Unprecedented visible light-initiated topochemical [2 + 2] cycloaddition in a functionalized bimane dye

• Metodej Dvoracek,
• Brendan Twamley,
• Mathias O. Senge and
• Mikhail A. Filatov

Beilstein J. Org. Chem. 2025, 21, 500–509, doi:10.3762/bjoc.21.37

• with the Schmidt criteria for topochemical cycloaddition. Additionally, two other bimane derivatives with different substitution patterns were synthesized and investigated. Our findings suggest that functionalizing bimanes to redshift their absorption maxima into the visible-light spectrum provides a

Synthesis of N-acetyl diazocine derivatives via cross-coupling reaction

• Thomas Brandt,
• Pascal Lentes,
• Jeremy Rudtke,
• Michael Hösgen,
• Christian Näther and
• Rainer Herges

Beilstein J. Org. Chem. 2025, 21, 490–499, doi:10.3762/bjoc.21.36

• switching efficiency in aqueous solutions. In order to investigate the chemistry of this promising photoswitch and to unlock further applications, we now investigate strategies for the synthesis of derivatives, which are based on cross-coupling reactions. Fourteen vinyl-, aryl-, cyano-, and amino

• -substituted diazocines were prepared via Stille, Suzuki, and Buchwald–Hartwig reactions. X-ray structures are presented for derivatives 1, 2 and 7. Keywords: cross-coupling; diazocine; N-acetyl diazocine; photoisomerization; photoswitch; thermal relaxation; Introduction Diazocines are frequently used

• diazocine 23 in yields of 61% from bromide 2 and 81% from iodide 3 (Scheme 3). Nitriles are a good starting point for further functional group interconversions [39]. Photochemical characterization With these new N-acetyl diazocine derivatives at hand we turned towards the photochemical characterization, in

Synthesis of electrophile-tethered preQ₁ analogs for covalent attachment to preQ₁ RNA

• Laurin Flemmich and
• Ronald Micura

Beilstein J. Org. Chem. 2025, 21, 483–489, doi:10.3762/bjoc.21.35

• transcription or translation of the mRNA and results in altered transcript and/or protein levels [5]. In recent years, there has been a growing interest in the modification of preQ1. preQ1 derivatives, preQ1 analogs and mimics of preQ1 have greatly expanded our understanding of preQ1-binding biomolecules, such

• vitro and in living cells using rationally designed electrophile-tethered derivatives of preQ1 (1) and its Watson–Crick diamino-faced counterpart DPQ1 (2, Scheme 1A). These ligands (compound classes 3 and 4, Scheme 1A) were tailored to target a conserved guanine nucleobase within a natural preQ1-binding

• derivatives have been reported [22][23][24][25][26]. Among these reports, various silylation and protection strategies have been employed to address the poor solubility of preQ1 (and analogs) in organic solvents [9][22][23][25][26][27][28][29]. Herein, we report an optimized three-step protocol, free of

Organocatalytic kinetic resolution of 1,5-dicarbonyl compounds through a retro-Michael reaction

• James Guevara-Pulido,
• Fernando González-Pérez,
• José M. Andrés and
• Rafael Pedrosa

Beilstein J. Org. Chem. 2025, 21, 473–482, doi:10.3762/bjoc.21.34

• conditions tested. Similarly, the resolution of nitro aldehydes 16 and 17, prepared by Michael addition of nitromethane to α,β-unsaturated aldehydes (entries 16 and 17, Table 5), was tested, and the same results were obtained as in the cases of the malonate derivatives. These results indicate that dicarbonyl

• compounds are better leaving groups than diesters or nitro derivatives in this type of transformation. Another possible explanation is that Michael adducts other than 1,5-dicarbonyl compounds require more robust bases to shift the equilibrium toward the retro-Michael product. It is essential to highlight

New tandem Ugi/intramolecular Diels–Alder reaction based on vinylfuran and 1,3-butadienylfuran derivatives

• Yuriy I. Horak,
• Roman Z. Lytvyn,
• Andrii R. Vakhula,
• Yuriy V. Homza,
• Nazariy T. Pokhodylo and
• Mykola D. Obushak

Beilstein J. Org. Chem. 2025, 21, 444–450, doi:10.3762/bjoc.21.31

• reaction and Diels–Alder [4 + 2] cycloaddition based on vinylfuran and 1,3-butadienylfuran derivatives was designed and studied. It was found that in the case of 3-(furan-2-yl)acrylaldehyde, a one-pot Ugi reaction and intramolecular Diels–Alder vinylarene (IMDAV) reaction leads to the formation of the

