Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts

• Ritu Mamgain,
• Kokila Sakthivel and
• Fateh V. Singh

Beilstein J. Org. Chem. 2024, 20, 2891–2920, doi:10.3762/bjoc.20.243

• overview of arylation of carbon and heteroatom substrates via diaryliodonium salts in metal-free conditions. This review emphasizes the significance and potential of DIASs in contemporary organic chemistry. Review C-Arylation Over the past decade, there has been a surge of interest in metal-catalyzed C

Synthesis of pyrrole-fused dibenzoxazepine/dibenzothiazepine/triazolobenzodiazepine derivatives via isocyanide-based multicomponent reactions

• Marzieh Norouzi,
• Mohammad Taghi Nazeri,
• Ahmad Shaabani and
• Behrouz Notash

Beilstein J. Org. Chem. 2024, 20, 2870–2882, doi:10.3762/bjoc.20.241

• Marzieh Norouzi Mohammad Taghi Nazeri Ahmad Shaabani Behrouz Notash Department of Organic Chemistry, Shahid Beheshti University, Daneshjou Boulevard, Tehran, 1983969411, Iran Department of Inorganic Chemistry, Shahid Beheshti University, Daneshjou Boulevard, Tehran, 1983969411, Iran 10.3762/bjoc

Synthesis and antimycotic activity of new derivatives of imidazo[1,2-a]pyrimidines

• Dmitriy Yu. Vandyshev,
• Daria A. Mangusheva,
• Khidmet S. Shikhaliev,
• Kirill A. Scherbakov,
• Oleg N. Burov,
• Alexander D. Zagrebaev,
• Tatiana N. Khmelevskaya,
• Alexey S. Trenin and
• Fedor I. Zubkov

Beilstein J. Org. Chem. 2024, 20, 2806–2817, doi:10.3762/bjoc.20.236

• Dmitriy Yu. Vandyshev Daria A. Mangusheva Khidmet S. Shikhaliev Kirill A. Scherbakov Oleg N. Burov Alexander D. Zagrebaev Tatiana N. Khmelevskaya Alexey S. Trenin Fedor I. Zubkov Organic Chemistry Department, Voronezh State University, 1 Universitetskaya pl., 394018 Voronezh, Russian Federation

• St., 344090 Rostov-on-Don, Russian Federation Clinical Laboratory Diagnostics Department, N. N. Burdenko Voronezh State Medical University, 10 Studencheskaya St., 394036 Voronezh, Russian Federation Gause Institute of New Antibiotics, 11 B. Pirogovskaya St., 119021 Moscow, Russian Federation Organic

• Chemistry Department, RUDN University, 6 Miklukho-Maklaya St., 117198 Moscow, Russian Federation 10.3762/bjoc.20.236 Abstract The heterocyclic core of imidazo[1,2-a]pyrimidine was formed in satisfactory yields as a result of the interaction of the readily available 2-aminoimidazole with N-substituted

Mechanochemical difluoromethylations of ketones

• Jinbo Ke,
• Pit van Bonn and
• Carsten Bolm

Beilstein J. Org. Chem. 2024, 20, 2799–2805, doi:10.3762/bjoc.20.235

• Jinbo Ke Pit van Bonn Carsten Bolm Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany 10.3762/bjoc.20.235 Abstract We present a mechanochemical synthesis of difluoromethyl enol ethers. Utilizing an in situ generation of difluorocarbenes, ketones are

C–C Coupling in sterically demanding porphyrin environments

• Liam Cribbin,
• Brendan Twamley,
• Nicolae Buga,
• John E. O’ Brien,
• Raphael Bühler,
• Roland A. Fischer and
• Mathias O. Senge

Beilstein J. Org. Chem. 2024, 20, 2784–2798, doi:10.3762/bjoc.20.234

• Liam Cribbin Brendan Twamley Nicolae Buga John E. O' Brien Raphael Buhler Roland A. Fischer Mathias O. Senge School of Chemistry, Chair of Organic Chemistry, Trinity Biomedical Sciences Institute, 152-160 Pearse Street, Trinity College Dublin, The University of Dublin, Dublin, D02 R590, Ireland

Copper-catalyzed yne-allylic substitutions: concept and recent developments

• Shuang Yang and
• Xinqiang Fang

Beilstein J. Org. Chem. 2024, 20, 2739–2775, doi:10.3762/bjoc.20.232

• method to access structurally diverse chiral coumarin derivatives, which are of great interest in the fields of medicinal chemistry and synthetic organic chemistry (Scheme 22, 22a–y). Moreover, the utilization of 2-(1-ethoxyethylidene)malononitrile as a γ-nucleophile yielded the desired product 22z with

