Ortho-ester-substituted diaryliodonium salts enabled regioselective arylocyclization of naphthols toward 3,4-benzocoumarins

• Ke Jiang,
• Cheng Pan,
• Limin Wang,
• Hao-Yang Wang and
• Jianwei Han

Beilstein J. Org. Chem. 2024, 20, 841–851, doi:10.3762/bjoc.20.76

• , CAS for helpful discussion and instrumental analysis. Funding The work was supported by the Industry-University-Research Collaborative Innovation Fund for Chinese Universities-DeZhou Project (2021DZ030) and the Natural Science Foundation of Shanghai (20ZR1413500); Shanghai Municipal Science and

HPW-Catalyzed environmentally benign approach to imidazo[1,2-a]pyridines

• Luan A. Martinho and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2024, 20, 628–637, doi:10.3762/bjoc.20.55

• existing ones. Keywords: GBB-3CR; imidazo[1,2-a]pyridine; microwave; phosphotungstic acid; Introduction Imidazo[1,2-a]pyridine is a privileged structure that plays an important role in organic synthesis and in the pharmaceutical industry. This scaffold is present in drugs with several biological

A new analog of dihydroxybenzoic acid from Saccharopolyspora sp. KR21-0001

• Rattiya Janthanom,
• Yuta Kikuchi,
• Hiroki Kanto,
• Tomoyasu Hirose,
• Arisu Tahara,
• Takahiro Ishii,
• Arinthip Thamchaipenet and
• Yuki Inahashi

Beilstein J. Org. Chem. 2024, 20, 497–503, doi:10.3762/bjoc.20.44

• actinomycetes, which are believed to be rich sources of interestingly new compounds. Bioactive compounds are vastly beneficial in medicine, pharmaceutical industry, and agriculture [7][8]. The thoughtful exploration of novel sources for acquiring new compounds is crucial, and the strategies employed in this

• and biotechnological innovations. Continued research in this area has the potential to uncover valuable compounds that contribute to human health, pharmaceutical industry, and environmental sustainability. Experimental Taxonomic analysis Saccharopolyspora sp. KR21-0001 was isolated from soil in Ōha

Nucleophilic functionalization of thianthrenium salts under basic conditions

• Xinting Fan,
• Duo Zhang,
• Xiangchuan Xiu,
• Bin Xu,
• Yu Yuan,
• Feng Chen and
• Pan Gao

Beilstein J. Org. Chem. 2024, 20, 257–263, doi:10.3762/bjoc.20.26

• accessible and have significant importance in the pharmaceutical industry, positioning them as appealing candidates for C(sp3) coupling due to their availability as a common chemical feedstock. However, due to the high bond dissociation energy of the C–O bond and the poor leaving ability of the hydroxy group

Substitution reactions in the acenaphthene analog of quino[7,8-h]quinoline and an unusual synthesis of the corresponding acenaphthylenes by tele-elimination

• Ekaterina V. Kolupaeva,
• Narek A. Dzhangiryan,
• Alexander F. Pozharskii,
• Oleg P. Demidov and
• Valery A. Ozeryanskii

Beilstein J. Org. Chem. 2024, 20, 243–253, doi:10.3762/bjoc.20.24

• and used in medicine, food industry, catalysts, dyes, functional materials, oil refining, and electronics [1][2]. Quinoline and its derivatives have antibiotic, antimalarial, antitumor, anti-inflammatory, antihypertensive, and antiretroviral properties [3][4]. Therefore, at present, there is a need

Photochromic derivatives of indigo: historical overview of development, challenges and applications

• Gökhan Kaplan,
• Zeynel Seferoğlu and
• Daria V. Berdnikova

Beilstein J. Org. Chem. 2024, 20, 228–242, doi:10.3762/bjoc.20.23

• Despite thousands of years of use, the demand for indigo derivatives in the industry is still growing. The main reason for this is the unusual photostability and color fastness of indigo as industrial dye. This exceptional photostability of indigo and its derivatives has attracted significant scientific

Optimizing reaction conditions for the light-driven hydrogen evolution in a loop photoreactor

• Pengcheng Li,
• Daniel Kowalczyk,
• Johannes Liessem,
• Mohamed M. Elnagar,
• Dariusz Mitoraj,
• Radim Beranek and
• Dirk Ziegenbalg

