Ring opening of photogenerated azetidinols as a strategy for the synthesis of aminodioxolanes

• Henning Maag,
• Daniel J. Lemcke and
• Johannes M. Wahl

Beilstein J. Org. Chem. 2024, 20, 1671–1676, doi:10.3762/bjoc.20.148

• demonstrated that the build and release of strain energy can be combined in a simple reaction sequence when appropriately tuning the reaction parameters. Our system relies on a photochemical Norrish–Yang cyclization of α-aminoacetophenones, which provides a sustainable entry to highly strained azetidinols. It

Methyltransferases from RiPP pathways: shaping the landscape of natural product chemistry

• Maria-Paula Schröder,
• Isabel P.-M. Pfeiffer and
• Silja Mordhorst

Beilstein J. Org. Chem. 2024, 20, 1652–1670, doi:10.3762/bjoc.20.147

• peptide methylation. Biocatalysis provides an efficient and sustainable alternative to chemical synthesis strategies. Both NRPS and RiPP biosynthetic machineries can be used for cell-based or in vitro strategies [53]. Especially well suited as biocatalysts are MTs from RiPP pathways, as they demonstrate

New triazinephosphonate dopants for Nafion proton exchange membranes (PEM)

• Fátima C. Teixeira,
• António P. S. Teixeira and
• C. M. Rangel

Beilstein J. Org. Chem. 2024, 20, 1623–1634, doi:10.3762/bjoc.20.145

• , renewable, and environmental-friendly technological processes are being considered using electrochemical devices which convert chemical to electric energy and/or vice versa that, when associated to renewable energy sources, can promote sustainable energy systems [1][2][3][4]. Among them are included proton

• acid groups [22]. These membranes have an excellent chemical stability, but their high proton conduction is dependent of the water content of the membranes which limits their operating temperature range to 80 °C [23]. The importance of the membranes for the new sustainable energy sources fostered the

Benzylic C(sp³)–H fluorination

• Alexander P. Atkins,
• Alice C. Dean and
• Alastair J. J. Lennox

Beilstein J. Org. Chem. 2024, 20, 1527–1547, doi:10.3762/bjoc.20.137

• incorporate fluorine into compounds of interest, with regio and site selectivity pre-determined by the nature of the functionalised carbon. However, the development of C(sp3)–H fluorination methods represents a more sustainable and versatile approach, as there is no requirement to pre-functionalise the

Electrophotochemical metal-catalyzed synthesis of alkylnitriles from simple aliphatic carboxylic acids

• Yukang Wang,
• Yan Yao and
• Niankai Fu

Beilstein J. Org. Chem. 2024, 20, 1497–1503, doi:10.3762/bjoc.20.133

• .20.133 Abstract We report a practical and sustainable electrophotochemical metal-catalyzed protocol for decarboxylative cyanation of simple aliphatic carboxylic acids. This environmentally friendly method features easy availability of substrates, broad functional group compatibility, and directly

Synthesis of 4-functionalized pyrazoles via oxidative thio- or selenocyanation mediated by PhICl₂ and NH₄SCN/KSeCN

• Jialiang Wu,
• Haofeng Shi,
• Xuemin Li,
• Jiaxin He,
• Chen Zhang,
• Fengxia Sun and
• Yunfei Du

Beilstein J. Org. Chem. 2024, 20, 1453–1461, doi:10.3762/bjoc.20.128

• presented a method for the C–H thiocyanation of pyrazoles by using a sustainable catalyst of graphite-phase carbon nitride (g-C3N4) under visible light irradiation (Scheme 1c) [2]. Furthermore, Yao harnessed an electrochemical approach to form the electrophilic SCN+ intermediate, which reacted with

Predicting bond dissociation energies of cyclic hypervalent halogen reagents using DFT calculations and graph attention network model

• Yingbo Shao,
• Zhiyuan Ren,
• Zhihui Han,
• Li Chen,
• Yao Li and
• Xiao-Song Xue

Beilstein J. Org. Chem. 2024, 20, 1444–1452, doi:10.3762/bjoc.20.127

• calculation data. Acknowledgements Thanks to Prof. Dr. Jun Zhang (Shenzhen Bay Laboratory) and Ms. Qiufen Chen (Shenzhen Bay Laboratory & Southern University of Science and Technology) for their help in machine learning as well as Prof. Dr. Xin Li (Nankai University) and Haihe Laboratory of Sustainable

