Further elaboration of the stereodivergent approach to chaetominine-type alkaloids: synthesis of the reported structures of aspera chaetominines A and B and revised structure of aspera chaetominine B

• Jin-Fang Lü,
• Jiang-Feng Wu,
• Jian-Liang Ye and
• Pei-Qiang Huang

Beilstein J. Org. Chem. 2025, 21, 2072–2081, doi:10.3762/bjoc.21.162

• generation of our synthetic strategy to chaetominine-type alkaloids featuring two modifications of the last step of our 4 to 6-step approach. Firstly, by employing EDCI/HOBt as the coupling system for the last step of the one-pot O-debenzylation–lactamization reaction, the overall yield of our previous total

• Improved five-step total synthesis of (–)-isochaetominine A In our recent communication on the synthesis of versiquinazoline H (11) [65], we uncovered that the employment of EDCI/HOBt as the coupling system for the last step, namely, the O-debenzylation–lactamization reaction, afforded much higher yields

Bioinspired total syntheses of natural products: a personal adventure

• Zhengyi Qin,
• Yuting Yang,
• Nuran Yan,
• Xinyu Liang,
• Zhiyu Zhang,
• Yaxuan Duan,
• Huilin Li and
• Xuegong She

Beilstein J. Org. Chem. 2025, 21, 2048–2061, doi:10.3762/bjoc.21.160

• natural products of the monocerin-family Early in 1979, monocerin and 7-O-demethylmonocerin were elucidated from Fusarium larvarum [20]. Since then, a large group of analogues have been isolated from diverse fungal species [21][22][23][24][25] (Scheme 2). Along with the structural elucidation, biological

• benzylic oxidation to generate a para-quinone methide (pQM) intermediate. Using fusarentin 6-methyl ether as an example, pQM intermediate 10 would be generated. The C10 alcohol should successively undergo an oxa-Michael addition reaction to close the THF ring, providing 7-O-demethylmonocerin. Similarly

• transformation was successfully achieved by using PhI(OAc)2 as oxidant, providing 7-O-demethylmonocerin, containing the cis-substituted THF ring with sole diastereoselectivity. Site-selective mono-methylation gave rise to monocerin. The bioinspired approach successfully found applications in the total synthesis

Switchable pathways of multicomponent heterocyclizations of 5-amino-1,2,4-triazoles with salicylaldehydes and pyruvic acid

• Yana I. Sakhno,
• Oleksander V. Buravov,
• Kostyantyn Yu. Yurkov,
• Anastasia Yu. Andryushchenko,
• Svitlana V. Shishkina and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2025, 21, 2030–2035, doi:10.3762/bjoc.21.158

• substituted salicylaldehydes are particularly interesting because of the possibility of additional reactions and post-cyclizations involving the o-hydroxy group. It was demonstrated [10][11][12] that the multicomponent reaction of substituted 3-amino-1,2,4-triazoles, various salicylaldehydes, and acetone

α-Ketoglutaric acid in Ugi reactions and Ugi/aza-Wittig tandem reactions

• Vladyslav O. Honcharov,
• Yana I. Sakhno,
• Olena H. Shvets,
• Vyacheslav E. Saraev,
• Svitlana V. Shishkina,
• Tetyana V. Shcherbakova and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2025, 21, 2021–2029, doi:10.3762/bjoc.21.157

• Vladyslav O. Honcharov Yana I. Sakhno Olena H. Shvets Vyacheslav E. Saraev Svitlana V. Shishkina Tetyana V. Shcherbakova Valentyn A. Chebanov Institute of Functional Materials Chemistry, State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, Nauky

• library of bis- and tetraamides was synthesized by the Ugi reaction with α-ketoglutaric acid, tert-butyl isocyanide, aromatic aldehydes, and aromatic amines. When o-azidoanilines were used, azidated peptidomimetics were obtained, the post-cyclization of which by the aza-Wittig reaction yielded a series of

• prepare new quinoxalinone derivatives, we studied a tandem combination of Ugi/aza-Wittig reactions involving α-ketoglutaric acid and o-azidoanilines. First, 5-((2-arylazido)(1-aryl-2-(tert-butylamino)-2-oxoethyl)amino)-4,5-dioxopentanoic acids 8a,b,d,f–h were synthesized by the reaction of KGA (1

Aryl iodane-induced cascade arylation–1,2-silyl shift–heterocyclization of propargylsilanes under copper catalysis