Beilstein J. Org. Chem. 2024, 20, 74–91, doi:10.3762/bjoc.20.9

• around an internal concentrically fitted draft tube, and are widely used in industry, such as microbiology fermentation and Fischer–Tropsch synthesis [21][22]. This type of reactors provides very high mass transfer rates, well-defined fluid flow patterns, and a simple design [23][24]. The construction

Identification of the p-coumaric acid biosynthetic gene cluster in Kutzneria albida: insights into the diazotization-dependent deamination pathway

• Seiji Kawai,
• Akito Yamada,
• Yohei Katsuyama and
• Yasuo Ohnishi

Beilstein J. Org. Chem. 2024, 20, 1–11, doi:10.3762/bjoc.20.1

• Inc. (Shiga, Japan). Primers were purchased from Thermo Fisher Scientific (Waltham, MA, USA). Chemicals for the enzymatic assay were purchased from Sigma-Aldrich (St. Louis, MO, USA). Chemicals for organic synthesis were purchased from Tokyo Chemical Industry (Tokyo, Japan). 3-Aminocoumaric acid (3

Controlling the reactivity of La@C₈₂ by reduction: reaction of the La@C₈₂ anion with alkyl halide with high regioselectivity

• Yutaka Maeda,
• Saeka Akita,
• Mitsuaki Suzuki,
• Michio Yamada,
• Takeshi Akasaka,
• Kaoru Kobayashi and
• Shigeru Nagase

Beilstein J. Org. Chem. 2023, 19, 1858–1866, doi:10.3762/bjoc.19.138

• otherwise stated. ODCB was distilled over P2O5 under vacuum prior to use. HPLC was performed on an LC-9201 instrument (Japan Analytical Industry Co., Ltd.) by monitoring the UV absorption at 330 nm with toluene as the eluent. Mass spectrometry was performed using a Bruker AUTOFLEX III smart beam with

GlAIcomics: a deep neural network classifier for spectroscopy-augmented mass spectrometric glycans data

• Thomas Barillot,
• Baptiste Schindler,
• Baptiste Moge,
• Elisa Fadda,
• Franck Lépine and
• Isabelle Compagnon

Beilstein J. Org. Chem. 2023, 19, 1825–1831, doi:10.3762/bjoc.19.134

• dedicated analytical tools (glycomics) is clearly identified as a critical bottleneck, impeding the full development of glycosciences despite their relevance for various strategic fields such as pharmaceutical and food industry; bio-based materials and renewable energy, and their considerable potential

A novel recyclable organocatalyst for the gram-scale enantioselective synthesis of (S)-baclofen

• Gyula Dargó,
• Dóra Erdélyi,
• Balázs Molnár,
• Péter Kisszékelyi,
• Zsófia Garádi and
• József Kupai

Beilstein J. Org. Chem. 2023, 19, 1811–1824, doi:10.3762/bjoc.19.133

• , acetonitrile, with 91–100% efficiency, and the catalyst was reused in five reaction cycles without the loss of activity and selectivity. Keywords: baclofen; catalyst recovery; lipophilic cinchona squaramide; organocatalysis; stereoselective catalysis; Introduction In today’s chemical industry, catalytic

• organocatalysts has been a major breakthrough in the realization of enantioselective transformations. Stereoselective synthesis is essential in the pharmaceutical industry, as the development of drugs often requires the production of enantiomerically pure chiral compounds [6][7][8]. The application of

• investigated a new, industry-relevant synthesis route of baclofen in the gram-scale. The chiral precursor 17 of baclofen was obtained with quantitative yield and excellent enantiomeric excess (up to 96%). The catalyst was applied in five consecutive runs without a decrease in catalytic activity, moreover, the

Radical chemistry in polymer science: an overview and recent advances

• Zixiao Wang,
• Feichen Cui,
• Yang Sui and
• Jiajun Yan

Beilstein J. Org. Chem. 2023, 19, 1580–1603, doi:10.3762/bjoc.19.116

• Zixiao Wang Feichen Cui Yang Sui Jiajun Yan School of Physical Science and Technology, ShanghaiTech University, 393 Middle Huaxia Rd., Shanghai, 201210, China 10.3762/bjoc.19.116 Abstract Radical chemistry is one of the most important methods used in modern polymer science and industry. Over the