Synthesis of cyclic β-1,6-oligosaccharides from glucosamine monomers by electrochemical polyglycosylation

• Md Azadur Rahman,
• Hirofumi Endo,
• Takashi Yamamoto,
• Shoma Okushiba,
• Norihiko Sasaki and
• Toshiki Nokami

Beilstein J. Org. Chem. 2024, 20, 1421–1427, doi:10.3762/bjoc.20.124

• Md Azadur Rahman Hirofumi Endo Takashi Yamamoto Shoma Okushiba Norihiko Sasaki Toshiki Nokami Department of Chemistry and Biotechnology, Tottori University, 4-101 Koyamacho-minami, Tottori city, 680-8552 Tottori, Japan Center for Research on Green Sustainable Chemistry, Faculty of Engineering

Synthetic applications of the Cannizzaro reaction

• Bhaskar Chatterjee,
• Dhananjoy Mondal and
• Smritilekha Bera

Beilstein J. Org. Chem. 2024, 20, 1376–1395, doi:10.3762/bjoc.20.120

• , solvents, and technologies for the Cannizzaro reaction reflects the broader trend in organic synthesis towards more sustainable and efficient practices. The focus of this review is to highlight some recent advances in synthetic strategies and applications of the Cannizzaro reaction towards the synthesis of

• modern modifications using mild and sustainable reagents, solvents, advanced instrumental techniques, and catalysts in both intramolecular and intermolecular versions of the reaction have made the Cannizzaro reaction an important tool for the synthesis of diverse molecules containing alcohol, acid, ester

Generation of alkyl and acyl radicals by visible-light photoredox catalysis: direct activation of C–O bonds in organic transformations

• Mithu Roy,
• Bitan Sardar,
• Itu Mallick and
• Dipankar Srimani

Beilstein J. Org. Chem. 2024, 20, 1348–1375, doi:10.3762/bjoc.20.119

• photocatalysts, transition-metal photoredox catalysts, and metallaphotocatalysts to produce acyl and alkyl radicals driven by visible light. Keywords: acyl radical; alkyl radical; sustainable catalysis; visible light; Introduction The growing awareness of the necessity for sustainable developments has been

• heightened by the current energy crisis and the adverse impacts of industrialization. The development of green and energy-efficient methods in organic chemistry that use renewable sources of starting materials is considered highly sustainable [1][2][3]. Radical reactions have profound applications in organic

• synthesis [4][5][6][7][8][9]. In the context of sustainable catalysis, visible-light-mediated chemistry is becoming a prominent viable option for radical transformations in the synthesis of biologically useful compounds due to the energy efficiency and environmental friendliness [10][11]. Recently, the

Sustainable tandem acylation/Diels–Alder reaction toward versatile tricyclic epoxyisoindole-7-carboxylic acids in renewable green solvents

• Ayhan Yıldırım

Beilstein J. Org. Chem. 2024, 20, 1308–1319, doi:10.3762/bjoc.20.114

• bisepoxyisoindole-7-carboxylic acids were obtained in good yields after a practical isolation procedure. The results obtained in this study demonstrate the potential of vegetable oils and their renewable materials to provide a reaction medium that is more sustainable than conventional organic solvents in cascade

Synthesis of indano[60]fullerene thioketone and its application in organic solar cells

• Yong-Chang Zhai,
• Shimon Oiwa,
• Shinobu Aoyagi,
• Shohei Ohno,
• Tsubasa Mikie,
• Jun-Zhuo Wang,
• Hirofumi Amada,
• Koki Yamanaka,
• Kazuhira Miwa,
• Naoyuki Imai,
• Takeshi Igarashi,
• Itaru Osaka and
• Yutaka Matsuo

Beilstein J. Org. Chem. 2024, 20, 1270–1277, doi:10.3762/bjoc.20.109

• transporters [9][10]. Organic photovoltaic (OPV) and perovskite solar cell (PSC) technologies have proven to be promising candidates for the sustainable use of solar energy, with power conversion efficiency (PCE) improving to 17% for OPVs and over 25% for PSCs in just a few years [11]. Functionalized fullerene

