Recent advancements in iodide/phosphine-mediated photoredox radical reactions

• Tinglan Liu,
• Yu Zhou,
• Junhong Tang and
• Chengming Wang

Beilstein J. Org. Chem. 2023, 19, 1785–1803, doi:10.3762/bjoc.19.131

• catalysis has risen to prominence as an incredibly effective methodology, establishing itself as a powerful tool for crafting various C–X (X = C, N, O, F, Cl…) bonds owing to its advantageous traits, such as sustainability, practicality, and environmental compatibility [5]. Despite its broad synthetic

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

C–H bond functionalization: recent discoveries and future directions

• Indranil Chatterjee

Beilstein J. Org. Chem. 2023, 19, 1568–1569, doi:10.3762/bjoc.19.114

• well as famous Noble-prize-winning cross-couplings, therefore approaching another step up towards sustainability. Likewise, a free-radical process is also a classical way to functionalize nonactivated C−H bonds in which site selectivity arises either from the relative strength of the C−H bonds or from

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

• potential of those solvents in many applications (electrodeposition, organic syntheses, biomass extraction, etc.) [11][12]. The more recent ones also deal with the importance of a better characterization of DES [13] and a clear evaluation of their sustainability via life-cycle assessment to evaluate the

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

• 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

Radical ligand transfer: a general strategy for radical functionalization

• David T. Nemoto Jr,
• Kang-Jie Bian,
• Shih-Chieh Kao and
• Julian G. West

Beilstein J. Org. Chem. 2023, 19, 1225–1233, doi:10.3762/bjoc.19.90

• using this step appealing from a sustainability standpoint. While exciting progress has been made, many opportunities remain using this mechanistic approach. Two key areas that could yield exciting advances are combining RLT with new radical-generating elementary steps and the further development of

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

• their biodegradability [4], negligible toxicity, and excellent safety profile [5]. In addition, CDs offer a further step towards sustainability, making them suitable for a wide range of uses in various fields. Accordingly, the global market size of CDs is expected to grow to nearly US$ 390 million by

Cassane diterpenoids with α-glucosidase inhibitory activity from the fruits of Pterolobium macropterum

• Sarot Cheenpracha,
• Ratchanaporn Chokchaisiri,
• Lucksagoon Ganranoo,
• Sareeya Bureekaew,
• Thunwadee Limtharakul and
• Surat Laphookhieo

Beilstein J. Org. Chem. 2023, 19, 658–665, doi:10.3762/bjoc.19.47

• 50200, Thailand Center of Chemical Innovation for Sustainability (CIS) and School of Science, Mae Fah Luang University, Chiang Rai 57100, Thailand Medicinal Plants Innovation Center of Mae Fah Luang University, Chiang Rai 57100, Thailand 10.3762/bjoc.19.47 Abstract Two new cassane diterpenoids, 14β

• °16'51.5"N 100°43'30.3"E) in August 2021 and identified by Mr. Martin van de Bult, Doi Tung Development Project. A voucher specimen (UP-CNP003) was deposited at the Chemistry of Natural Products for Sustainability Laboratory, School of Science, University of Phayao. Extraction and isolation The fresh

Transition-metal-catalyzed C–H bond activation as a sustainable strategy for the synthesis of fluorinated molecules: an overview

• Louis Monsigny,
• Floriane Doche and
• Tatiana Besset

Beilstein J. Org. Chem. 2023, 19, 448–473, doi:10.3762/bjoc.19.35

• derivatives. Finally, the use of abundant non-noble transition metals [209][210][211] in such reactions combined or not with modern technologies (photocatalysis and electrocatalysis) is still underexplored and any advances will be of high importance especially from a sustainability point of view aiming at

Group 13 exchange and transborylation in catalysis

• Dominic R. Willcox and
• Stephen P. Thomas

Beilstein J. Org. Chem. 2023, 19, 325–348, doi:10.3762/bjoc.19.28

• after In‒N/B‒H exchange with HBpin gave a borylimine iron complex 110. A second hydroelementation and In‒N/B‒H exchange gave the bisborylamine 113 and regenerated the HInCl2 107 co-catalyst (Scheme 27). Conclusion Increasing concerns over the sustainability and toxicity of many transition-metal

