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

• field of organic synthesis. These compounds are readily accessible, safe, and more stable than toxic, unstable, and foul-smelling thiols. These electrophilic sulfur sources have deserved particular interest for the C–S bond formation via the reaction with various nucleophiles. Their preparation is

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

• method allows the efficient alkylation of aromatic rings, can directly afford pharmaceutically significant heterocycles, and the raw materials and iron catalysts are safe and readily available. In 2017, Xu, Loh, and co-workers, demonstrated an iron-catalyzed hydroalkylation reaction of α,β-unsaturated

• 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

• of water (Table 1, entries 1 and 2), the addition of oxygen (entries 1, 5, and 6) and light in the UV-A region (entries 8 and 9) turned out to be crucial (see Supporting Information File 1, Table S2). Additives With the ultimate goal in mind to develop a safe and scalable protocol in continuous flow

• short reaction times. Additionally, benign additives can further enhance the reaction rate. Finally, the protocol was transferred to a continuous-flow setup, making the method scalable and drastically more safe, and thus appealing for implementation in commercial production processes. Study of additives

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

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

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

• , not only a unique control of reaction parameters, such as improved mass and heat transfer, but also reduced safety risks and increased reproducibility of the results [29][35][36]. These features should therefore allow us to scale up our directed C3-functionalizations of furfurylimines under safe

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

• bio-based solvent obtained from cellulose [36][37], commercially known as CyreneTM, and has been introduced as a new "green" solvent marketed specifically as an alternative to solvents such as DMF or NMP, which are particularly interesting for CROP of POx. It is reported that DLG is safe to handle

Insight into oral amphiphilic cyclodextrin nanoparticles for colorectal cancer: comprehensive mathematical model of drug release kinetic studies and antitumoral efficacy in 3D spheroid colon tumors

• Sedat Ünal,
• Gamze Varan,
• Juan M. Benito,
• Yeşim Aktaş and
• Erem Bilensoy

Beilstein J. Org. Chem. 2023, 19, 139–157, doi:10.3762/bjoc.19.14

• in cancer-related deaths. With the current treatment possibilities, a definitive, safe, and effective treatment approach for CRC has not been presented yet. However, new drug delivery systems show promise in this field. Amphiphilic cyclodextrin-based nanocarriers are innovative and interesting

New triazole-substituted triterpene derivatives exhibiting anti-RSV activity: synthesis, biological evaluation, and molecular modeling

• Elenilson F. da Silva,
• Krist Helen Antunes Fernandes,
• Denise Diedrich,
• Jessica Gotardi,
• Marcia Silvana Freire Franco,
• Carlos Henrique Tomich de Paula da Silva,
• Ana Paula Duarte de Souza and
• Simone Cristina Baggio Gnoatto

Beilstein J. Org. Chem. 2022, 18, 1524–1531, doi:10.3762/bjoc.18.161

• , selective, and potent anti-HIV activity, however, it failed in phase IIb clinical trials due to viral resistance [28][29][30][31]. Even so, this class of natural products has great antiviral potential and its chemical modification could lead to new, efficient, and safe therapeutic resources. In this

A one-pot electrochemical synthesis of 2-aminothiazoles from active methylene ketones and thioureas mediated by NH₄I

• Shang-Feng Yang,
• Pei Li,
• Zi-Lin Fang,
• Sen Liang,
• Hong-Yu Tian,
• Bao-Guo Sun,
• Kun Xu and
• Cheng-Chu Zeng

Beilstein J. Org. Chem. 2022, 18, 1249–1255, doi:10.3762/bjoc.18.130

• . Organic electrosynthesis has been recognized as a green, modern, and safe technique, since electrons can be used as an alternative for oxidants or reductants [30][31][32][33][34][35][36][37][38]. During our continuous interests in halide-mediated indirect electrolysis [39][40][41][42], we have achieved

Electro-conversion of cumene into acetophenone using boron-doped diamond electrodes

• Mana Kitano,
• Tsuyoshi Saitoh,
• Shigeru Nishiyama,
• Yasuaki Einaga and
• Takashi Yamamoto

Beilstein J. Org. Chem. 2022, 18, 1154–1158, doi:10.3762/bjoc.18.119

• , where the BDD’s wide potential window enables the direct anodic oxidation of cumene into the cumyl cation. Since electricity is directly employed as the oxidizing and reducing reagents, the present protocol is easy to use, suitable for scale-up, and inherently safe. Keywords: aromatic alkyl; boron