Young investigators in natural products chemistry, biosynthesis, and enzymology

• Jeffrey D. Rudolf,
• Lena Barra and
• Takayoshi Awakawa

Beilstein J. Org. Chem. 2024, 20, 2720–2721, doi:10.3762/bjoc.20.229

• also humbly thank Prof. Jeroen Dickschat for inviting each of us to guest-edit this wonderful issue featuring rising stars in the field of natural products. Finally, we thank the staff of the Beilstein Journal of Organic Chemistry for making this issue possible. As you browse this issue, we hope that

5th International Symposium on Synthesis and Catalysis (ISySyCat2023)

• Anthony J. Burke and
• Elisabete P. Carreiro

Beilstein J. Org. Chem. 2024, 20, 2704–2707, doi:10.3762/bjoc.20.227

• ://isysycat2025.events.chemistry.pt/), and we hope that it will attract the attention of colleagues and practitioners from all corners of the world, who will share in the rich chemistry to be discussed during those four days. As a final remark, we are very grateful to the Beilstein Journal of Organic Chemistry

The scent gland composition of the Mangshan pit viper, Protobothrops mangshanensis

• Jonas Holste,
• Paul Weldon,
• Donald Boyer and
• Stefan Schulz

Beilstein J. Org. Chem. 2024, 20, 2644–2654, doi:10.3762/bjoc.20.222

• Jonas Holste Paul Weldon Donald Boyer Stefan Schulz Institute of Organic Chemistry, Technische Universität Braunschweig, 38106 Braunschweig, Germany Smithsonian Conservation Biology Institute, National Zoological Park, 1500 Remount Road, Front Royal, Virginia 22630, USA Bronx Zoo, 2300 Southern

Base-promoted cascade recyclization of allomaltol derivatives containing an amide fragment into substituted 3-(1-hydroxyethylidene)tetronic acids

• Andrey N. Komogortsev,
• Constantine V. Milyutin and
• Boris V. Lichitsky

Beilstein J. Org. Chem. 2024, 20, 2585–2591, doi:10.3762/bjoc.20.217

• Andrey N. Komogortsev Constantine V. Milyutin Boris V. Lichitsky N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Pr., 47, Moscow, 119991, Russian Federation 10.3762/bjoc.20.217 Abstract For the first time, recyclization of allomaltol derivatives with an amide

• , copies of NMR spectra, X-ray crystallographic data and refinement details. Supporting Information File 142: Analytical data of all compounds 4, 7 and 9. Acknowledgements Crystal structure determination was performed in the Department of Structural Studies of Zelinsky Institute of Organic Chemistry

Transition-metal-free synthesis of arylboronates via thermal generation of aryl radicals from triarylbismuthines in air

• Yuki Yamamoto,
• Yuki Konakazawa,
• Kohsuke Fujiwara and
• Akiya Ogawa

Beilstein J. Org. Chem. 2024, 20, 2577–2584, doi:10.3762/bjoc.20.216

• of organobismuth compounds in synthetic organic chemistry. Further applications of organobismuth compounds as aryl radical precursors are currently under investigation. Experimental General comments: Unless otherwise stated, all starting materials were purchased from commercial sources and used

A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

• Nian Li,
• Ruzal Sitdikov,
• Ajit Prabhakar Kale,
• Joost Steverlynck,
• Bo Li and
• Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

• , 52074, Aachen, Germany 10.3762/bjoc.20.214 Abstract With the resurgence of electrosynthesis in organic chemistry, there is a significant increase in the number of routes available for late-stage functionalization (LSF) of drugs. Electrosynthetic methods, which obviate the need for hazardous chemical

• . Review 1 LSF via anodic oxidation To date, the majority of electrosynthetic methods in organic chemistry consists of anodic oxidations. These techniques are generally more robust and can often be performed outside of a glovebox, making them particularly attractive for larger scale applications in

Visible-light-mediated flow protocol for Achmatowicz rearrangement

• Joachyutharayalu Oja,
• Sanjeev Kumar and
• Srihari Pabbaraja

Beilstein J. Org. Chem. 2024, 20, 2493–2499, doi:10.3762/bjoc.20.213

• ; photocatalyst; sunlight; Introduction The furan ring moiety is present in several natural products [1] and serves as a key precursor to 1,4-dicarbonyls [2], cyclopentanones [3], and carboxylic acids [4], in synthetic organic chemistry. Furfuryl alcohols, a family of 2-substituted furan molecules, are