• materials. Radical depolymerization, an efficient approach to destroy polymers, finds applications in two distinct fields, semiconductor industry and environmental protection. Polymer chemistry has largely diverged from organic chemistry with the fine division of modern science but polymer chemists

• . Polymers produced by radical polymerization represent a major fraction of all industrial polymers. 1.1 Radical polymerization in nature In addition to well-established processes in modern industry, examples of radical polymerization exist in nature. The principle of the two cases in the following text is

Cyclodextrins permeabilize DPPC liposome membranes: a focus on cholesterol content, cyclodextrin type, and concentration

• Ghenwa Nasr,
• Hélène Greige-Gerges,
• Sophie Fourmentin,
• Abdelhamid Elaissari and
• Nathalie Khreich

Beilstein J. Org. Chem. 2023, 19, 1570–1579, doi:10.3762/bjoc.19.115

• industry: a review” by N. Morini-Crini; S. Fourmentin; É. Fenyvesi; E. Lichtfouse; G. Torri; M. Fourmentin; G. Crini, Environmental Chemistry Letters, Vol. 19, pp 2581–2617, 2021), Copyright 2021 Springer Nature. Journal home page: https://www.springer.com/journal/10311. This content is not subject to CC

Synthesis of 5-arylidenerhodanines in L-proline-based deep eutectic solvent

• Stéphanie Hesse

Beilstein J. Org. Chem. 2023, 19, 1537–1544, doi:10.3762/bjoc.19.110

• , volatile solvents, hard conditions, and/or difficult purifications. However, green chemistry has become a crucial sub-discipline in the field of chemistry and the chemical industry is giving major priority to sustainable processes. Since a few years, deep eutectic solvents (DES) are considered as a

Cyanothioacetamides as a synthetic platform for the synthesis of aminopyrazole derivatives

• Valeriy O. Filimonov,
• Alexandra I. Topchiy,
• Vladimir G. Ilkin,
• Tetyana V. Beryozkina and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2023, 19, 1191–1197, doi:10.3762/bjoc.19.87

• exhibit a variety of biological activity. Their application is known in pharmacy [1][2][3][4] and agro-industry [5][6][7][8]. Especially such compounds are used to protect plants from insects and weeds (Figure 1). Thus, pinoxaden is a commercially available inhibitor of acetyl-CoA carboxylase and affects

Selective and scalable oxygenation of heteroatoms using the elements of nature: air, water, and light

• Damiano Diprima,
• Hannes Gemoets,
• Stefano Bonciolini and
• Koen Van Aken

Beilstein J. Org. Chem. 2023, 19, 1146–1154, doi:10.3762/bjoc.19.82

• byproducts, and increased efficiency in industrial processes. As such, this field of research is of great importance and interest to both academia and industry. This work showcases a sustainable and catalyst-free oxidation method for heteroatoms (e.g., S, P, and Se) using only air, water and light. An

• flow using the HANU flow reactor, indicating scalability and improving safety. Keywords: catalyst-free; flow chemistry; oxygen; photochemistry; sustainable oxidation; Introduction Oxidation reactions are widely used in the chemical industry, but are often problematic due to challenges with

• of heteroatoms, making them a promising alternative to traditional oxidants in the chemical industry [9]. Our interest in sustainable oxidation methodologies led us to study the selective oxidation of various heteroatoms to their corresponding oxides, including sulfides to sulfoxides, phosphine to

Photoredox catalysis harvesting multiple photon or electrochemical energies

• Mattia Lepori,
• Simon Schmid and
• Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

• context of deeply reductive reactions, dissolving alkali metal conditions have remained the most commonly employed both in academia and industry for over a century and even to date continue to be used despite their hazards, poor selectivity and chemical waste [7][8][9][10]. Nowadays, excellent alternative

• appropriate in certain contexts of application. Broadly speaking, it can be concluded that carrying out reactions with conPET, both in academia and industry, has a lower barrier of accessibility due to more intuitive/standardized reactor setups. Essentially, the reactor setup can be identical to standard

Five new sesquiterpenoids from agarwood of Aquilaria sinensis

• Hong Zhou,
• Xu-Yang Li,
• Hong-Bin Fang,
• He-Zhong Jiang and
• Yong-Xian Cheng

