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

• carbonylation reactions, represent a simple and more environmentally friendly method for the synthesis of important organic compounds. Since the development of the Wacker process, the study of oxidative carbonylations has made enormous progress by investigating even the possibility of catalyzing carbonylative

• 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

• regioselectivity of the process. The regioselectivity was good with a regioisomeric ratio of 95:5. All reactions took place in the presence of Pd(OAc)2 as catalyst, cataCXium as ligand, and K2CO3 as base. Besides, the authors proposed glyoxylic acid monohydrate as an environmentally friendly CO surrogate (Scheme

Innovative synthesis of drug-like molecules using tetrazole as core building blocks

• Jingyao Li,
• Ajay L. Chandgude,
• Qiang Zheng and
• Alexander Dömling

Beilstein J. Org. Chem. 2024, 20, 950–958, doi:10.3762/bjoc.20.85

• envisioned the use of multicomponent reactions in both steps. The use of MCRs provides the benefits of simplicity, speed, complexity, and diversity with the minimum number of steps and with an environmentally friendly nature. First, we focused on the use of the Passerini-tetrazole reaction for the synthesis

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

• and environmentally friendly adsorbents for the selective adsorption of crocins from an aqueous solution of saffron pollen [25]. Pharmacological activity of crocins Various pharmacological studies have shown that crocins are effective against diseases of the central nervous system (neurodegenerative

Chemoenzymatic synthesis of macrocyclic peptides and polyketides via thioesterase-catalyzed macrocyclization

• Senze Qiao,
• Zhongyu Cheng and
• Fuzhuo Li

Beilstein J. Org. Chem. 2024, 20, 721–733, doi:10.3762/bjoc.20.66

• presents a significant opportunity to establish more efficient and environmentally friendly approaches toward bioactive macrocyclic peptides and macrolides [23]. Nevertheless, the native substrates of TE domains are tethered with PCP or ACP in biosynthetic pathways, which have to be simplified to

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

• protocol showed a lower E-factor by far, which makes it a cleaner and environmentally friendly process. Through the mass intensity parameter, our procedure also showed a lower mass loss compared to the total raw material used to produce a given mass of product. The calculations of these parameters can be

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

• reaction between aldehydes with indoles, while focusing on the more environmentally friendly methods developed over the years. Keywords: aldehyde; BIMs; Friedel–Crafts reaction; green chemistry; indole; Review Medicinal properties In recent years, diindolylmethane (DIM, 1) and its derivatives known as

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

• ]. As an alternative to the chemical synthesis of indigo, environmentally friendly biological approaches towards constructing the indigo scaffold are also being developed for nearly a century [5][6][7][8]. The biosynthetic methods include production of indigo by microorganisms and enzymatic synthesis

Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions

• Karolis Leitonas,
• Brigita Vigante,
• Dmytro Volyniuk,
• Audrius Bucinskas,
• Pavels Dimitrijevs,
• Sindija Lapcinska,
• Pavel Arsenyan and
• Juozas Vidas Grazulevicius

Beilstein J. Org. Chem. 2023, 19, 1867–1880, doi:10.3762/bjoc.19.139

• pyridine-3,5-dicarbonitrile moiety attracted a great deal of attention in the last decade in the field of materials chemistry, precisely in the development of novel heavy-metal-free pure organic light-emitting diodes (OLEDs). Inexpensive and environmentally friendly emitters are vital for organic

• . Further investigations and optimizations of the properties of such compounds may lead to the realization of environmentally friendly and cost-effective OLED technologies. Experimental Synthesis Unless otherwise stated, all reagents were purchased from commercial suppliers and used without further

Quinoxaline derivatives as attractive electron-transporting materials

• Zeeshan Abid,
• Liaqat Ali,
• Sughra Gulzar,
• Faiza Wahad,
• Raja Shahid Ashraf and
• Christian B. Nielsen

Beilstein J. Org. Chem. 2023, 19, 1694–1712, doi:10.3762/bjoc.19.124

• materials. In addition, Qx-based materials offer notable sustainability advantages. These materials possess low environmental impact and can be synthesized from abundant precursors, making them both cost-effective and environmentally friendly compared to certain inorganic semiconductor materials. Moreover

A series of perylene diimide cathode interlayer materials for green solvent processing in conventional organic photovoltaics

• Kathryn M. Wolfe,
• Shahidul Alam,
• Eva German,
• Fahad N. Alduayji,
• Maryam Alqurashi,
• Frédéric Laquai and
• Gregory C. Welch

Beilstein J. Org. Chem. 2023, 19, 1620–1629, doi:10.3762/bjoc.19.119

• deviation. All of the devices are comparable to the PFN-Br CIL, which is the one that is employed the most for PM6:Y6 OPVs. PFN-Br is most often processed from methanol [32], which is a solvent that is not well suited for the production of large-area or environmentally friendly devices owing to a high vapor

• with any traditional transport layer and are applicable for a wide range of high-efficiency OPVs. Furthermore, the CILs processed from ethyl acetate can be applied to fabricating fully environmentally friendly OPVs based on eco-friendly or green solvents, especially for indoor applications. a) Select