Tandem diazotization/cyclization approach for the synthesis of a fused 1,2,3-triazinone-furazan/furoxan heterocyclic system

• Yuri A. Sidunets,
• Valeriya G. Melekhina and
• Leonid L. Fershtat

Beilstein J. Org. Chem. 2024, 20, 2342–2348, doi:10.3762/bjoc.20.200

• Yuri A. Sidunets Valeriya G. Melekhina Leonid L. Fershtat N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Leninsky Prospect, 47, Moscow, Russian Federation National Research University Higher School of Economics 101000, Myasnitskaya str., 20, Moscow, Russian

• the Department of Structural Studies of Zelinsky Institute of Organic Chemistry. Funding This work was supported by the Russian Science Foundation (grant 23-43-00090).

Catalysing (organo-)catalysis: Trends in the application of machine learning to enantioselective organocatalysis

• Stefan P. Schmid,
• Leon Schlosser,
• Frank Glorius and
• Kjell Jorner

Beilstein J. Org. Chem. 2024, 20, 2280–2304, doi:10.3762/bjoc.20.196

• reduce the number of required experiments. As such, these methods contribute to the acceleration of catalyst discovery, for example through high-throughput virtual screening. Predating these computational techniques is the desire to understand and explain experimental outcomes in organic chemistry with

• a major challenge in organic chemistry and restricts the applicability of literature data for statistical modelling [30]. Despite emerging high-throughput experimentation (HTE) pipelines [44][45], large datasets of high-quality are still scarce. While multiple large datasets are available for

• physical organic chemistry with data-driven analysis techniques, in particular MLR, to gain a greater understanding of the enantioselectivity-determining steps for a C–N coupling catalysed by CPA derivatives (Figure 15A) [143]. Based on their findings that π–π interactions between the catalyst’s triazole

Natural resorcylic lactones derived from alternariol

• Joachim Podlech

Beilstein J. Org. Chem. 2024, 20, 2171–2207, doi:10.3762/bjoc.20.187

• Joachim Podlech Karlsruhe Institute of Technology (KIT), Institute of Organic Chemistry, Kaiserstraße 12, 76131 Karlsruhe, Germany 10.3762/bjoc.20.187 Abstract In this overview, naturally occurring resorcylic lactones biosynthetically derived from alternariol and almost exclusively produced by

O,S,Se-containing Biginelli products based on cyclic β-ketosulfone and their postfunctionalization

• Kateryna V. Dil and
• Vitalii A. Palchykov

Beilstein J. Org. Chem. 2024, 20, 2143–2151, doi:10.3762/bjoc.20.184

• Foundation for financial support for the presentation of this work at the 15th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-15, November 20–23, 2023, Kyoto, Japan). In addition, last but not least, we thank all brave defenders of Ukraine that made finalizing this work possible

Factors influencing the performance of organocatalysts immobilised on solid supports: A review

• Zsuzsanna Fehér,
• Dóra Richter,
• Gyula Dargó and
• József Kupai

Beilstein J. Org. Chem. 2024, 20, 2129–2142, doi:10.3762/bjoc.20.183

• Zsuzsanna Feher Dora Richter Gyula Dargo Jozsef Kupai Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Műegyetem rkp. 3., H-1111 Budapest, Hungary 10.3762/bjoc.20.183 Abstract Organocatalysis has become a powerful tool in synthetic chemistry

• applications in organic chemistry. Keywords: asymmetric synthesis; catalyst recycling; heterogenisation; organocatalysis; solid support; Introduction Organocatalysts are small molecules that do not contain a metal atom in the reaction centre and are able to increase the speed of reactions. They have proven

Efficacy of radical reactions of isocyanides with heteroatom radicals in organic synthesis

• Akiya Ogawa and
• Yuki Yamamoto

Beilstein J. Org. Chem. 2024, 20, 2114–2128, doi:10.3762/bjoc.20.182

• reaction of carbon radicals with isocyanides generates imidoyl radicals as key active species [12], and addition and cyclization reactions using these radical species are useful in synthetic organic chemistry, especially multicomponent synthesis. If various functional groups can be appropriately attached