• Rasma Kroņkalne,
• Rūdolfs Beļaunieks,
• Armands Sebris,
• Anatoly Mishnev and
• Māris Turks

Beilstein J. Org. Chem. 2025, 21, 1984–1994, doi:10.3762/bjoc.21.154

• stabilized allyl cation intermediates that undergo regioselective trapping by internal O- and N-nucleophiles furnishing functionalized heterocycles. This method provides access to tetrahydrofuran or pyrrolidine frameworks, each bearing a trifunctionalized (E)-configured vinyl side chain. The use of a shorter

• reaction [17] and a [4 + 2] annulation reaction between o-carboxylic ester-containing diaryl-λ3-iodanes and some terminal alkynes [18]. Looking to expand the possibilities for terminal alkyne carbofunctionalization, we turned our attention to propargylsilanes, which are prone to undergo cationic

• previous work [22]. The internal O-nucleophile-containing starting material, 4-(tert-butyldimethylsilyl)hex-5-yn-1-ol (7d), was obtained from the commercial hex-5-yn-1-ol by a O-silylation and subsequent retro-Brook reaction sequence [29]. Arylation of silane 7d with 1.2 equiv PhMesIOTf (I-1), 5 mol % CuCl

Photochemical reduction of acylimidazolium salts

• Michael Jakob,
• Nick Bechler,
• Hassan Abdelwahab,
• Fabian Weber,
• Janos Wasternack,
• Leonardo Kleebauer,
• Jan P. Götze and
• Matthew N. Hopkinson

Beilstein J. Org. Chem. 2025, 21, 1973–1983, doi:10.3762/bjoc.21.153

• research has demonstrated that NHCs are also capable of stabilizing radical or excited-state species [12][13]. In 2020, our group reported the concept of photo-NHC catalysis where direct excitation of acylazolium intermediates generated from o-toluoyl fluoride substrates with UV-A light resulted in a novel

• catalytic photoenolization/Diels–Alder (PEDA) reaction [14][15]. In this process, the NHC fragment present in the acylazolium species influences the absorption wavelength and fundamental photochemical reactivity of the C=O bond, enabling a “ketone-like” photoreaction from otherwise unsuitable carboxylic

• %) and BzO− (43%), additional signals consistent with the O-benzoylated species 3 were identified. This compound was synthesized independently from benzoyl chloride and 1-methylimidazole (see Supporting Information File 1) with spiking of the crude 1H NMR spectrum with the authentic sample confirming the

Asymmetric total synthesis of tricyclic prostaglandin D2 metabolite methyl ester via oxidative radical cyclization

• Miao Xiao,
• Liuyang Pu,
• Qiaoli Shang,
• Lei Zhu and
• Jun Huang

Beilstein J. Org. Chem. 2025, 21, 1964–1972, doi:10.3762/bjoc.21.152

• a single diastereomer (Table 1, entry 4). To explain this diastereoselectivity, we hypothesize that the C–O bond, which occupies an axial position in the proposed transition state TS-1, could avert an additional hyperconjugative interaction (σ*C-O/π) that renders the reacting C=C bond electron

Enantioselective desymmetrization strategy of prochiral 1,3-diols in natural product synthesis

• Lihua Wei,
• Rui Yang,
• Zhifeng Shi and
• Zhiqiang Ma

Beilstein J. Org. Chem. 2025, 21, 1932–1963, doi:10.3762/bjoc.21.151

• underwent a reductive interrupted Fisher indolization with phenylhydrazine to give indoline 281. To forge the C16 stereocenter and form the C–O bond at C2, diol 282 was prepared from 281 in six steps. Treatment of 282 with MeI/Cs2CO3 induced cyclization through putative indoleninium intermediate 283

Rhodium-catalysed connective synthesis of diverse reactive probes bearing S(VI) electrophilic warheads

• Scott Rice,
• Julian Chesti,
• William R. T. Mosedale,
• Megan H. Wright,
• Stephen P. Marsden,
• Terry K. Smith and
• Adam Nelson

Beilstein J. Org. Chem. 2025, 21, 1924–1931, doi:10.3762/bjoc.21.150

• -substrates with the potential to react with metal carbenoids in many different ways [14], for example through O–H, N–H or formal C–H insertion, cyclopropanation, or oxazole [20] formation. The 16 co-substrates, selected from available compounds in our laboratory, are shown in Figure 2 (panel A). Many of