• insufficiently studied furo[2,3-f]isoindole derivatives. Ugi adducts formed from (E)-3-(furan-2-yl)acrylaldehyde, maleic acid monoanilide, isonitrile, and an amine spontaneously underwent the IMDAV reaction with a high level of stereoselectivity, leading to single pairs of enantiomers of 4,4a,5,6,7,7a-hexahydro

• [11][12][13]. Advancements in one-pot syntheses, like combining the Ugi reaction with other methods [14][15][16][17][18], for example, the Huisgen cycloaddition, have led to the creation of unique [1,2,3]triazolo[1,5-a]pyrazine derivatives [19]. Tandem reactions are particularly valued for their atom

Unraveling aromaticity: the dual worlds of pyrazole, pyrazoline, and 3D carborane

• Zahra Noori,
• Miquel Solà,
• Clara Viñas,
• Francesc Teixidor and
• Jordi Poater

Beilstein J. Org. Chem. 2025, 21, 412–420, doi:10.3762/bjoc.21.29

• , exceptional thermal and chemical stability, and robust synthetic versatility [16][17] – make carborane derivatives essential components in various fields. These include pharmaceuticals [18][19][20][21][22], boron neutron capture therapy (BNCT) [23][24][25][26], organometallic ligands [27], and functional

Identification and removal of a cryptic impurity in pomalidomide-PEG based PROTAC

• Bingnan Wang,
• Yong Lu and
• Chuo Chen

Beilstein J. Org. Chem. 2025, 21, 407–411, doi:10.3762/bjoc.21.28

• sulfonate to the byproduct by reacting it with taurine allows for easy decontamination. This method may facilitate the purification of other similar reactions and improve the quality of related pomalidomide derivatives. The structures of veliparib and iVeliparib-AP6. Identification of the cryptic impurity

• silica gel column chromatography. The LUMO and electrostatic charges of thalidomide and its derivatives by DFT calculation at the ωB97X-D/6-311+G** level. The synthetic route for iVeliparib-AP6. The conversion of byproduct 6 to 10 to facilitate its removal. Effects of the length and functionalization of

The effect of neighbouring group participation and possible long range remote group participation in O-glycosylation

• Rituparna Das and
• Balaram Mukhopadhyay

Beilstein J. Org. Chem. 2025, 21, 369–406, doi:10.3762/bjoc.21.27

• successfully substituted the acetyl group with the benzoyl group to primarily obtain 1,2-trans glycosides [83][84][85]. Ishida et al. implemented benzoyl protection for the synthesis of 1,2-trans glycosides for the iterative synthesis of oligo-α-rhamnoside derivatives [86]. Both acetyl and benzoyl groups

• glycosylation reactions making them solvent-free and being more environment friendly without compromising on the stereoselectivity. Thus, the acetyl and benzoyl group and similar derivatives are the most widely used protecting groups to obtain 1,2-trans glycosides in oligosaccharide syntheses. Ester groups in

• hydrogenation step to yield the product 38 [107]. Compound 37 shows all-1,2-trans glycosidic bonds due to the installed pivaloyl group in the C-2 position. This cyanopivaloyl group is also widely used in solid-phase automated oligosaccharide synthesis [107] for the synthesis of oligorhamnoside derivatives. Thus

Synthesis, structure, ionochromic and cytotoxic properties of new 2-(indolin-2-yl)-1,3-tropolones

• Yurii A. Sayapin,
• Eugeny A. Gusakov,
• Inna O. Tupaeva,
• Alexander D. Dubonosov,
• Igor V. Dorogan,
• Valery V. Tkachev,
• Anna S. Goncharova,
• Gennady V. Shilov,
• Natalia S. Kuznetsova,
• Svetlana Y. Filippova,
• Tatyana A. Krasnikova,
• Yanis A. Boumber,
• Alexey Y. Maksimov,
• Sergey M. Aldoshin and
• Vladimir I. Minkin

Beilstein J. Org. Chem. 2025, 21, 358–368, doi:10.3762/bjoc.21.26

• Comprehensive Cancer Center at University of Alabama at Birmingham, Department of Medicine, Section of Hematology/Oncology, Heersink School of Medicine, Birmingham, AL 35233, USA 10.3762/bjoc.21.26 Abstract The acid-catalyzed reaction of benzo[e(g)] derivatives of 2,3,3-trimethylindolenines with o-chloranil

