Synthesis of photo- and ionochromic N-acylated 2-(aminomethylene)benzo[b]thiophene-3(2Н)-ones with a terminal phenanthroline group

• Vladimir P. Rybalkin,
• Sofiya Yu. Zmeeva,
• Lidiya L. Popova,
• Irina V. Dubonosova,
• Olga Yu. Karlutova,
• Oleg P. Demidov,
• Alexander D. Dubonosov and
• Vladimir A. Bren

Beilstein J. Org. Chem. 2024, 20, 552–560, doi:10.3762/bjoc.20.47

• Physical and Organic Chemistry, Southern Federal University, Rostov-on-Don 344090, Russian Federation North Caucasus Federal University, Stavropol 355009, Russian Federation 10.3762/bjoc.20.47 Abstract A series of novel photo- and ionochromic N-acylated 2-(aminomethylene)benzo[b]thiophene-3(2Н)-ones with

Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

• Jens Frackenpohl,
• David M. Barber,
• Guido Bojack,
• Birgit Bollenbach-Wahl,
• Ralf Braun,
• Rahel Getachew,
• Sabine Hohmann,
• Kwang-Yoon Ko,
• Karoline Kurowski,
• Bernd Laber,
• Rebecca L. Mattison,
• Thomas Müller,
• Anna M. Reingruber,
• Dirk Schmutzler and
• Andrea Svejda

Beilstein J. Org. Chem. 2024, 20, 540–551, doi:10.3762/bjoc.20.46

• , 2.28 mmol, 0.04 equiv), and the mixture was stirred at 80 °C for 3 h. Thereafter, the reaction mixture was cooled to room temperature, diluted with water, and extracted thoroughly with ethyl acetate. The combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated under

• was added, followed by thorough extraction. The combined organic layer was dried over magnesium sulfate, filtered, and dried under reduced pressure. The remaining residue was purified via column chromatography (gradient ethyl acetate/hexane) to afford 6-bromo-5-(2-fluorophenyl)[1,3]thiazolo[4,5-b

• acetonitrile, formic acid was added, and the reaction mixture was stirred at room temperature for 2 h. The phases were separated via phase separator, and the organic layer was concentrated under reduced pressure. The remaining crude product was purified via column chromatography (gradient ethyl acetate/hexane

Switchable molecular tweezers: design and applications

• Pablo Msellem,
• Maksym Dekthiarenko,
• Nihal Hadj Seyd and
• Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

• solution. This concept was further developed with a bis-acridinium cyclophane [31] as a multiresponsive receptor for selective phase transfer. In organic media, this macrocyclic receptor presented an affinity for polyaromatic guests with strong selectivity for perylene. A reversible guest release was

Ligand effects, solvent cooperation, and large kinetic solvent deuterium isotope effects in gold(I)-catalyzed intramolecular alkene hydroamination

• Ruichen Lan,
• Brock Yager,
• Yoonsun Jee,
• Cynthia S. Day and
• Amanda C. Jones

Beilstein J. Org. Chem. 2024, 20, 479–496, doi:10.3762/bjoc.20.43

• and organic molecules [6]. Our results here are consistent, but the dynamics of mixed solvent systems are complex – water in DCM enhances rates, while water in MeOH nearly shuts them down. We presume these are consistent with the solubility effects proposed by Michon. In DCM, protic co-solvents were

Pseudallenes A and B, new sulfur-containing ovalicin sesquiterpenoid derivatives with antimicrobial activity from the deep-sea cold seep sediment-derived fungus Pseudallescheria boydii CS-793

• Zhen Ying,
• Xiao-Ming Li,
• Sui-Qun Yang,
• Hong-Lei Li,
• Xin Li,
• Bin-Gui Wang and
• Ling-Hong Meng

Beilstein J. Org. Chem. 2024, 20, 470–478, doi:10.3762/bjoc.20.42

• Discussion For chemical investigation, the solvent EtOAc was used to extract the fermentation culture of the fungus P. boydii CS-793 to afford an organic extract. Isolation and purification of the crude extract with a combination of column chromatography (CC) by Lobar LiChroprep RP-18, silica gel, Sephadex