Lewis acid-promoted direct synthesis of isoxazole derivatives

• Dengxu Qiu,
• Chenhui Jiang,
• Pan Gao and
• Yu Yuan

Beilstein J. Org. Chem. 2023, 19, 1562–1567, doi:10.3762/bjoc.19.113

• environmentally friendly catalysts, our laboratory recently developed an alternative approach to the synthesis of isooxazoles starting from 2-methylquinoline and alkynes mediated by Brønsted acids in good yields (Scheme 1, reaction 3) [20]. The utilization of main element metal aluminum salts in organic synthesis

N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

• Fatemeh Doraghi,
• Seyedeh Pegah Aledavoud,
• Mehdi Ghanbarlou,
• Bagher Larijani and
• Mohammad Mahdavi

Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106

• stereogenic carbon centers bearing a sulfur atom. Although, significant efforts have been made to form enantioselective C–S bonds, the direct sulfenylation with more green, economical, and environmentally friendly sulfenylating reagents remains a challenge for organic chemists. N-(Sulfenyl)succinimides

Non-noble metal-catalyzed cross-dehydrogenation coupling (CDC) involving ether α-C(sp³)–H to construct C–C bonds

• Hui Yu and
• Feng Xu

Beilstein J. Org. Chem. 2023, 19, 1259–1288, doi:10.3762/bjoc.19.94

• Negishi reaction (Zn) [1], Stille reaction (Sn) [2], Kumada reaction (Mg) [3], and Suzuki reaction (Pd) [4] (Scheme 1a). However, these coupling reactions involve a metal exchange step that generates a considerable amount of reaction waste, such as metal salts, which are not environmentally friendly. To

•  27) [88]. This route provides an environmentally friendly and practical approach to alkyl-substituted alkynes. Co-catalyzed reactions In recent years, cobalt has exhibited great application potential as a cross-dehydrogenation coupling catalyst due to its low price, environmentally friendliness, and

• application of this method still limited by sustainability, safety, and cost factors. Therefore, further development to shorten the reaction time, improve the reaction efficiency, and reduce energy consumption in an environmentally friendly, practical, and safe method for CDC will be a continuous process [131

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

• , 9800 Deinze, Belgium 10.3762/bjoc.19.82 Abstract Sustainable oxidation protocols aim to provide an environmentally friendly and cost-effective method for the production of various chemicals and materials. The development of such protocols can lead to reduced energy consumption, fewer harmful

Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach

• Dileep Kumar Singh and
• Rajesh Kumar

Beilstein J. Org. Chem. 2023, 19, 928–955, doi:10.3762/bjoc.19.71

• well-known method for synthesizing a large number of N-substituted pyrroles. In recent years, due to global warming and environmental concern, research laboratories and pharmaceutical industries around the world are searching for more environmentally friendly reaction conditions for synthesizing

• afford various N-substituted pyrroles 27 in 89–94% yields (Scheme 12). A major advantage of this protocol is that in the case of chiral amines, pyrrole formation proceeds without detectable epimerization. In 2013 Azizi et al. [66] have demonstrated a simple and environmentally friendly protocol for the

• ] demonstrated a mild and environmentally friendly biomimetic Clauson–Kaas synthesis of N-substituted pyrroles 37 through the reaction between various arylamines 36 and 2,5-DMTHF (2) using a sustainable catalyst β-cyclodextrin-SO3H in the nontoxic green solvent H2O without the formation of side products (Scheme

Photoredox catalysis enabling decarboxylative radical cyclization of γ,γ-dimethylallyltryptophan (DMAT) derivatives: formal synthesis of 6,7-secoagroclavine

• Alessio Regni,
• Francesca Bartoccini and
• Giovanni Piersanti

Beilstein J. Org. Chem. 2023, 19, 918–927, doi:10.3762/bjoc.19.70

• accomplish by more conventional procedures, enables the synthesis of ergot alkaloid precursors. In addition, this work describes a mild, environmentally friendly method to activate, reductively and oxidatively, natural carboxylic acids for decarboxylative C–C bond formation by exploiting the same

• are usually more convergent, enabling a more diverse chemical space in a rapid fashion [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15]. Currently, increasing numbers of synthetic chemists are developing photocatalytic processes to make molecules efficiently and in an environmentally friendly

Synthesis of aliphatic nitriles from cyclobutanone oxime mediated by sulfuryl fluoride (SO₂F₂)

• Xian-Lin Chen and
• Hua-Li Qin

Beilstein J. Org. Chem. 2023, 19, 901–908, doi:10.3762/bjoc.19.68

• ) carbon, which leads to side reactions of the alkyl intermediates [14][19][20]. Besides, most of the C(sp2)–C(sp3) reactions employ organic halides or organometallic reagents [21][22][23], which are not environmentally friendly. Recently, based on the activation effect of O-acyloximes on N–O bonds [24][25