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

• Chemistry, Department of Chemistry and Helsinki Institute of Sustainability Science, Faculty of Science, University of Helsinki, PO Box 55, 00014 Helsinki, Finland 10.3762/bjoc.19.21 Abstract For about the last ten years, poly(2-oxazoline)s have attracted significant attention as potential material for

• biomedical applications in, e.g., drug delivery systems, tissue engineering and more. Commonly, the synthesis of poly(2-oxazoline)s involves problematic organic solvents that are not ideal from a safety and sustainability point of view. In this study, we investigated the cationic ring-opening polymerization

Modern flow chemistry – prospect and advantage

• Philipp Heretsch

Beilstein J. Org. Chem. 2023, 19, 33–35, doi:10.3762/bjoc.19.3

• scalability, and higher sustainability are the most prevalent ones. To provide examples and explanation for these claims, “flash chemistry”, a term coined by late Yoshida [4] for reactions at the diffusion limit, i.e., reactions completed within milliseconds with proper mixing, showcases the fast heat- and

Inline purification in continuous flow synthesis – opportunities and challenges

• Jorge García-Lacuna and
• Marcus Baumann

Beilstein J. Org. Chem. 2022, 18, 1720–1740, doi:10.3762/bjoc.18.182

• these tools is provided as a guide to aid researchers in selecting the most appropriate approach for future applications. It is hoped that this perspective contributes to new developments in this field in the context of process and cost efficiency, sustainability and industrial uptake of new flow

• opportunities remain for improved and widely applicable inline purification tools where interdisciplinary solutions will impact on the robustness and sustainability of future flow campaigns. Automated in-line chromatography with the Advion puriFlash® system. The rightmost part of the scheme was adapted from [38

Mechanochemical bottom-up synthesis of phosphorus-linked, heptazine-based carbon nitrides using sodium phosphide

• Blaine G. Fiss,
• Georgia Douglas,
• Michael Ferguson,
• Jorge Becerra,
• Jesus Valdez,
• Trong-On Do,
• Tomislav Friščić and
• Audrey Moores

Beilstein J. Org. Chem. 2022, 18, 1203–1209, doi:10.3762/bjoc.18.125

• Discovery Accelerator Supplement, the Canada Foundation for Innovation (CFI), the McGill Sustainability Systems Initiative (MSSI), the Fonds de Recherche du Québec – Nature et Technologies (FRQNT) – Centre for Green Chemistry and Catalysis (CGCC), the Walter C. Sumner Memorial Fellowship (B. G. F.), McGill

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

• catalysts (Pd, Rh, Fe, etc.) were employed to boost the reactivity of NXS (Scheme 1b) [32][33][34][35][36][37][38][39][40][41][42][43]. However, the use of toxic and expensive metals, high catalyst loading, and heating conditions are some sheer hurdles to achieving sustainability. Among notable other

Mechanochemical halogenation of unsymmetrically substituted azobenzenes

• Dajana Barišić,
• Mario Pajić,
• Ivan Halasz,
• Darko Babić and
• Manda Ćurić

Beilstein J. Org. Chem. 2022, 18, 680–687, doi:10.3762/bjoc.18.69

• alternative to conventional solvent-based protocols, offering unique advantages in terms of sustainability, reaction times, yields, reactant solubility, selectivity, and chemical reactivity. Although ball milling methods are widely used for the synthesis of various classes of compounds [26][27][28][29][30][31

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

• method for the production of cyclohexene oxide is highly desired to be developed, taking sustainability for the environment and our society into consideration. The general synthetic procedure for cyclohexene oxide is the epoxidation of cyclohexene [7][8]. Among various oxidizing agents used in the

New advances in asymmetric organocatalysis

• Radovan Šebesta

Beilstein J. Org. Chem. 2022, 18, 240–242, doi:10.3762/bjoc.18.28

• combination of activation modes in bifunctional or multifunctional catalysis. Important is also a “green” aspect of organocatalysis as well as its fruitful overlap with many sustainability ideas [15]. In 2012, there has been a thematic issue of the Beilstein Journal of Organic Chemistry devoted to asymmetric