• concentrated under reduced pressure to give 123.6 g of an organic extract. The EtOAc extract was subjected to Si gel VLC (vacuum liquid chromatography) and fractionated using solvent mixtures of increasing polarity consisting of petroleum ether (PE) and EtOAc 20:1 to 1:1 and finally with CH2Cl2/MeOH 20:1 to 1

Synthesis of 2,2-difluoro-1,3-diketone and 2,2-difluoro-1,3-ketoester derivatives using fluorine gas

• Alexander S. Hampton,
• David R. W. Hodgson,
• Graham McDougald,
• Linhua Wang and
• Graham Sandford

Beilstein J. Org. Chem. 2024, 20, 460–469, doi:10.3762/bjoc.20.41

• difluoromethylene units. To meet the demands of synthetic chemists within the life science discovery and manufacturing arenas, many fluorination methods have been developed over the years to introduce difluoromethylene groups into organic systems. Approaches using nucleophilic fluorination include halogen exchange

• difluoromethylphenyl sulfoxide offer the possibility of transferring difluoromethylene groups directly into organic systems [19][20][21][22][23][24][25] and there is now a very extensive literature on carbon–carbon bond-forming reactions using these and other difluoromethylated building blocks [3][26][27][28][29][30

• ) gave only relatively low conversions to 2a and 3a. Other organic nitrogen bases were tested, and we found that quinuclidine (entries 8 and 9, Table 1) gave high conversion to difluorinated product 3a, with very little monofluorinated product 2a being observed. Suspensions of caesium carbonate or sodium

(E,Z)-1,1,1,4,4,4-Hexafluorobut-2-enes: hydrofluoroolefins halogenation/dehydrohalogenation cascade to reach new fluorinated allene

• Nataliia V. Kirij,
• Andrey A. Filatov,
• Yurii L. Yagupolskii,
• Sheng Peng and
• Lee Sprague

Beilstein J. Org. Chem. 2024, 20, 452–459, doi:10.3762/bjoc.20.40

• Nataliia V. Kirij Andrey A. Filatov Yurii L. Yagupolskii Sheng Peng Lee Sprague Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Academician Kukhar Str., 5, Kyiv-94, 02660, Ukraine The Chemours Company, Chemours Discovery Hub, Newark, DE 19713, United States 10.3762/bjoc

• on an industrial scale [2]. These hydrofluoroolefins belong to the newest 4th generation of fluorocarbon refrigerants and are promising compounds and starting materials. Due to this, interest in the use of (E)- and (Z)-butenes 1a,b as synthons in various organic transformations has recently grown

• . The reaction mixture gave a complex mixture, in which (E)-butene 3a was identified as a major component. Product 3a was removed from bulk diglyme in vacuum and after subsequent distillation it was isolated with a yield of 23%. As the isolation of the 2-dehydrobromination products from organic bases

Enhanced host–guest interaction between [10]cycloparaphenylene ([10]CPP) and [5]CPP by cationic charges

• Eiichi Kayahara,
• Yoshiyuki Mizuhata and
• Shigeru Yamago

Beilstein J. Org. Chem. 2024, 20, 436–444, doi:10.3762/bjoc.20.38

• chemistry; Introduction Since the first bottom-up organic synthesis of cycloparaphenylenes (CPPs) [1][2][3][4][5][6][7], which are the carbon nanorings with the shortest possible structural constituent of armchair carbon nanotubes (CNTs), a new science of cyclic nanocarbons has emerged through synthesizing

Mono or double Pd-catalyzed C–H bond functionalization for the annulative π-extension of 1,8-dibromonaphthalene: a one pot access to fluoranthene derivatives

• Nahed Ketata,
• Linhao Liu,
• Ridha Ben Salem and
• Henri Doucet

Beilstein J. Org. Chem. 2024, 20, 427–435, doi:10.3762/bjoc.20.37

• Nahed Ketata Linhao Liu Ridha Ben Salem Henri Doucet University of Rennes, CNRS, ISCR-UMR 6226, F-35000 Rennes, France Organic chemistry laboratory, LR17ES08, Department of Chemistry, Faculty of Sciences, University of Sfax, B.P. 1171, 3038, Sfax, Tunisia 10.3762/bjoc.20.37 Abstract The Pd