• metal complex or functional dye as a photocatalyst (PC) [19][20]. Recently, some important reviews summarize and discuss the use of method 3 in synthetic organic chemistry [21][22]; in contrast, there is little detailed and coherent literature on the overall research trends regarding the latest research

Harnessing the versatility of hydrazones through electrosynthetic oxidative transformations

• Aurélie Claraz

Beilstein J. Org. Chem. 2024, 20, 1988–2004, doi:10.3762/bjoc.20.175

• (Scheme 26) [76]. Electrochemical access to diazo compounds Diazo compounds are highly useful synthetic reagents in organic chemistry. For instance, they are regularly utilized as 1,3-dipoles in cycloaddition reactions or as precursor of carbenes under thermal, photochemical, and catalytic transition

1,2-Difluoroethylene (HFO-1132): synthesis and chemistry

• Liubov V. Sokolenko,
• Taras M. Sokolenko and
• Yurii L. Yagupolskii

Beilstein J. Org. Chem. 2024, 20, 1955–1966, doi:10.3762/bjoc.20.171

• Liubov V. Sokolenko Taras M. Sokolenko Yurii L. Yagupolskii Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Academician Kukhar str., 5, Kyiv-94, 02660, Ukraine 10.3762/bjoc.20.171 Abstract This article provides a comprehensive overview of the synthesis and chemistry of

• . Photochemical [2 + 2]-cycloaddition with fluorinated aldehydes and ketones gives access to a variety of fluorinated oxygen-containing heterocycles. We hope that this article will help chemists to utilize HFO-1132 and that this olefin will find applications as a useful synthon in organic chemistry. 1,2

Solvent-dependent chemoselective synthesis of different isoquinolinones mediated by the hypervalent iodine(III) reagent PISA

• Ze-Nan Hu,
• Yan-Hui Wang,
• Jia-Bing Wu,
• Ze Chen,
• Dou Hong and
• Chi Zhang

Beilstein J. Org. Chem. 2024, 20, 1914–1921, doi:10.3762/bjoc.20.167

• Ze-Nan Hu Yan-Hui Wang Jia-Bing Wu Ze Chen Dou Hong Chi Zhang State Key Laboratory of Elemento-Organic Chemistry, The Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, 94 Weijin Road, Tianjin 300071, P. R. China 10.3762/bjoc.20.167 Abstract Isoquinolinone

Electrochemical radical cation aza-Wacker cyclizations

• Sota Adachi and
• Yohei Okada

Beilstein J. Org. Chem. 2024, 20, 1900–1905, doi:10.3762/bjoc.20.165

• organic chemistry [11][12][13][14][15]. Single-electron oxidation of bench-stable substrates can generate radical cations that offer unique reactivities as intermediates for various bond-formation processes (also true for reduction). Because the reactivities of radicals and ions are fundamentally

2-Heteroarylethylamines in medicinal chemistry: a review of 2-phenethylamine satellite chemical space

• Carlos Nieto,
• Alejandro Manchado,
• Ángel García-González,
• David Díez and
• Narciso M. Garrido

Beilstein J. Org. Chem. 2024, 20, 1880–1893, doi:10.3762/bjoc.20.163

• Carlos Nieto Alejandro Manchado Angel Garcia-Gonzalez David Diez Narciso M. Garrido Department of Organic Chemistry, Faculty of Chemical Sciences, University of Salamanca, Pl. Caídos, s/n, 37008 Salamanca, Spain 10.3762/bjoc.20.163 Abstract The concept of bioisostere replacement is of paramount

A facile three-component route to powerful 5-aryldeazaalloxazine photocatalysts

• Ivana Weisheitelová,
• Radek Cibulka,
• Marek Sikorski and
• Tetiana Pavlovska

Beilstein J. Org. Chem. 2024, 20, 1831–1838, doi:10.3762/bjoc.20.161

• Ivana Weisheitelova Radek Cibulka Marek Sikorski Tetiana Pavlovska Department of Organic Chemistry, University of Chemistry and Technology, Prague, Czech Republic Faculty of Chemistry, Adam Mickiewicz University, Poznań, Poland 10.3762/bjoc.20.161 Abstract Functionalized 5-aryldeazaalloxazines

• 2, as demonstrated in our previous studies with 5-aryldeazaflavins 1 [14][15][16][17][18]. Multicomponent reactions (MCRs) remain a powerful strategy in synthetic organic chemistry due to their widespread applications in drug discovery. By offering significant advantages over conventional, linear