A versatile way for the synthesis of monomethylamines by reduction of N-substituted carbonylimidazoles with the NaBH₄/I₂ system

• Lin Chen,
• Xuan Zhou,
• Zhiyong Chen,
• Changxu Wang,
• Shunjie Wang and
• Hanbing Teng

Beilstein J. Org. Chem. 2022, 18, 1032–1039, doi:10.3762/bjoc.18.104

• materials including amines, carboxylic acids and isocyanates under mild and safe reaction conditions. Results and Discussion Initially, N-phenethyl-1H-imidazole-1-carboxamide (1b) was chosen as a model substrate to react with 3.0 equiv of NaBH4 and 1.0 equiv of I2 in THF at reflux temperature, as expected

Automated grindstone chemistry: a simple and facile way for PEG-assisted stoichiometry-controlled halogenation of phenols and anilines using N-halosuccinimides

• Dharmendra Das,
• Akhil A. Bhosle,
• Amrita Chatterjee and
• Mainak Banerjee

Beilstein J. Org. Chem. 2022, 18, 999–1008, doi:10.3762/bjoc.18.100

• (X = Br, Cl) suffers from low atom economy (<50%), formation of corrosive byproducts (e.g., HBr) [15][16], which cause serious environmental issues. To mitigate the problem, several mild and operationally safe halogenating agents have been successfully introduced to replace X2 [17][18][19][20][21][22

Synthesis of odorants in flow and their applications in perfumery

• Merlin Kleoff,
• Paul Kiler and
• Philipp Heretsch

Beilstein J. Org. Chem. 2022, 18, 754–768, doi:10.3762/bjoc.18.76

• safe two-step synthesis of 56 from cyclohexanone. In the first step, a solution of cyclohexanone in dodecane is mixed in a Q-piece with hydrogen peroxide, nitric acid, and formic acid and subsequently pumped at room temperature through a PTFE tube reactor with a residence time of 93 min. The resulting

Rapid gas–liquid reaction in flow. Continuous synthesis and production of cyclohexene oxide

• Kyoko Mandai,
• Tetsuya Yamamoto,
• Hiroki Mandai and
• Aiichiro Nagaki

Beilstein J. Org. Chem. 2022, 18, 660–668, doi:10.3762/bjoc.18.67

• for safe, low-cost, and environmentally benign operations. Initially, we decided to maintain the key flow conditions such as the flow rate since it severely affects the fluidic interaction inside a flow reactor and thus the reaction efficiency of this type of gas–liquid reaction. Thus, the flow rate

Synthesis of sulfur karrikin bioisosteres as potential neuroprotectives

• Martin Pošta,
• Václav Zima,
• Lenka Poštová Slavětínská,
• Marika Matoušová and
• Petr Beier

Beilstein J. Org. Chem. 2022, 18, 549–554, doi:10.3762/bjoc.18.57

• unknown, that could have untapped potential in medicine. The study of the relationship between the components of plant-derived smoke and MAO and/or AChE can lead to safe and efficient drugs and drug scaffolds from a yet unexploited resource. One very important bioactive constituent of smoke of burning

Ready access to 7,8-dihydroindolo[2,3-d][1]benzazepine-6(5H)-one scaffold and analogues via early-stage Fischer ring-closure reaction

• Irina Kuznetcova,
• Felix Bacher,
• Daniel Vegh,
• Hsiang-Yu Chuang and
• Vladimir B. Arion

Beilstein J. Org. Chem. 2022, 18, 143–151, doi:10.3762/bjoc.18.15

• was observed by TLC. However, the acid chloride reacted very sluggishly with (CH3)3SiCHN2, which is a safe alternative to the highly explosive diazomethane [34]. Another attempt to synthesize the open-chain precursor from indole and 2-bromo-N-(2-bromophenyl)acetamide by regioselective palladium

Host–guest interaction and properties of cucurbit[8]uril with chloramphenicol

• Lin Zhang,
• Jun Zheng,
• Guangyan Luo,
• Xiaoyue Li,
• Yunqian Zhang,
• Zhu Tao and
• Qianjun Zhang

Beilstein J. Org. Chem. 2021, 17, 2832–2839, doi:10.3762/bjoc.17.194

• cucurbit[n]urils can be used as non-toxic and safe drug carriers [29][30][31], among which cucurbit[8]uril (Q[8]) [32] has a large cavity. Q[8] interacts with a variety of small drug molecules such as chrysin, oroxin A and B, baicalein, etc., which can enhance the solubility, stability, antioxidant and

Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

• Umesh P. Aher,
• Dhananjai Srivastava,
• Girij P. Singh and
• Jayashree B. S

Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182

Cryogels: recent applications in 3D-bioprinting, injectable cryogels, drug delivery, and wound healing

• Luke O. Jones,
• Leah Williams,
• Tasmin Boam,
• Martin Kalmet,
• Chidubem Oguike and
• Fiona L. Hatton

Beilstein J. Org. Chem. 2021, 17, 2553–2569, doi:10.3762/bjoc.17.171

• injecting through a conventional needle [18]. Gelatin was chosen for its inherent peptide sequences that facilitate cell adhesion and enzymatic degradation. Gelatin is also low cost and safe to use in human testing as shown in a work done by Nichol et al. [77]. The bulk mechanical behaviour, structure, and

• effective but is below the level considered toxic [85]. Drug-delivery systems (DDS) demand safe and effective treatment, and in the majority of cases a long-term target specific treatment would be favoured over general multi-dose pharmaceuticals. Cryogels have been identified as a good material of choice

Towards new NIR dyes for free radical photopolymerization processes

• Haifaa Mokbel,
• Guillaume Noirbent,
• Didier Gigmes,
• Frédéric Dumur and
• Jacques Lalevée

Beilstein J. Org. Chem. 2021, 17, 2067–2076, doi:10.3762/bjoc.17.133

• and safe near-infrared (NIR) light is still the subject of intense research efforts but remains a huge challenge due to the associated low photon energy (wavelength from 0.78 to 2.5 µm). In this study, a series of 17 NIR dyes mainly based on a well-established cyanine scaffold is proposed. Remarkably

• ][4][5][6][7][8]. In this context, the use of NIR light is very attractive, i.e., such a long wavelength is quite safe and characterized by an excellent penetration in materials. Interestingly, NIR curing technology exhibit several advantages: i) an efficient process: a high polymerization rate

Development of N-F fluorinating agents and their fluorinations: Historical perspective

• Teruo Umemoto,
• Yuhao Yang and
• Gerald B. Hammond

Beilstein J. Org. Chem. 2021, 17, 1752–1813, doi:10.3762/bjoc.17.123

• agents for many years. However, these reagents have significant risks for safe handling. Although XeF2 [15] was considered as a safer alternative, it is expensive because of the scarcity of Xe in nature. The appearance of the safe and easy-to-handle N-F fluorinating agents described in this review have

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

• commercial flow reactors allow for the safe simulation of larger scale processes within the lab environment, facilitating and expediting the process optimisation experience. While some of the implications of the flow chemistry are more obvious than others, i.e., greener processes with potential cost

Nitroalkene reduction in deep eutectic solvents promoted by BH₃NH₃

• Chiara Faverio,
• Monica Fiorenza Boselli,
• Patricia Camarero Gonzalez,
• Alessandra Puglisi and
• Maurizio Benaglia

Beilstein J. Org. Chem. 2021, 17, 1041–1047, doi:10.3762/bjoc.17.83

• safe as well as economically and environmentally sustainable alternative to the traditional organic solvents. Here, we report the combination of an atom-economic, very convenient and inexpensive reagent, such as BH3NH3, with bio-based eutectic mixtures as biorenewable solvents in the synthesis of

• whole research community concerned with the concept of a circular economy [3]. In this context, deep eutectic solvents (DESs) have attracted an increasing attention as green, safe, economically and environmentally sustainable alternative to the traditional organic solvents [4]. They are combinations of

• materials that can be used to form eutectic mixtures offers an incredibly high variety of combinations to generate new, safe and biodegradable DESs [5]. Another fundamental principle of green chemistry is the atom economy concept. In this context, ammonia borane (AB) is receiving increasing attention as

Synthetic accesses to biguanide compounds

• Oleksandr Grytsai,
• Cyril Ronco and
• Rachid Benhida

Beilstein J. Org. Chem. 2021, 17, 1001–1040, doi:10.3762/bjoc.17.82

• biguanides. This pathway is particularly convenient as cyanoguanidines are readily available, inexpensive, and safe [32]. Moreover, this reaction occurs with full atom economy and provides the desired biguanides with fairly high yields. A prior step of substituted cyanoguanidine preparation gives access to