Beilstein J. Org. Chem. 2023, 19, 998–1007, doi:10.3762/bjoc.19.75

• , Tokyo, Japan). Plant material The resinous wood of Aquilaria sinensis was purchased from Hainan Xiangshu Agarwood Industry Groud Co., Ltd., July 2018. The material was identified by the Gansu Institute for Drug Control, and a voucher specimen (CHYX0642) was deposited at School of Pharmaceutical Sciences

Pyridine C(sp²)–H bond functionalization under transition-metal and rare earth metal catalysis

• Haritha Sindhe,
• Malladi Mounika Reddy,
• Karthikeyan Rajkumar,
• Akshay Kamble,
• Amardeep Singh,
• Anand Kumar and
• Satyasheel Sharma

Beilstein J. Org. Chem. 2023, 19, 820–863, doi:10.3762/bjoc.19.62

Palladium-catalyzed enantioselective three-component synthesis of α-arylglycine derivatives from glyoxylic acid, sulfonamides and aryltrifluoroborates

• Bastian Jakob,
• Nico Schneider,
• Luca Gengenbach and
• Georg Manolikakes

Beilstein J. Org. Chem. 2023, 19, 719–726, doi:10.3762/bjoc.19.52

• products. Keywords: amino acids; asymmetric catalysis; multicomponent reaction; palladium catalysis; Petasis reaction; sulfonamides; Introduction α-Amino acids play a crucial role in every aspect of our human life [1]. They are important synthetic intermediates in the chemical industry and used for the

Strategies in the synthesis of dibenzo[b,f]heteropines

• David I. H. Maier,
• Barend C. B. Bezuidenhoudt and
• Charlene Marais

Beilstein J. Org. Chem. 2023, 19, 700–718, doi:10.3762/bjoc.19.51

• David I. H. Maier Barend C. B. Bezuidenhoudt Charlene Marais Department of Chemistry, University of the Free State, PO Box 339, Bloemfontein, 9300, South Africa 10.3762/bjoc.19.51 Abstract The dibenzo[b,f]azepine skeleton is important in the pharmaceutical industry, not only in terms of existing

Photocatalytic sequential C–H functionalization expediting acetoxymalonylation of imidazo heterocycles

• Deepak Singh,
• Shyamal Pramanik and
• Soumitra Maity

Beilstein J. Org. Chem. 2023, 19, 666–673, doi:10.3762/bjoc.19.48

• from academia and industry. Herein, we report a direct C-3 acetoxymalonylation of imidazo heterocycles using relay C–H functionalization enabled by organophotocatalysis starring zinc acetate in the triple role of an activator, ion scavenger as well as an acetylating reagent. The mechanistic

C3-Alkylation of furfural derivatives by continuous flow homogeneous catalysis

• Grédy Kiala Kinkutu,
• Catherine Louis,
• Myriam Roy,
• Juliette Blanchard and
• Julie Oble

Beilstein J. Org. Chem. 2023, 19, 582–592, doi:10.3762/bjoc.19.43

• of the development of a sustainable chemical industry [1][2][3][4]. Furfurals, which are versatile platform molecules derived from renewable lignocellulose present in agricultural wastes [5][6][7][8], have proven to be of great importance for the preparation of value-added chemicals, biofuels, as

• temperature). Thus, despite the synthetic interest of the molecules that can be obtained, transfers to industry are difficult. In order to circumvent this drawback, we considered transposing these batch reactions to a flow chemistry process. In recent years, the use of continuous flow chemistry in organic

A new oxidatively stable ligand for the chiral functionalization of amino acids in Ni(II)–Schiff base complexes

• Alena V. Dmitrieva,
• Oleg A. Levitskiy,
• Yuri K. Grishin and
• Tatiana V. Magdesieva

Beilstein J. Org. Chem. 2023, 19, 566–574, doi:10.3762/bjoc.19.41

• testing; Introduction Asymmetric synthesis of functionalized amino acids is a subject of intense research because these compounds are of great demand for pharmaceutical industry, health care, and food production [1][2][3]. Various approaches to enantiomerically enriched amino acids have been developed

Total synthesis: an enabling science

• Bastien Nay

Beilstein J. Org. Chem. 2023, 19, 474–476, doi:10.3762/bjoc.19.36

• (biomimetic synthesis) [14]. In addition, total syntheses have also been achieved with enzymes, strengthening the links to biology [15]. Total synthesis is not limited to academic laboratories but rather also pursued in industry, where a particular efficiency and economy of tasks is of paramount importance