• these reactions require high catalyst or base loadings, and offer a very limited scope regarding the use of reagents featuring functional groups useful in organic synthesis. Consequently, the discovery of simpler and more efficient synthetic procedures for the preparation of fluoranthene derivatives

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

• Periklis X. Kolagkis Eirini M. Galathri Christoforos G. Kokotos Laboratory of Organic Chemistry, Department of Organic Chemistry, National and Kapodistrian University of Athens, Athens, 15771, Greece 10.3762/bjoc.20.36 Abstract The synthesis of indoles and their derivatives, more specifically bis

• (indolyl)methanes (BIMs), has been an area of great interest in organic chemistry, since these compounds exhibit a range of interesting biological and pharmacological properties. BIMs are naturally found in cruciferous vegetables and have been shown to be effective antifungal, antibacterial, anti

• synthetic pathways in organic chemistry [32][33][34]. Common organic syntheses require the use of harmful chemicals, such as toxic solvents, hazardous reagents, catalysts and reaction conditions, which contribute to environmental pollution and soil degradation [35][36]. Wanting to enhance the sustainability

Mechanisms for radical reactions initiating from N-hydroxyphthalimide esters

• Carlos R. Azpilcueta-Nicolas and
• Jean-Philip Lumb

Beilstein J. Org. Chem. 2024, 20, 346–378, doi:10.3762/bjoc.20.35

• chemistry is well documented [1][2]. Traditional approaches for radical generation relied on hazardous reagents and harsh conditions, resulting in low reaction efficiency and undesired byproduct formation [3][4][5][6]. As a consequence, the utility of radicals in organic synthesis remained limited for many

• , leading to their strategic incorporation as "synthons" in modern organic chemistry, with complementary reactivity to more common polar reaction manifolds [12][13][14][15]. The utility of radicals has also been expanded through the recent development of transformations involving radical-polar crossover

• esters for the construction of quaternary carbons via conjugate addition of 3° radicals [39][40]. In general, this transformation operates under a reductive quenching photocatalytic cycle, requiring a stoichiometric reductant (Scheme 4A). Both TM complexes, and organic dyes such as eosin Y [41][42][43

Facile approach to N,O,S-heteropentacycles via condensation of sterically crowded 3H-phenoxazin-3-one with ortho-substituted anilines

• Eugeny Ivakhnenko,
• Vasily Malay,
• Pavel Knyazev,
• Nikita Merezhko,
• Nadezhda Makarova,
• Oleg Demidov,
• Gennady Borodkin,
• Andrey Starikov and
• Vladimir Minkin

Beilstein J. Org. Chem. 2024, 20, 336–345, doi:10.3762/bjoc.20.34

• Eugeny Ivakhnenko Vasily Malay Pavel Knyazev Nikita Merezhko Nadezhda Makarova Oleg Demidov Gennady Borodkin Andrey Starikov Vladimir Minkin Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachki St., 344090, Rostov-on-Don, Russian Federation North Caucasus Federal

• probes, organic light-emitting diodes, and organic solar cells [2][7][8][9]. The principal way for the preparation of these heterocycles involves the coupling of 3H-phenoxazin-3-ones with variously functionalized aromatic amines. This is followed by the cyclization of the initially formed adducts [10][11

• amines, the direction of which is controlled by the large positive charge at the C(2) center of the p-quinone imine moiety of the heterocycle. With this in mind, we turned our attention to solid-state organic reactions. Numerous examples of nucleophilic substitutions at carbon centers are discussed in

Spatial arrangements of cyclodextrin host–guest complexes in solution studied by ¹³C NMR and molecular modelling

• Konstantin Lebedinskiy,
• Ivan Barvík,
• Zdeněk Tošner,
• Ivana Císařová,
• Jindřich Jindřich and
• Radim Hrdina

Beilstein J. Org. Chem. 2024, 20, 331–335, doi:10.3762/bjoc.20.33

• Konstantin Lebedinskiy Ivan Barvik Zdenek Tosner Ivana Cisarova Jindrich Jindrich Radim Hrdina Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 8, 128 43 Praha, Czech Republic Institute of Physics, Faculty of Mathematics and Physics, Charles University, Ke Karlovu