• antibacterial [4] and cytotoxic activity [6][7]. Existing approaches to the synthesis of 1,3-tropolone derivatives have a number of drawbacks, namely, limited synthesis methodology and low yields of the target compounds [8][9][10][11][12][13][14][15]. Over the past decade, only a few reports have been published

• [16][17]. Indole derivatives, including those with conjugated aromatic and alicyclic rings, are of considerable interest because of their diverse biological activities (antibacterial, antimicrobial, anticancer, antidiabetic, etc.) [18][19][20][21][22]. For this reason, the synthetic goal of this work

Synthesis, characterization, antimicrobial, cytotoxic and carbonic anhydrase inhibition activities of multifunctional pyrazolo-1,2-benzothiazine acetamides

• Ayesha Saeed,
• Shahana Ehsan,
• Muhammad Zia-ur-Rehman,
• Erin M. Marshall,
• Sandra Loesgen,
• Abdus Saleem,
• Simone Giovannuzzi and
• Claudiu T. Supuran

Beilstein J. Org. Chem. 2025, 21, 348–357, doi:10.3762/bjoc.21.25

• are synthesized by incorporation of benzothiazine, pyrazole, and amide moieties in a new scaffold to create multifunctional derivatives of pyrazolo-1,2-benzothiazine. The presented compounds have been synthesized and analyzed using spectroscopic and spectrometric techniques including FTIR, HRMS, 1H

• cell line HCT-116 (ATCC CCL-247) revealed that only compound 7l inhibited cell viability, while the rest of the compounds including 7b and 7h showed no significant decrease in mammalian cell viability. Results of human carbonic anhydrase (hCA) inhibition assays discovered that monoalkylated derivatives

• biologically active useful candidates. NSAIDs (non-steroidal anti-inflammatory drugs) currently approved like piroxicam [12], meloxicam [13], and other derivatives of these two are well known for their activities [5]. 1,2-Benzothiazines are highly bioactive moieties and have been explored as antibacterial [14

Antibiofilm and cytotoxic metabolites from the entomopathogenic fungus Samsoniella aurantia

• Rita Toshe,
• Syeda J. Khalid,
• Blondelle Matio Kemkuignou,
• Esteban Charria-Girón,
• Paul Eckhardt,
• Birthe Sandargo,
• Kunlapat Nuchthien,
• J. Jennifer Luangsa-ard,
• Till Opatz,
• Hedda Schrey,
• Sherif S. Ebada and
• Marc Stadler

Beilstein J. Org. Chem. 2025, 21, 327–339, doi:10.3762/bjoc.21.23

• and five 2-pyridone derivatives that revealed potential antibiofilm activity against Staphylococcus aureus biofilms [7]. These results encouraged us to explore a member of the Cordycipitaceae, in the genus Samsoniella that was segregated from Akanthomyces based on morphological and molecular evidence

• δC 34.2 (C-12) and 29.7 (C-13), respectively. The HMBC correlations (Figure 3) indicated that the side chain in 1 ends as –C(CH3)=CH-CH(CH3)-CH2-CH3 resembling those from farinosones A/B [8] and tenellin derivatives [10][11]. The relative configuration of 1 was elucidated based on its ROESY spectrum

• groups ascribed to H3-14 and H3-15 together with a diastereotopic methylene group at δH 1.25/1.36 (H2-13) confirming the depicted end of the aliphatic sidechain as –C(CH3)=CH-CH(CH3)-CH2-CH3 similar to that in farinosones A/B [8] and tenellin derivatives [10][11]. To establish the absolute configuration

Red light excitation: illuminating photocatalysis in a new spectrum

• Lucas Fortier,
• Corentin Lefebvre and
• Norbert Hoffmann

Beilstein J. Org. Chem. 2025, 21, 296–326, doi:10.3762/bjoc.21.22

• photocatalysts, such as helical carbenium ions and advanced nitrobenzofuran derivatives for applications in phototherapy and controlled drug release, underscoring the potential of red-light photocatalysis in biomedicine. Review Red-light photocatalysis with metal-based complexes Metal-based complexes naturally

• properties of metal complexes. Phthalocyanins, porphyrins, and their derivatives exemplify this, as their rigid macrocyclic structures enable strong absorption in the visible to NIR regions, making them appealing for photoredox catalysis applications. For instance, ruthenium phthalocyanin complexes have