The Ugi4CR as effective tool to access promising anticancer isatin-based α-acetamide carboxamide oxindole hybrids

• Carolina S. Marques,
• Aday González-Bakker and
• José M. Padrón

Beilstein J. Org. Chem. 2024, 20, 1213–1220, doi:10.3762/bjoc.20.104

• , we highlight the reputation of this reaction approach to access number and scaffold diversity of a library of isatin-based α-acetamide carboxamide oxindole hybrids, promising anticancer agents, in a mild and fast sustainable reaction process. The library was tested against six human solid tumor cell

• aspects. Multicomponent reactions (MCRs) are remarkable tools which demonstrated great potential for more sustainable production of active pharmaceutical ingredients (API’s). These flexible and versatile one-pot transformations in which three or more reagents are combined to access a new complex scaffold

• urgent need to find novel, effective and safe drugs for cancer therapy. Recently, focusing on the design of more potent anticancer drug candidates using more sustainable synthetic processes, we report a new Ugi four-component reaction approach for easy access to Ugi-derived isatin-peptoids in moderate to

Manganese-catalyzed C–C and C–N bond formation with alcohols via borrowing hydrogen or hydrogen auto-transfer

• Mohd Farhan Ansari,
• Atul Kumar Maurya,
• Abhishek Kumar and
• Saravanakumar Elangovan

Beilstein J. Org. Chem. 2024, 20, 1111–1166, doi:10.3762/bjoc.20.98

• reactions allow the sustainable construction of C–C and C–N bonds using alcohols as hydrogen donors. In recent years, manganese complexes have been explored as efficient catalysts in these reactions. This review highlights the significant progress made in manganese-catalyzed C–C and C–N bond-formation

• reactions via hydrogen auto-transfer, emphasizing the importance of this methodology and manganese catalysts in sustainable synthesis strategies. Keywords: alcohols; alkylation; amines; borrowing hydrogen; hydrogen auto-transfer; manganese; Introduction The construction of C–C and C–N bonds is of utmost

• several reviews have been reported on their applications in dehydrogenative coupling reactions [21][22][23][24]. This review focuses mainly on the BH reaction to create sustainable C–C and C–N bonds with manganese catalysts. Review C–N bond formation with alcohols and amines Amines and their derivatives

Light on the sustainable preparation of aryl-cored dibromides

• Fabrizio Roncaglia,
• Alberto Ughetti,
• Nicola Porcelli,
• Biagio Anderlini,
• Andrea Severini and
• Luca Rigamonti

Beilstein J. Org. Chem. 2024, 20, 1076–1087, doi:10.3762/bjoc.20.95

• environment [15]. Nevertheless, in line with the European Union's 'green new deal' guidelines [16], addressing two pivotal issues could facilitate the environmentally conscious utilisation of halogenated compounds as intermediates in chemical processes: The development of more sustainable production methods

Novel route to enhance the thermo-optical performance of bicyclic diene photoswitches for solar thermal batteries

• Akanksha Ashok Sangolkar,
• Rama Krishna Kadiyam and
• Ravinder Pawar

Beilstein J. Org. Chem. 2024, 20, 1053–1068, doi:10.3762/bjoc.20.93

• resource that has potential to meet the increasing energy crises in a sustainable manner [2][3][4]. However, technological devices must be developed that enable a direct capture, conversion, and storage of the solar energy [2][5][6][7]. Molecular solar thermal (MOST) energy storage is one of the most

Carbonylative synthesis and functionalization of indoles

• Alex De Salvo,
• Raffaella Mancuso and
• Xiao-Feng Wu

Beilstein J. Org. Chem. 2024, 20, 973–1000, doi:10.3762/bjoc.20.87

• environmentally friendly. Indeed, the reaction was carried out under 20 bar of CO at 100 °C for 16 h. The indole derivatives were obtained in moderate to good yields and complete conversion of the substrates was observed (Scheme 9). In 1997, Söderberg and co-workers reported a more sustainable procedure. In this

Research progress on the pharmacological activity, biosynthetic pathways, and biosynthesis of crocins