• crystallization of host–guest complexes and their crystallographic analysis. Keywords: anisotropy; 13C NMR; cyclodextrin; host–guest complexes; Introduction Complexation of organic and inorganic compounds with α-, β-, or γ-cyclodextrins and their derivatives [1] is an established tool used in medicine for drug

Discovery of unguisin J, a new cyclic peptide from Aspergillus heteromorphus CBS 117.55, and phylogeny-based bioinformatic analysis of UngA NRPS domains

• Sharmila Neupane,
• Marcelo Rodrigues de Amorim and
• Elizabeth Skellam

Beilstein J. Org. Chem. 2024, 20, 321–330, doi:10.3762/bjoc.20.32

• . heteromorphus CBS 117.55 on rice solid medium yielded an organic-soluble extract, which was subjected to fractionation using preparative HPLC-PDA-ELSD and purification by semipreparative HPLC-PDA; this led to the isolation of a new cyclic peptide 1, along with unguisin B (2, Figure 2). The structure of the new

• substrates. Experimental General experimental procedures A. heteromorphus CBS 117.55 (also known as A. heteromorphus NRRL 4747) was purchased from the ARS Culture Collection. Rice solid medium was purchased from RiceSelect Organic Texmati. All solvents used for conducting LC analysis were purchased from

• . The CH3CN fraction was evaporated, yielding 0.601 g of soluble-organic extract. Fractionation and isolation of unguisins J and B The soluble-organic extract was fractionated by preparative HPLC-PDA using Kinetex RP18 column (250 mm × 30 mm i.d., 5 μm) and UV detector at λmax = 254 nm. The mobile phase

Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

• Aissam Okba,
• Pablo Simón Marqués,
• Kyohei Matsuo,
• Naoki Aratani,
• Hiroko Yamada,
• Gwénaël Rapenne and
• Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

• synthesized via in-solution organic chemistry, for their improved processing, as well as for their electronic investigation both at the material and single-molecule scales. This method relies on the synthesis and processing of soluble and stable direct precursors of the target π-CPCs, followed by their final

• -conjugated polycyclic compounds appeared as particularly valuable in this field. Indeed, many of them demonstrated excellent performances as active components of electronic devices such as organic field effect transistors (OFETs), organic photovoltaic cells (OPVs) and organic light-emitting diodes (OLEDs

• ). This has prompted an ever-increasing number of research groups to design new synthetic routes towards π-CPCs, aiming at i) new organic structures for improved performances, ii) higher synthetic efficiency and modularity, and iii) better processability of target compounds to build opto-electronic

Synthesis of spiropyridazine-benzosultams by the [4 + 2] annulation reaction of 3-substituted benzoisothiazole 1,1-dioxides with 1,2-diaza-1,3-dienes

• Wenqing Hao,
• Long Wang,
• Jinlei Zhang,
• Dawei Teng and
• Guorui Cao

Beilstein J. Org. Chem. 2024, 20, 280–286, doi:10.3762/bjoc.20.29

• investigated the performance of other organic and inorganic bases, but they did not improve the yield (Table 1, entries 8–12). The structure of spiropyridazine-benzosultam 3aa was determined by 1H NMR, 13C NMR, HRMS analysis and single-crystal X-ray crystallography [33]. Further experiments conducted with

Nucleophilic functionalization of thianthrenium salts under basic conditions

• Xinting Fan,
• Duo Zhang,
• Xiangchuan Xiu,
• Bin Xu,
• Yu Yuan,
• Feng Chen and
• Pan Gao

Beilstein J. Org. Chem. 2024, 20, 257–263, doi:10.3762/bjoc.20.26

• ][5][6][7][8][9][10] have been extensively utilized as readily accessible synthetic building blocks in organic synthesis, particularly in the ipso-functionalization of C–S bonds. Of the sulfonium salts, organothianthrenium salts exhibit distinct structural properties and reactivities, thereby offering

• further potential in organic synthesis. Despite establishing a few preliminary methods for preparing organothianthrenium salts, their application potential is historically thwarted by harsh synthetic conditions and the poor durability of the resulting products [7]. Recently, Ritter and co-workers have