Cyclodextrins as building blocks for new materials

• Miriana Kfoury and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2023, 19, 889–891, doi:10.3762/bjoc.19.66

• fact that CDs are nontoxic to humans and to the environment and used to develop greener synthetic routes and strategies, CD-based materials are considered safe and environmentally friendly [18]. This includes, among other characteristics, that they are edible, biodegradable, ecological, and

Synthesis of substituted 8H-benzo[h]pyrano[2,3-f]quinazolin-8-ones via photochemical 6π-electrocyclization of pyrimidines containing an allomaltol fragment

• Constantine V. Milyutin,
• Andrey N. Komogortsev,
• Boris V. Lichitsky,
• Mikhail E. Minyaev and
• Valeriya G. Melekhina

Beilstein J. Org. Chem. 2023, 19, 778–788, doi:10.3762/bjoc.19.58

• systems which are unavailable by other methods. Wherein, usually UV-promoted reactions are environmentally friendly due to the absence of toxic reagents, which is especially perspective in context of green chemistry [9][10]. Thus, studies of the photochemical behavior of organic compounds play an

Honeycomb reactor: a promising device for streamlining aerobic oxidation under continuous-flow conditions

• Masahiro Hosoya,
• Yusuke Saito and
• Yousuke Horiuchi

Beilstein J. Org. Chem. 2023, 19, 752–763, doi:10.3762/bjoc.19.55

• for low-cost and environmentally friendly aerobic oxidation and further optimized it to improve the reaction rate. Reaction optimization for aerobic oxidation under batch conditions Based on entry 3 in Table 1, we next focused on optimizing the reaction to increase the reaction rate (Table 2). Open

Mechanochemical solid state synthesis of copper(I)/NHC complexes with K₃PO₄

• Ina Remy-Speckmann,
• Birte M. Zimmermann,
• Mahadeb Gorai,
• Martin Lerch and
• Johannes F. Teichert

Beilstein J. Org. Chem. 2023, 19, 440–447, doi:10.3762/bjoc.19.34

• challenge for syntheses is the development of green and environmentally friendly routes to access value-added products. One important way to more economical syntheses is the concept of catalysis to avoid stoichiometric amounts of reactants and to design reactions more atom efficient [1][2][3]. However, the

Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone

• Solomiia Borova and
• Robert Luxenhofer

Beilstein J. Org. Chem. 2023, 19, 217–230, doi:10.3762/bjoc.19.21

• ]. Therefore, choosing environmentally benign solvents becomes ever more relevant [27]. Accordingly, some research groups have been also looking for "green" and safer solvents suitable for CROP of 2-oxazolines. "Green" solvents are considered environmentally friendly, less hazardous solvents that make a

• , environmentally friendly, highly stable towards oxidation, yet degrades into water and carbon dioxide [27][38]. Therefore, DLG is an interesting candidate to investigate as solvent for the CROP of 2-oxazolines. Accordingly, in this work, we present the first examples of the successful CROP of POx and discuss the

From amines to (form)amides: a simple and successful mechanochemical approach

• Federico Casti,
• Rita Mocci and
• Andrea Porcheddu

Beilstein J. Org. Chem. 2022, 18, 1210–1216, doi:10.3762/bjoc.18.126

• substantial excess of formyl or acyl sources, often used as a solvent. Mechanochemistry has been established as a powerful tool for the rapid, clean, and environmentally friendly synthesis of organic compounds, avoiding bulk solvent and restrictions of solvent-based chemistry [27][28][29][30][31][32][33][34

Electrogenerated base-promoted cyclopropanation using alkyl 2-chloroacetates

• Kouichi Matsumoto,
• Yuta Hayashi,
• Kengo Hamasaki,
• Mizuki Matsuse,
• Hiyono Suzuki,
• Keiji Nishiwaki and
• Norihito Kawashita

Beilstein J. Org. Chem. 2022, 18, 1116–1122, doi:10.3762/bjoc.18.114

• electrochemical production of cyclopropane derivatives is an environmentally friendly and easy to perform synthetic procedure. Keywords: alkyl 2-chloroacetates; cyclopropane derivatives; divided cell; electro-reduction; Introduction In organic chemistry, cyclopropanes and their related compounds have been

Electrochemical vicinal oxyazidation of α-arylvinyl acetates

• Yi-Lun Li,
• Zhaojiang Shi,
• Tao Shen and
• Ke-Yin Ye

Beilstein J. Org. Chem. 2022, 18, 1026–1031, doi:10.3762/bjoc.18.103

• 200240, China 10.3762/bjoc.18.103 Abstract α-Azidoketones are valuable and versatile building blocks in the synthesis of various bioactive small molecules. Herein, we describe an environmentally friendly and efficient electrochemical vicinal oxyazidation protocol of α-arylvinyl acetates to afford

• water to form the desired product E. According to our 18O labeling experiment, the oxygen source of the newly installed carbonyl group probably originates from the vinyl acetate, not from H2O. Conclusion In summary, we have developed an environmentally friendly and efficient electrochemical oxyazidation