• Zhongwei Hua,
• Nan Liu and
• Xiaohui Yan

Beilstein J. Org. Chem. 2024, 20, 741–752, doi:10.3762/bjoc.20.68

• , novel pharmaceutical systems, such as liposomes, microcapsules, and nanoparticles, were adopted to enhance the stability and bioavailability of these compounds [13][14][15]. To find a sustainable way of supplying crocins, researchers have developed various approaches to produce them, including plant

• heterologous production of crocins in microorganisms to break the current bottleneck of a sustainable supply. It provides the basis for the further development of crocins in the food, cosmetic, and pharmaceutical industries. Review Chemical properties and distribution of crocins More than ten crocins have been

Organic electron transport materials

• Joseph Cameron and
• Peter J. Skabara

Beilstein J. Org. Chem. 2024, 20, 672–674, doi:10.3762/bjoc.20.60

• materials. One of the potential benefits of organic semiconductors is the ability to use solution-processing techniques, which are more sustainable than thermal evaporation which is wasteful and requires high vacuum and temperature. Moreover, organic electron transport layers do not typically need treatment

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

• -Aminopyridine (1a), 4-nitrobenzaldehyde (2a), and tert-butyl isocyanide (3a) were chosen as model substrates and different conditions were screened (Table 1). Glycerol, a green and sustainable solvent, was tried first, but unfortunately, the expected intense orange solid product 4a was obtained in low yields

Recent developments in the engineered biosynthesis of fungal meroterpenoids

• Zhiyang Quan and
• Takayoshi Awakawa

Beilstein J. Org. Chem. 2024, 20, 578–588, doi:10.3762/bjoc.20.50

• Zhiyang Quan Takayoshi Awakawa RIKEN Center for Sustainable Resource Science, Wako, Saitama 351-0198, Japan 10.3762/bjoc.20.50 Abstract Meroterpenoids are hybrid compounds that are partially derived from terpenoids. This group of natural products displays large structural diversity, and many

Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

• Jens Frackenpohl,
• David M. Barber,
• Guido Bojack,
• Birgit Bollenbach-Wahl,
• Ralf Braun,
• Rahel Getachew,
• Sabine Hohmann,
• Kwang-Yoon Ko,
• Karoline Kurowski,
• Bernd Laber,
• Rebecca L. Mattison,
• Thomas Müller,
• Anna M. Reingruber,
• Dirk Schmutzler and
• Andrea Svejda

Beilstein J. Org. Chem. 2024, 20, 540–551, doi:10.3762/bjoc.20.46

• resistant lolium species emphasizes their potential as lead structures to identify tailored solutions for sustainable lolium control in relevant countries (e.g., Australia). In line with good control of other grass weeds (APESV and BROTE, Figure 1), target compound 7b showed the most promising spectrum of

Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles

• Periklis X. Kolagkis,
• Eirini M. Galathri and
• Christoforos G. Kokotos

Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36

• , lowering its LUMO energy, by withdrawing electron-density through a variety of covalent interactions. Green and sustainable approaches Solvent-free processes Alternative processes, that limit environmental pollution and toxic byproducts, came to the forefront of research for the introduction of novel

• [96]. Nanocatalysis Nanocatalysis has emerged over the last decades as a sustainable and green field of organic catalysis that offers unparalleled opportunities for chemical transformations that were previously deemed unfeasible. The use of nanoparticles, compounds with a cross section of less than

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

• years to come to be [7], they are considered limited resources and nonrenewable compared to the current consumption rate [8]. Therefore, a pressing need exists to transition towards renewable energy sources to ensure sustainable energy development and environmental preservation. Solar energy stands out

Cycloaddition reactions of heterocyclic azides with 2-cyanoacetamidines as a new route to C,N-diheteroarylcarbamidines

• Pavel S. Silaichev,
• Tetyana V. Beryozkina,
• Vsevolod V. Melekhin,
• Valeriy O. Filimonov,
• Andrey N. Maslivets,
• Vladimir G. Ilkin,
• Wim Dehaen and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2024, 20, 17–24, doi:10.3762/bjoc.20.3

• ., Yekaterinburg 620002, Russia Innovation Center for Chemical and Pharmaceutical Technologies, Ural Federal University, 19 Mira st., Yekaterinburg 620002, Russia Department of Medical Biology and Genetics, Ural State Medical University, 3 Repina st., Yekaterinburg 620028, Russian Sustainable Chemistry for Metals