Catalytic multi-step domino and one-pot reactions

• Svetlana B. Tsogoeva

Beilstein J. Org. Chem. 2024, 20, 254–256, doi:10.3762/bjoc.20.25

• Svetlana B. Tsogoeva Department of Chemistry and Pharmacy, Organic Chemistry Chair I and Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Nikolaus Fiebiger-Straße 10, 91058 Erlangen, Germany 10.3762/bjoc.20.25 Keywords: domino reactions

• atom efficiency, step and pot economies, decreased number of purification steps, or protecting-group-free synthesis. Multi-step domino [1][2] and one-pot [3] reactions represent a new powerful toolbox in organic synthesis to install molecular complexity economically and sustainably, starting from

• steps, which is superior to conventional organic synthesis. The Thematic Issue “Catalytic multi-step domino and one-pot reactions” in the Beilstein Journal of Organic Chemistry, which I had the pleasure to edit, covers the recent strategies of domino reactions and one-pot syntheses and presents the

Substitution reactions in the acenaphthene analog of quino[7,8-h]quinoline and an unusual synthesis of the corresponding acenaphthylenes by tele-elimination

• Ekaterina V. Kolupaeva,
• Narek A. Dzhangiryan,
• Alexander F. Pozharskii,
• Oleg P. Demidov and
• Valery A. Ozeryanskii

Beilstein J. Org. Chem. 2024, 20, 243–253, doi:10.3762/bjoc.20.24

• Ekaterina V. Kolupaeva Narek A. Dzhangiryan Alexander F. Pozharskii Oleg P. Demidov Valery A. Ozeryanskii Department of Organic Chemistry, Southern Federal University, Zorge str. 7, 344090 Rostov-on-Don, Russian Federation Department of Chemistry and Pharmacy, North Caucasus Federal University

• of the corresponding monoprotonated forms are given). Meanwhile, the very synthesis of polycondensed quinoline bases with a certain arrangement of nitrogen atoms is often a challenge for a synthetic scientist [9][10]. This greatly limits the possible use of such polynuclear azaarenes in organic

• 1:1 (Scheme 2). Complex 9 is insoluble in most organic solvents, but it turned out to be unstable in DMSO-d6 solution, as evidenced by monitoring its 1Н NMR spectra (Supporting Information File 1, Figure S1). Figure S1a shows the spectrum of the starting quinoline 5, Figure S1b represents complex 9

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

• and unsymmetrical N,N'-substituted alkyl- and arylindigos with tunable thermal half-lives (follow-up mechanistic studies in 2022) 2018: first report on photochromic monoarylated indigos Synthesis of indigo derivatives Indigo (Ind) is one of the oldest organic molecules, which has been used as a dye

• water. Thus, the thermal Z–E relaxation of 20b could be significantly accelerated (ca. 300 times) by addition of water to organic solvent because of specific interactions between the NH groups and water molecules. Photochromic N-aryl-N'-alkylindigos In 2017 Hecht, Jacquemin, and co-workers prepared

• tinctoria plant. Like indirubins, the isoindigo derivatives were initially studied as potential therapeutics with pronounced antitumor activity [74]. More recently, advantageous charateristics of isoindigos for the applications in organic photovoltaics (OPV) [75] and optoelectronics [76] were revealed. The

Copper-catalyzed multicomponent reaction of β-trifluoromethyl β-diazo esters enabling the synthesis of β-trifluoromethyl N,N-diacyl-β-amino esters

• Youlong Du,
• Haibo Mei,
• Ata Makarem,
• Ramin Javahershenas,
• Vadim A. Soloshonok and
• Jianlin Han

Beilstein J. Org. Chem. 2024, 20, 212–219, doi:10.3762/bjoc.20.21

• Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany Department of Organic Chemistry, Faculty of Chemistry, Urmia University, Urmia, Iran Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country (UPV/EHU), Paseo Manuel Lardizábal 3, San Sebastián, 20018, Spain

