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

Oxidation of benzylic alcohols to carbonyls using N-heterocyclic stabilized λ³-iodanes

• Thomas J. Kuczmera,
• Pim Puylaert and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2024, 20, 1677–1683, doi:10.3762/bjoc.20.149

• )iodane is proposed as the reactive intermediate. Keywords: alcohol oxidation; hypervalent iodine; N-heterocycles; Introduction The oxidation of alcohols to aldehydes and ketones is an essential transformation in organic chemistry [1][2]. Generating aldehydes is particularly challenging as they are

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

• strain; Introduction Identifying efficient methods for the preparation of densely functionalized molecules is one of the central goals of modern organic chemistry. In this context, application of strained molecules has garnered increasing attention due to their intrinsic reactivity [1][2]. However

Tetrabutylammonium iodide-catalyzed oxidative α-azidation of β-ketocarbonyl compounds using sodium azide

• Christopher Mairhofer,
• David Naderer and
• Mario Waser

Beilstein J. Org. Chem. 2024, 20, 1510–1517, doi:10.3762/bjoc.20.135

• Christopher Mairhofer David Naderer Mario Waser Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstrasse 69, 4040 Linz, Austria 10.3762/bjoc.20.135 Abstract We herein report the oxidative α-azidation of carbonyl compounds by using NaN3 in the presence of dibenzoyl

Towards an asymmetric β-selective addition of azlactones to allenoates

• Behzad Nasiri,
• Ghaffar Pasdar,
• Paul Zebrowski,
• Katharina Röser,
• David Naderer and
• Mario Waser

Beilstein J. Org. Chem. 2024, 20, 1504–1509, doi:10.3762/bjoc.20.134

• Behzad Nasiri Ghaffar Pasdar Paul Zebrowski Katharina Roser David Naderer Mario Waser Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstrasse 69, 4040 Linz, Austria Department of Chemistry, Faculty of Science, University of Kurdistan, 66177-15175 Sanandaj, Kurdistan

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

• synthesis; electrophotocatalysis; radical decarboxylation; Introduction Alkylnitriles and their derivatives are widely found in pharmaceuticals and biologically active compounds [1][2][3]. In addition, within the field of synthetic organic chemistry, nitriles are synthetically useful handles that can be

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

• Yingbo Shao Zhiyuan Ren Zhihui Han Li Chen Yao Li Xiao-Song Xue State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. China Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry

• become staples in organic chemistry, the exploration of their isoelectronic counterparts, namely hypervalent bromine(III) and chlorine(III) reagents, has been relatively limited, partly due to challenges in synthesizing and stabilizing these compounds. In this study, we conduct a thorough examination of

Rapid construction of tricyclic tetrahydrocyclopenta[4,5]pyrrolo[2,3-b]pyridine via isocyanide-based multicomponent reaction

• Xiu-Yu Chen,
• Ying Han,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2024, 20, 1436–1443, doi:10.3762/bjoc.20.126

• reaction with 5,6-unsubstituted 1,4-dihydropyridine. Keywords: [3 + 2] cycloaddition; cyclopenta-1,3-diene; cyclopenta[4,5]pyrrolo[2,3-b]pyridine; 1,4-dihydropyridine; electron-deficient alkyne; isocyanide; Introduction Isocyanide is a unique and attractive functional group in organic chemistry. The

• been known as indispensable building blocks in modern organic chemistry. Many isocyanide-based carbon–carbon and carbon–heteroatom bond forming reactions have been developed in fascinating ways over the past decades [4][5][6]. The famous multicomponent reactions such as Passerini reaction, Ugi reaction

Synthesis of substituted triazole–pyrazole hybrids using triazenylpyrazole precursors

• Simone Gräßle,
• Laura Holzhauer,
• Nicolai Wippert,
• Olaf Fuhr,
• Martin Nieger,
• Nicole Jung and
• Stefan Bräse

Beilstein J. Org. Chem. 2024, 20, 1396–1404, doi:10.3762/bjoc.20.121

• , 76131 Karlsruhe, Germany Karlsruhe Nano Micro Facility (KNMFi), Karlsruhe Institute of Technology, Kaiserstraße 12, 76131 Karlsruhe, Germany Department of Chemistry, University of Helsinki, P.O. Box 55 (A. I. Virtasen aukio 1), 00014 Helsinki, Finland Institute of Organic Chemistry, Karlsruhe Institute

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

• aldehyde molecules, forming an alcohol and an acid [1][2][3][4]. Since its discovery in 1853, the Cannizzaro reaction has emerged as an important reaction in synthetic organic chemistry with intermolecular, crossed, and intramolecular versions as demonstrated by numerous applications. Notably, the

• important in synthetic organic chemistry due to its ability to provide a convenient route for the synthesis of alcohols and carboxylic acids from aldehydes. This disproportionation reaction has evoked numerous developments and applications. The Cannizzaro reaction proved to be particularly valuable in cases

