful for the industrial extension, although there are still many points to be overcome such as requirements of low temperature, two

Coupling biocatalysis with high-energy flow reactions for the synthesis of carbamates and β-amino acid derivatives

• Alexander Leslie,
• Thomas S. Moody,
• Megan Smyth,
• Scott Wharry and
• Marcus Baumann

Beilstein J. Org. Chem. 2021, 17, 379–384, doi:10.3762/bjoc.17.33

• flow chemistry is by now a mature field with chemists in both academia and industry regularly reporting on the multitude of benefits arising from exploiting reactor miniaturization [1][2][3][4][5]. The steady increase of applications highlighting improved syntheses is thereby paralleled by a growing

• . Batch hydrolysis of the ester group in the presence of the carbamate. Supporting Information Supporting Information File 4: Experimental details and spectroscopic data. Funding We gratefully acknowledge support from Science Foundation Ireland through the SFI Industry Fellowship Program for the project

Supramolecular polymers with reversed viscosity/temperature profile for application in motor oils

• Jan-Erik Ostwaldt,
• Christoph Hirschhäuser,
• Stefan K. Maier,
• Carsten Schmuck and
• Jochen Niemeyer

Beilstein J. Org. Chem. 2021, 17, 105–114, doi:10.3762/bjoc.17.11

• depicted in the background of the graphical abstract was reproduced from https://thenounproject.com/korawan_m/collection/industry-oil-gas-power-outline/?i=909361 (“motor oil” by BomSymbols, from the Noun Project, distributed under the terms of the Creative Commons Attribution 3.0 United States, https

Synthesis of tetrafluorinated piperidines from nitrones via a visible-light-promoted annelation reaction

• Vyacheslav I. Supranovich,
• Igor A. Dmitriev and
• Alexander D. Dilman

Beilstein J. Org. Chem. 2020, 16, 3104–3108, doi:10.3762/bjoc.16.260

• heterocyclic compounds play an important role in pharmaceutical industry and related areas [1][2]. Among the variety of aromatic and saturated structures, the piperidine ring has a special role, as it is the most widely occurring form of nitrogen in FDA-approved drugs [3]. The ability of fluorine atoms to

All-carbon [3 + 2] cycloaddition in natural product synthesis

• Zhuo Wang and
• Junyang Liu

Beilstein J. Org. Chem. 2020, 16, 3015–3031, doi:10.3762/bjoc.16.251

• that the all-carbon [3 + 2] cycloaddition will gain further attention from the synthetic community, including scientists from academia and pharmaceutical industry, for methodic innovation and the efficient synthesis of biologically important natural products. Highly-substituted five-membered carbocycle

Regioselective synthesis of heterocyclic N-sulfonyl amidines from heteroaromatic thioamides and sulfonyl azides

• Vladimir Ilkin,
• Vera Berseneva,
• Tetyana Beryozkina,
• Tatiana Glukhareva,
• Lidia Dianova,
• Wim Dehaen,
• Eugenia Seliverstova and
• Vasiliy Bakulev

Beilstein J. Org. Chem. 2020, 16, 2937–2947, doi:10.3762/bjoc.16.243

• , rich chemistry and technically useful properties of heterocyclic compounds have made them a focal point of science and industry over the years. Heterocyclic compounds including azoles and azines have been found in natural products, and they are included in the structures of nucleic acids, vitamins

A novel and robust heterogeneous Cu catalyst using modified lignosulfonate as support for the synthesis of nitrogen-containing heterocycles

• Bingbing Lai,
• Meng Ye,
• Ping Liu,
• Minghao Li,
• Rongxian Bai and
• Yanlong Gu

Beilstein J. Org. Chem. 2020, 16, 2888–2902, doi:10.3762/bjoc.16.238

• to the fast deactivation of catalysts, which consequently impair the recyclability of the catalysts [8][9][10][11]. Therefore, special efforts should be paid to enhancing the robustness of heterogeneous metal catalysts. Sodium lignosulphonate (LS) is a waste from the paper-making industry, containing

One-pot multicomponent green Hantzsch synthesis of 1,2-dihydropyridine derivatives with antiproliferative activity

• Giovanna Bosica,
• Kaylie Demanuele,
• José M. Padrón and
• Adrián Puerta

Beilstein J. Org. Chem. 2020, 16, 2862–2869, doi:10.3762/bjoc.16.235

• the pharmaceutical industry [3][8]. An analysis of the market shows that there are over 7000 drugs derived from dihydropyridines, some of which are blockbuster drugs, such as Tamiflu®, dioscorine, ibogaine, and isoquinuclidines [9][10]. Classically the Hantzsch synthesis involved the condensation of 2

Dirhamnolipid ester – formation of reverse wormlike micelles in a binary (primerless) system

• David Liese,
• Hans Henning Wenk,
• Xin Lu,
• Jochen Kleinen and
• Gebhard Haberhauer