• esters; Introduction The insertion of fluorine-containing components frequently confers desirable physical and biological properties to organic molecules, and the development of fluorine-containing drugs is an important field of research [1][2][3][4][5][6][7][8][9]. It is estimated that 30% of drugs and

• organic synthesis, as they can be used as diazo intermediates or carbene precursors for the rapid construction of complex molecules along with the introduction of fluoroalkyl groups [14][15][16]. Although the reaction of trifluorodiazoethane [17][18][19][20][21][22][23][24][25][26][27] as well as α-diazo

Chiral phosphoric acid-catalyzed transfer hydrogenation of 3,3-difluoro-3H-indoles

• Yumei Wang,
• Guangzhu Wang,
• Yanping Zhu and
• Kaiwu Dong

Beilstein J. Org. Chem. 2024, 20, 205–211, doi:10.3762/bjoc.20.20

• excellent yield and enantioselectivity. Keywords: asymmetric organocatalysis; chiral Brønsted acid; 3,3-difluoroindoline; Hantzsch ester; transfer hydrogenation; Introduction The introduction of fluoro atoms into organic molecules can alter their lipophilicity, solubility, metabolic stability, and

• great attention in organic synthesis. Various methods [9], including reductive hydrogenation [10][11], kinetic resolution [12][13][14], functionalization of indole [15], and de novo construction of chiral 2-substituted indolines, have been developed [16][17][18][19][20]. In recent years, the metal

Comparison of glycosyl donors: a supramer approach

• Anna V. Orlova,
• Nelly N. Malysheva,
• Maria V. Panova,
• Nikita M. Podvalnyy,
• Michael G. Medvedev and
• Leonid O. Kononov

Beilstein J. Org. Chem. 2024, 20, 181–192, doi:10.3762/bjoc.20.18

• Anna V. Orlova Nelly N. Malysheva Maria V. Panova Nikita M. Podvalnyy Michael G. Medvedev Leonid O. Kononov Laboratory of Glycochemistry, N.D. Zelinsky Institute of Organic Chemistry, Moscow, Russian Federation Theoretical Chemistry Group, N.D. Zelinsky Institute of Organic Chemistry, Moscow

• NaHSO4 (100 mL), and saturated aqueous NaHCO3 (100 mL). An additional extraction with CH2Cl2 (2 × 50 mL) was performed from each aqueous layer. The combined organic extracts were filtered through a cotton wool plug, concentrated under reduced pressure, and dried in vacuo as described previously [36]. The

• . The reaction mixture was kept at room temperature overnight, then quenched by addition of methanol (3 mL), and concentrated under reduced pressure. The residue was co-concentrated with toluene (3 mL), dissolved in CH2Cl2 (40 mL), washed with water (40 mL), the organic layer was filtered through a

Synthesis of the 3’-O-sulfated TF antigen with a TEG-N₃ linker for glycodendrimersomes preparation to study lectin binding

• Mark Reihill,
• Hanyue Ma,
• Dennis Bengtsson and
• Stefan Oscarson

Beilstein J. Org. Chem. 2024, 20, 173–180, doi:10.3762/bjoc.20.17

• Celite® and concentrated in vacuo. The resulting residue was taken up in EtOAc (700 mL) and washed with 10% aq Na2S2O3 (700 mL), water (700 mL) and brine (700 mL). The organic phase was then dried over MgSO4, filtered and reduced to dryness. Flash chromatography on silica gel (toluene→toluene/EtOAc, 3:2

Tandem Hock and Friedel–Crafts reactions allowing an expedient synthesis of a cyclolignan-type scaffold

• Viktoria A. Ikonnikova,
• Cristina Cheibas,
• Oscar Gayraud,
• Alexandra E. Bosnidou,
• Nicolas Casaretto,
• Gilles Frison and
• Bastien Nay

Beilstein J. Org. Chem. 2024, 20, 162–169, doi:10.3762/bjoc.20.15

• –Crafts reactions, rather than an oxocarbenium. Keywords: 1-aryltetralines; Friedel–Crafts reaction; Hock rearrangement; oxidative cleavage; tandem reactions; Introduction The Hock cleavage [1] consists in the acid-catalyzed rearrangement of organic hydroperoxides, leading to the oxidative cleavage of a