Earth-abundant 3d transition metals on the rise in catalysis

• Nikolaos Kaplaneris and
• Lutz Ackermann

Beilstein J. Org. Chem. 2022, 18, 86–88, doi:10.3762/bjoc.18.8

• , Germany 10.3762/bjoc.18.8 Keywords: C–H activation; 3d transition metals; green chemistry; late-stage functionalization; sustainability; Transition metal catalysis has emerged as a transformative platform for the assembly of increasingly complex compounds, with enabling applications to natural product

• alternatives. Furthermore, metal-catalyzed cross-couplings do require prefunctionalizations on both substrates and generate stoichiometric quantities of undesired chemical waste, thus reducing the sustainability of these catalytic transformations. To address these major limitations, the past decades have

N-Sulfinylpyrrolidine-containing ureas and thioureas as bifunctional organocatalysts

• Viera Poláčková,
• Dominika Krištofíková,
• Boglárka Némethová,
• Renata Górová,
• Mária Mečiarová and
• Radovan Šebesta

Beilstein J. Org. Chem. 2021, 17, 2629–2641, doi:10.3762/bjoc.17.176

• organocatalysis can benefit and accommodate many sustainability techniques [29]. Mechanochemistry can increase the sustainability profile of a chemical process by reducing potentially harmful organic solvents and bring other benefits such as substantially shortened reaction times. A handful of asymmetric

An initiator- and catalyst-free hydrogel coating process for 3D printed medical-grade poly(ε-caprolactone)

• Jochen Löblein,
• Thomas Lorson,
• Miriam Komma,
• Tobias Kielholz,
• Maike Windbergs,
• Paul D. Dalton and
• Robert Luxenhofer

Beilstein J. Org. Chem. 2021, 17, 2095–2101, doi:10.3762/bjoc.17.136

• Chemistry, Department of Chemistry and Helsinki Institute of Sustainability Science, Faculty of Science, University of Helsinki, 00014 Helsinki, Finland 10.3762/bjoc.17.136 Abstract Additive manufacturing or 3D printing as an umbrella term for various materials processing methods has distinct advantages

Asymmetric organocatalyzed synthesis of coumarin derivatives

• Natália M. Moreira,
• Lorena S. R. Martelli and
• Arlene G. Corrêa

Beilstein J. Org. Chem. 2021, 17, 1952–1980, doi:10.3762/bjoc.17.128

• synthetic perspective, coumarin derivatives have received much attention due to their pivotal role in organic synthesis [16][17][18]. The development of efficient synthetic processes with eco-friendliness and sustainability that avoid the extensive use of toxic and hazardous reagents and solvents, as well

Sustainable manganese catalysis for late-stage C–H functionalization of bioactive structural motifs

• Jongwoo Son

Beilstein J. Org. Chem. 2021, 17, 1733–1751, doi:10.3762/bjoc.17.122

• organic synthesis. Among the 3d metals, manganese catalysts have gained increasing attention for late-stage diversification due to the sustainability, cost-effectiveness, ease of operation, and reduced toxicity. Herein, we summarize recent manganese-catalyzed late-stage C–H functionalization reactions of

• multiple steps to prepare suitable high-valent Mn complexes. Furthermore, Mn(I)-catalyzed enantioselective C–H functionalization at the late stage is still underexplored. Given the sustainability and versatility of manganese-catalyzed late-stage functionalization, further advances are expected in the

Photoinduced post-modification of graphitic carbon nitride-embedded hydrogels: synthesis of 'hydrophobic hydrogels' and pore substructuring

• Cansu Esen and
• Baris Kumru

Beilstein J. Org. Chem. 2021, 17, 1323–1334, doi:10.3762/bjoc.17.92

• ][10][11][12]. The potential of hydrogels is beyond biomaterials, currently these aqueous soft materials are prime candidates in agricultural delivery systems as well [13][14]. In the era of sustainability, utilization of sunlight is of great importance [15]. Metal-containing and mostly toxic and non

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

• flow [86]. Due to the inherently low active volumes of reactants that are processed in the reaction zone within a continuous-flow reactor, the safety risks associated with critical event are greatly diminished. In addition, process reliance and sustainability are further improved by adding extra safety