• emerged as potent catalysts for red-light-mediated photoreactions. Furuyama et al. demonstrated that a ruthenium phthalocyanin complex could catalyze trifluoromethylation reactions of styrene derivatives 18 with either CF3SO2Cl or Umemoto’s reagent 19 under red-light irradiation without the need for

Molecular diversity of the reactions of MBH carbonates of isatins and various nucleophiles

• Zi-Ying Xiao,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2025, 21, 286–295, doi:10.3762/bjoc.21.21

• . Diverse functionalized 3-substituted oxindole derivatives were successfully prepared in satisfactory yields and with high diastereoselectivity. In addition, the base-promoted dimerization of MBH carbonates of isatin afforded the ethylene-bridged bis(3-methylene)oxindole derivatives with nearly 4:1

• biologically important 3-substituted and spirooxindole derivatives [5][6][7]. The unique molecular architecture and remarkable pharmacological activities have made spirooxindole one of the hottest synthetic targets with fruitful chemical and steric selectivity [8][9][10][11][12][13][14][15]. In recent years

• ]. In the presence of a Lewis base, MBH carbonates of isatins can be easily converted to activated allylic ylides, which in turn can undergo allylic substitution and annulation reactions to give diverse 3-substituted and spirooxindole derivatives [36][37][38][39][40][41]. Inspired by these elegant

Synthesis and characterizations of highly luminescent 5-isopropoxybenzo[rst]pentaphene

• Islam S. Marae,
• Jingyun Tan,
• Rengo Yoshioka,
• Zakaria Ziadi,
• Eugene Khaskin,
• Serhii Vasylevskyi,
• Ryota Kabe,
• Xiushang Xu and
• Akimitsu Narita

Beilstein J. Org. Chem. 2025, 21, 270–276, doi:10.3762/bjoc.21.19

• by scanning electron microscopy. The intriguing optical properties of BPP and its derivatives may lead to their application as fluorophores. Keywords: benzo[rst]pentaphene; intramolecular charge transfer; nanocrystals; photoluminescence; polycyclic aromatic hydrocarbon; Introduction Polycyclic

• facile access to BPP was reported by Amsharov and co-workers through the so-called "dehydrative π-extension (DPEX)” reaction [12]. However, functionalized derivatives of BPP have scarcely been explored in comparison to the extensive studies on the derivatives of other PAHs, such as pyrene [15][16][17

• -substituted derivatives [21][22]. In comparison to the absorption spectrum of BPP 2, this lowest-energy absorption band of BPP-OiPr 3 was red-shifted by ≈26 nm, which marked the inductive and resonance effects of the electron-donating isopropyloxy group with lone pairs of electrons, raising the HOMO level

Three-component reactions of conjugated dienes, CH acids and formaldehyde under diffusion mixing conditions

• Dmitry E. Shybanov,
• Maxim E. Kukushkin,
• Eugene V. Babaev,
• Nikolai V. Zyk and
• Elena K. Beloglazkina

Beilstein J. Org. Chem. 2025, 21, 262–269, doi:10.3762/bjoc.21.18

• , which should significantly reduce undesirable polycondensations involving CH2O as well as polymerization of the intermediately formed methylidene derivatives. In this work, we generated methylidene adducts by formaldehyde condensation under diffusion mixing conditions in three-component reactions with

• various CH acid derivatives and conjugated dienes (cyclopentadiene, 1,3-cyclohexadiene, 2,3-dimethylbutadiene and isoprene), leading to [4 + 2]-cycloaddition adducts (Scheme 1). It should be noted that in previous works describing three-component reactions of carbonyl compounds, conjugated dienes and

• conditions, we studied the possibility of generating active methylidene derivatives from malonic ester, Meldrum's acid, cyanoacetic acid ester, acetoacetic ester, acetylacetone and 1,3-diphenylpropane-1,3-dione (1). We found that, with the exception of malonic ester, all compounds reacted with formaldehyde

Synthesis of disulfides and 3-sulfenylchromones from sodium sulfinates catalyzed by TBAI

• Zhenlei Zhang,
• Ying Wang,
• Xingxing Pan,
• Manqi Zhang,
• Wei Zhao,
• Meng Li and
• Hao Zhang

Beilstein J. Org. Chem. 2025, 21, 253–261, doi:10.3762/bjoc.21.17

• importance. In the field of disulfide synthesis, the conventional approach mainly involves oxidizing thiols to form disulfides. This process employs various oxidation agents, which can be categorized as nonmetallic and metal derivatives [12][13][14][15][16]. Over the past few years, the implementation of