• these substrates had more than one potentially reactive site to enable, for example, O–H insertion (C1–5, C8, C11 and C14), N–H insertion (C3, C6, C12, C13 and C15), formal C–H insertion (C1, C3, C4, C12, C15 and C16), oxazole formation (C9 and C10) and cyclopropanation (C7, C10, C14 and C16). To start

• reactions, a product with molecular weight consistent with O–H insertion into water was also observed. For these 18 substrate/co-substrate combinations, the reaction with the highest estimated yield was selected for mass-directed purification (Table 2). In total, 23 intermolecular reaction products were

Synthesis, biological and electrochemical evaluation of glycidyl esters of phosphorus acids as potential anticancer drugs

• Almaz A. Zagidullin,
• Emil R. Bulatov,
• Mikhail N. Khrizanforov,
• Damir R. Davletshin,
• Elvina M. Gilyazova,
• Ivan A. Strelkov and
• Vasily A. Miluykov

Beilstein J. Org. Chem. 2025, 21, 1909–1916, doi:10.3762/bjoc.21.148

• chemical literature regarding the biological activity (including anticancer properties) of phosphoric esters, reports on biological studies of systems based on the P=O fragment and oxirane skeletons are less common. Nevertheless, systems containing both of the mentioned structural motifs are rarely

• of chlorophosphine oxides (methylphosphonic dichloride MeP(O)Cl2; methyl dichlorophosphate (MeO)P(O)Cl2) and phosphorus oxychloride P(O)Cl3 with racemic glycidol in CH2Cl2 in the presence of KOH as basic agent (Scheme 1). Further filtration and final distillation at low pressure leads to the products

• voltammetric wave, the aqueous solution was actively stirred with a magnetic stirrer in an atmosphere of constant inert gas flow. Starting materials. Methylphosphonic dichloride MeP(O)Cl2 and methyl dichlorophosphate (MeO)P(O)Cl2) [30] were prepared according to literature procedures. Phosphorus oxychloride P

Chiral phosphoric acid-catalyzed asymmetric synthesis of helically chiral, planarly chiral and inherently chiral molecules

• Wei Liu and
• Xiaoyu Yang

Beilstein J. Org. Chem. 2025, 21, 1864–1889, doi:10.3762/bjoc.21.145

• catalytic sites. The OH group on the phosphorus atom functions as a Brønsted acid site, while P=O serves as a Lewis base site, which enables the simultaneous activation of both nucleophiles and electrophiles in one reaction (Figure 1). The chiral properties of the catalysts are derived from the chiral

• macrocyclization strategy [53]. Starting from the linear precursor 60 bearing two triazine moieties, the intramolecular SNAr reaction catalyzed by CPA 13 (30 mol %) led to macrocyclization, which produced the inherently chiral N3,O-calix[2]arene[2]triazines 61 with high enantioselectivity, albeit in moderate yield

• ]arenes displayed a distinctive 1,3-alternate conformation, notably differing from the typical cone conformation of the conventional calix[4]arenes. Moreover, unlike previously documented examples, the inherent chirality of these products arises from the difference of just one heteroatom (O and NH) in the

Photoswitches beyond azobenzene: a beginner’s guide

• Michela Marcon,
• Christoph Haag and
• Burkhard König

Beilstein J. Org. Chem. 2025, 21, 1808–1853, doi:10.3762/bjoc.21.143

• symmetrical diazocines is more demanding compared to classical azobenzenes since the two aromatic rings are not only connected via an azo-bond, but also have to be linked by an alkyl chain first. For that, more synthetic effort is required. It can be performed through oxidative dimerisation of o-nitrotoluene

• (37) followed by reduction with Zn/Ba(OH)2 and partial re-oxidation (Scheme 12A) [52]. They can also be obtained from o-halogenated benzyl bromides 40 by lithium–halogen exchange followed by nucleophilic substitution and a second lithium–halogen exchange with iodine (Scheme 12B) or by nickel-catalysed

• reaction can also be used to prepare precursors for the Ullman–Goldberg coupling (Scheme 12B and 12C); however, in the presence of halogens, an alternative reduction pathway of the alkene with tosylhydrazine and NaOAc must be used [55]. Hetereodiazocines 35b and 35c are synthesised by coupling of o

[3 + 2] Cycloaddition of thioformylium methylide with various arylidene-azolones in the synthesis of 7-thia-3-azaspiro[4.4]nonan-4-ones