• '-biphenyl-2,2',6,6'-tetracarboxaldehyde (101) (Scheme 28). Conclusion The Cannizzaro reaction is one of the oldest reactions in organic chemistry for the synthesis of acid and alcohol functionalities through disproportionation reaction of non-enlizable aldehydes. Apart from the conventional methods, several

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

• 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 of 1,2,3-triazoles containing an allomaltol moiety from substituted pyrano[2,3-d]isoxazolones via base-promoted Boulton–Katritzky rearrangement

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

Beilstein J. Org. Chem. 2024, 20, 1334–1340, doi:10.3762/bjoc.20.117

• Constantine V. Milyutin Andrey N. Komogortsev Boris V. Lichitsky N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Pr., 47, Moscow, 119991, Russian Federation 10.3762/bjoc.20.117 Abstract For the first time, the interaction of aroyl containing pyrano[2,3-d

• File 96: Experimental procedures, characterization data of all products, copies of 1H, 13C NMR, spectra of all new compounds, and X-ray crystallographic data. Acknowledgements The crystal structure determination was performed in the Department of Structural Studies of Zelinsky Institute of Organic

• Chemistry, Moscow.

Phenotellurazine redox catalysts: elements of design for radical cross-dehydrogenative coupling reactions

• Alina Paffen,
• Christopher Cremer and
• Frederic W. Patureau

Beilstein J. Org. Chem. 2024, 20, 1292–1297, doi:10.3762/bjoc.20.112

• Alina Paffen Christopher Cremer Frederic W. Patureau Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany 10.3762/bjoc.20.112 Abstract Redox active phenotellurazine catalysts have been recently utilized in two different cross-dehydrogenative coupling

Bismuth(III) triflate: an economical and environmentally friendly catalyst for the Nazarov reaction

• Manoel T. Rodrigues Jr.,
• Aline S. B. de Oliveira,
• Ralph C. Gomes,
• Amanda Soares Hirata,
• Lucas A. Zeoly,
• Hugo Santos,
• João Arantes,
• Catarina Sofia Mateus Reis-Silva,
• João Agostinho Machado-Neto,
• Leticia Veras Costa-Lotufo and
• Fernando Coelho

Beilstein J. Org. Chem. 2024, 20, 1167–1178, doi:10.3762/bjoc.20.99

• ; indanones; Nazarov reaction; Introduction Natural products are the source of inspiration for several research groups that develop new synthetic methodologies. The chemistry of five-membered rings plays an important role in organic chemistry, both because of the wide occurrence in nature [1][2][3][4][5][6

Mild and efficient synthesis and base-promoted rearrangement of novel isoxazolo[4,5-b]pyridines

• Vladislav V. Nikol’skiy,
• Mikhail E. Minyaev,
• Maxim A. Bastrakov and
• Alexey M. Starosotnikov

Beilstein J. Org. Chem. 2024, 20, 1069–1075, doi:10.3762/bjoc.20.94

• Vladislav V. Nikol'skiy Mikhail E. Minyaev Maxim A. Bastrakov Alexey M. Starosotnikov N.D. Zelinsky Institute of Organic Chemistry RAS, Leninsky prosp. 47, 119991 Moscow, Russia 10.3762/bjoc.20.94 Abstract An efficient method for the synthesis of isoxazolo[4,5-b]pyridines has been developed on

Novel analogues of a nonnucleoside SARS-CoV-2 RdRp inhibitor as potential antivirotics

• Luca Julianna Tóth,
• Kateřina Krejčová,
• Milan Dejmek,
• Eva Žilecká,
• Blanka Klepetářová,
• Lenka Poštová Slavětínská,
• Evžen Bouřa and
• Radim Nencka

Beilstein J. Org. Chem. 2024, 20, 1029–1036, doi:10.3762/bjoc.20.91

• Luca Julianna Toth Katerina Krejcova Milan Dejmek Eva Zilecka Blanka Klepetarova Lenka Postova Slavetinska Evzen Boura Radim Nencka Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 2030/8, 128 43 Prague, Czech Republic Institute of Organic Chemistry and Biochemistry

• : Experimental procedures, spectra and X-ray data. Acknowledgements We thank Lucie Bednárová from the Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences for the help with the analysis of compound 13. Funding The work was supported by the National Institute of Virology and

Auxiliary strategy for the general and practical synthesis of diaryliodonium(III) salts with diverse organocarboxylate counterions

• Naoki Miyamoto,
• Daichi Koseki,
• Kohei Sumida,
• Elghareeb E. Elboray,
• Naoko Takenaga,
• Ravi Kumar and
• Toshifumi Dohi

Beilstein J. Org. Chem. 2024, 20, 1020–1028, doi:10.3762/bjoc.20.90

• in organic chemistry and other scientific fields. The potential of diaryliodonium(III) carboxylates obtained in this study (i.e., Scheme 6B,C) and the related amino acid derivatives [46][47][48][49] as new arylating reagents will be further explored by conducting reactions with various nucleophiles