• (sp2)–H radical sulfenylation of enaminones or chromones has emerged as a popular strategy using various sulfenyl precursors such as thiophenols [38][39][40], sulfonyl hydrazides [41][42], disulfides [43], KSCN [44], S8 [45], methylsulfinyl derivatives [46], sodium sulfinates [47], and thiosulfonates

Effect of substitution position of aryl groups on the thermal back reactivity of aza-diarylethene photoswitches and prediction by density functional theory

• Misato Suganuma,
• Daichi Kitagawa,
• Shota Hamatani and
• Seiya Kobatake

Beilstein J. Org. Chem. 2025, 21, 242–252, doi:10.3762/bjoc.21.16

• push–pull derivatives bearing electron-donating and electron-withdrawing groups at the para-position of the benzene rings are known to exhibit very fast thermal isomerizations [53]. Velasco and co-workers also reported that a pyrimidine-based azophenol exhibits thermal back reaction on the nanosecond

• calculations can be a powerful tool for molecular design. In this work, we newly synthesize various aza-diarylethene derivatives N3, N4, and I1–I4 with different substitution positions of the aryl group, and investigate their photochromic behaviors and thermal back reactivities as the data set for the

• thermal back reactivities on the order of sub-ms to ms as well as N1 and N2. These thermal back reaction rates are comparable to those of diarylbenzene derivatives, hexaarylbiimidazole derivatives, and naphthopyran derivatives, which are known as fast T-type molecules [41][65][66]. Investigating the ΔH

Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles

• Yujun Pang,
• Jinglan Yan,
• Nawaf Al-Maharik,
• Qian Zhang,
• Zeguo Fang and
• Dong Li

Beilstein J. Org. Chem. 2025, 21, 234–241, doi:10.3762/bjoc.21.15

• derivatives exhibit improved pharmacokinetic properties [17], which has further sparked interest in their development. Consequently, constructing benzimidazoles bearing the CF2H and PhCF2 groups has garnered significant attention. However, despite this growing interest, only a limited number of research

Heteroannulations of cyanoacetamide-based MCR scaffolds utilizing formamide

• Marios Zingiridis,
• Danae Papachristodoulou,
• Despoina Menegaki,
• Konstantinos G. Froudas and
• Constantinos G. Neochoritis

Beilstein J. Org. Chem. 2025, 21, 217–225, doi:10.3762/bjoc.21.13

• synthesis was efficient and rapid as the final adducts could be isolated only by precipitation. In addition, the reactions were performed in a parallel setup using custom-made metal blocks. Specifically, thienopyrimidine and thienopyrimidone derivatives exhibit a range of biological activities, i.e

• ., analgesia, anti-inflammation, antihypertension and many more (DB06889, DB07397, DB08777) [47][48][49][50][51][52][53][54][55][56]. Thienopyrimidone derivatives have also been used in the context of other Gewald-based MCRs in the past, but the reported diversity has been rather low [57][58][59][60]. The

• reaction of 2 with formamide was performed within only 3 h (Scheme 3), yielding the N-substituted thienopyrimidones 5a–e in 30–99% total yield (2 steps), as well with aliphatic and (hetero)aromatic substituents. Quinoline derivatives are prevalent in nature, and many exhibit a range of biological

Dioxazolones as electrophilic amide sources in copper-catalyzed and -mediated transformations

• Seungmin Lee,
• Minsuk Kim,
• Hyewon Han and
• Jongwoo Son

Beilstein J. Org. Chem. 2025, 21, 200–216, doi:10.3762/bjoc.21.12

• amidation Recently, Cao and co-workers reported the copper-catalyzed synthesis of 1,2,4-triazole derivatives via an N-acyl nitrene intermediate [76]. As illustrated in Scheme 3, dioxazolones 4 and N-iminoquinolinium ylides 5 served as reactive substrates, leading to the formation of various polycyclic 1,2,4

• -triazole analogues 6. Both dioxazolones 4 and N-iminoquinolinium ylides 5 demonstrated excellent tolerance in this transformation. Notably, electron-rich dioxazolones exhibited slightly higher reactivity. The proposed catalytic cycle for the copper-catalyzed synthesis of 1,2,4-triazole derivatives is