Beilstein J. Org. Chem. 2020, 16, 2820–2830, doi:10.3762/bjoc.16.232

• described by Leisinger et al. [9]. Rhamnolipids possess some advantages, that make them interesting candidates as cleaning agents or additives for care applications in the consumer goods industry. They can be produced in a fermentation process from renewable nontropic material [10][11]. RL are also

Dawn of a new era in industrial photochemistry: the scale-up of micro- and mesostructured photoreactors

• Emine Kayahan,
• Mathias Jacobs,
• Leen Braeken,
• Leen C.J. Thomassen,
• Simon Kuhn,
• Tom van Gerven and
• M. Enis Leblebici

Beilstein J. Org. Chem. 2020, 16, 2484–2504, doi:10.3762/bjoc.16.202

• Leuven, Leuven, Belgium 10.3762/bjoc.16.202 Abstract Photochemical activation routes are gaining the attention of the scientific community since they can offer an alternative to the traditional chemical industry that mainly utilizes thermochemical activation of molecules. Photoreactions are fast and

• : microreactor; microreactor scale-up; monolith reactors; packed bed reactor; photoreactor scale-up; Review Introduction In the traditional chemical industry, thermochemical activation routes are mostly preferred. Light can also activate some molecules, which leads to fast and selective reaction pathways

• sequestration [7]. Still, photochemistry has not been exploited much in industry since the distribution of light inside a photoreactor brings a lot of complexity to the reactor design. Unlike thermochemical reactions, it is not feasible to scale up photoreactions by increasing the dimensions of the reactor due

Conformational preferences of fluorine-containing agrochemicals and their implications for lipophilicity prediction

• Daniela Rodrigues Silva,
• Joyce K. Daré and
• Matheus P. Freitas

Beilstein J. Org. Chem. 2020, 16, 2469–2476, doi:10.3762/bjoc.16.200

• lipophilicity with the molecular conformation. Keywords: dipole moment; fluorinated compounds; gauche effect; herbicides; log P; Introduction Whilst in the last years the agrochemical industry has encountered a period of downturn affected by new regulations, low crop prices, biochemical resistance, among

• other variables, recent events have shown signs of recovery [1]. Currently, the agrochemical industry focuses on introducing new efficient and more environmentally friendly products, that attend the new regulation requirements, for replacing those agrochemicals that were banned due to either their

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

• fossil-fuel derived and renewable sources. Dutch and Belgian chemical engineers proposed an extended thermodynamic analysis considering exergy and lost work to address the sustainability potential of the chemical process industry [2][3][4]. Horvath and co-workers put forth the following sustainability

• assumptions and guesswork since there are no proper centralized data kept for tracking end-of-life waste of any product manufactured in the chemical industry. Hence, for the purposes of calculating SI, estimating is the weakest link. Having described the three mass fractions related to the provenance of

• , unitless), skin dose (SD, mg), and flash point (FP, degrees K). Table 1 shows a revised and expanded formatted listing of normalized OSI values for various solvents used in the chemical industry. In our past work [20] describing a presentation of a “standardized process green synthesis report” for chemical

Photosensitized direct C–H fluorination and trifluoromethylation in organic synthesis

• Shahboz Yakubov and
• Joshua P. Barham

Beilstein J. Org. Chem. 2020, 16, 2151–2192, doi:10.3762/bjoc.16.183

• , light is inexpensive, nontoxic, noncontaminating, ample (or “limitless” in the case of sunlight) and a renewable source of energy for environmentally-friendly and “green” chemical synthesis. As a consequence of comprehending the detrimental impact of human industry on the environment, new methods to

Synthesis of monophosphorylated lipid A precursors using 2-naphthylmethyl ether as a protecting group

• Jundi Xue,
• Ziyi Han,
• Gen Li,
• Khalisha A. Emmanuel,
• Cynthia L. McManus,
• Qiang Sui,
• Dongmian Ge,
• Qi Gao and
• Li Cai

Beilstein J. Org. Chem. 2020, 16, 1955–1962, doi:10.3762/bjoc.16.162

• Jundi Xue Ziyi Han Gen Li Khalisha A. Emmanuel Cynthia L. McManus Qiang Sui Dongmian Ge Qi Gao Li Cai Shanghai University of Engineering Science, 333 Long Teng Road, Shanghai 201620, China China State Institute of Pharmaceutical Industry, 285 Gebaini Rd, Shanghai 201203, China Department of

Pauson–Khand reaction of fluorinated compounds

• Jorge Escorihuela,
• Daniel M. Sedgwick,
• Alberto Llobat,
• Mercedes Medio-Simón,
• Pablo Barrio and
• Santos Fustero

Beilstein J. Org. Chem. 2020, 16, 1662–1682, doi:10.3762/bjoc.16.138

• signal). In addition, the use of fluorinated organic compounds in other key industrial fields is also of paramount importance. The agrochemical and materials industries, together with the aforementioned pharmaceutical industry, are perhaps the fields where organofluorinated compounds have exerted the

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