• , styrene derivatives bearing both electron-rich and electron-poor groups underwent the desired transformation with high yields and enantioselectivities (23g and 23h). However, the styrene scaffold bearing a trifluoromethyl group showed reduced enantioselectivity (23i). Styrenes containing heterocyclic

Hydrogen-bonded macrocycle-mediated dimerization for orthogonal supramolecular polymerization

• Wentao Yu,
• Zhiyao Yang,
• Chengkan Yu,
• Xiaowei Li and
• Lihua Yuan

Beilstein J. Org. Chem. 2025, 21, 179–188, doi:10.3762/bjoc.21.10

• , including pyridinium and its derivatives [40]. More importantly, it favors intermolecular π-stacking interactions with aromatic guests [48]. Herein, we report on a novel supramolecular dimerization motif in 2:2 stoichiometry using H-bonded aramide macrocycles for constructing orthogonal supramolecular

Recent advances in electrochemical copper catalysis for modern organic synthesis

• Yemin Kim and
• Won Jun Jang

Beilstein J. Org. Chem. 2025, 21, 155–178, doi:10.3762/bjoc.21.9

• optimized conditions allowed the reaction to proceed under a constant current electrolysis at 1.5 mA for 6 hours, followed by stirring for additional 24 hours with the electricity turned off. These reaction conditions were applicable to various N-aryl-THIQ derivatives with various functional groups. Using

• asymmetric electrocatalytic cyanophosphinoylation of vinylarenes (Figure 14) [69]. In the presence of a copper catalyst and the chiral ligand sBOX(iPr) (L8) in an electrochemical cell, these three component reactions using styrene derivatives 27, TMSCN (21), and diarylphosphine oxide 80 as starting materials

Cu(OTf)₂-catalyzed multicomponent reactions

• Sara Colombo,
• Camilla Loro,
• Egle M. Beccalli,
• Gianluigi Broggini and
• Marta Papis

Beilstein J. Org. Chem. 2025, 21, 122–145, doi:10.3762/bjoc.21.7

• intermediate VIII. At this stage, the amido–copper complex IX selectively attacks the intermediate providing the 1-aryl-2-sulfonamidopropane 8. This procedure is a valuable alternative to a similar approach for the synthesis of amphetamine derivatives 9 from allyl carbamates that requires excess of Cu(OTf)2 [6

• Biginelli reaction was carried out starting from salicylaldehyde providing hydroxyphenyl-substituted dihydropyrimidines 18 [30]. Subsequently, the regioselective oxidation of the dihydropyrimidine ring in the presence of CAN allowed the formation of new pyrimidinone derivatives 19. The efficacy of Cu(OTf)2

• , reacts with an enol species activated by the copper catalyst, affording the final product. The same research group reported an extension of this study by starting from arylacetylenes instead of arylketones [42]. Imidazo[1,2-a]pyridine derivatives 33 can be achieved by Cu(OTf)2-catalyzed multicomponent

Recent advances in organocatalytic atroposelective reactions

• Henrich Szabados and
• Radovan Šebesta

Beilstein J. Org. Chem. 2025, 21, 55–121, doi:10.3762/bjoc.21.6

• compounds comprising a stereogenic plane or axis is much less developed. Axially chiral compounds are well known as chiral ligands in asymmetric catalysis, with notable examples of binaphthyl-based derivatives such as BINAP, SEGPHOS, or binaphthyl-based phosphoric acid derivatives, which are among the

• reacted with aminoarylaldehydes 5 to form axially chiral 2-arylquinoline derivatives 6 (Scheme 2). Using the pyrrolidine derivative C2 as the most efficient organocatalyst, a range of quinoline derivatives were obtained in high yields and enantiomeric purities. The postulated mechanism consists of iminium

• was carried out to provide the final biaryl products 17. In a related strategy, Hayashi´s team realized an organocatalytic Michael/aldol cascade leading to chiral dihydronaphthalene derivatives 20a–e [25]. Through a series of one-pot reactions, aromatization was achieved with concomitant central-to

Facile one-pot reduction of β-nitrostyrenes to phenethylamines using sodium borohydride and copper(II) chloride

• Laura D’Andrea and
• Simon Jademyr

Beilstein J. Org. Chem. 2025, 21, 39–46, doi:10.3762/bjoc.21.4

• atmosphere, special precautions, and with isolated yields up to 60% [14][15]. Due to the formation of side products, final purification of the amino derivatives requires the use of either multiple separation techniques, chromatography, or distillation [15][16][17][18] (Scheme 1). Differently from lithium