• Daniil I. Rudik,
• Irina V. Tiushina,
• Anatoly I. Sokolov,
• Alexander Yu. Smirnov,
• Alexander R. Romanenko,
• Alexander A. Korlyukov,
• Andrey A. Mikhaylov and
• Mikhail S. Baranov

Beilstein J. Org. Chem. 2025, 21, 1791–1798, doi:10.3762/bjoc.21.141

• transformations. For example, compound 7e underwent both sulfone formation and S/O atoms exchange in the heterocyclic core. For derivatives 6 and 8, any oxidation conditions resulted in even more complex product mixtures (presumably due to the additional sulfur atom in the second ring), whose structures could not

Research progress on calixarene/pillararene-based controlled drug release systems

• Liu-Huan Yi,
• Jian Qin,
• Si-Ran Lu,
• Liu-Pan Yang,
• Li-Li Wang and
• Huan Yao

Beilstein J. Org. Chem. 2025, 21, 1757–1785, doi:10.3762/bjoc.21.139

Unique halogen–π association detected in single crystals of C–N atropisomeric N-(2-halophenyl)quinolin-2-one derivatives and the thione analogue

• Mai Uchibori,
• Nanami Murate,
• Kanako Shima,
• Tatsunori Sakagami,
• Ko Kanehisa,
• Gary James Richards,
• Akiko Hori and
• Osamu Kitagawa

Beilstein J. Org. Chem. 2025, 21, 1748–1756, doi:10.3762/bjoc.21.138

• through a σ-type intermolecular halogen bonding (C–Br···O) between the ortho-bromine atom and the carbonyl oxygen. The formation of similar heterochiral polymers through a σ-type intermolecular halogen bond (C–Br···S) was also found in crystals of the thio-analogue rac-II. On the other hand, in the

• intermolecular interaction (halogen bonding) between chiral compounds possessing an amide group and a thioamide group are quite rare [21]. We were curious as to whether the chirality (racemate/optically pure form)- and the functional group (C=O/C=S)-dependent halogen bonds found in I and II are also observed in

• mebroqualone rac-I was very similar to that of the thione analogue rac-II [the formation of heterochiral polymers through a σ-type halogen bond (C–Br···O or C–Br···S)]. In contrast, the intermolecular associations in the crystals of racemic quinoline-2-thione rac-2a significantly differed from those of the

Preparation of a furfural-derived enantioenriched vinyloxazoline building block and exploring its reactivity

• Madara Darzina,
• Anna Lielpetere and
• Aigars Jirgensons

Beilstein J. Org. Chem. 2025, 21, 1737–1741, doi:10.3762/bjoc.21.136

• methoxymethyl group cleavage, O-to-N rearrangement, and isomerization of the double bond. An oxazoline ring formation in the resulting unsaturated amides provided the corresponding enantioenriched vinyloxazoline. The reactivity of the electron-deficient double bond in the vinyloxazoline was explored in several

• ][24] (Scheme 1). The proposed strategy relied on the N-deprotection of the intermediate ester 3d inducing O-to-N rearrangement to form amide 5 as a precursor of vinyloxazoline 6. For this purpose, Alloc (allyloxycarbonyl) turned out to be a suitable N-protecting group as it was compatible with the

3,3'-Linked BINOL macrocycles: optimized synthesis of crown ethers featuring one or two BINOL units

• Somayyeh Kheirjou,
• Jan Riebe,
• Maike Thiele,
• Christoph Wölper and
• Jochen Niemeyer

Beilstein J. Org. Chem. 2025, 21, 1719–1729, doi:10.3762/bjoc.21.134

• ]. However, under the same coupling conditions (Pd2(dba)3, P(o-Tol)3, n-Bu4N+OH−, toluene/H2O, 90 °C), the reaction of diiodide 1 with bisboronic acids 75/6/7/8 gave only low yields of the desired macrocycles Me-M1 (7/32/22/21% for Me-M15/6/7/8). Thus, the macrocyclization via two-fold Suzuki coupling was

• routes towards macrocycles featuring one BINOL unit. a) Two-fold Suzuki coupling and b) two-fold Williamson synthesis. Reagents and conditions: i) bis(boronic ester) 75/6/7/8 (1.0. equiv), Pd2(dba)3 (0.1 equiv), P(o-Tol)3 (0.2 equiv), n-Bu4N+OH− (3.2. equiv), toluene/H2O 5:1, 90 °C; ii) ethylene glycol

• shown. Initially attempted route towards bis-BINOL macrocycles based on precursors Me-36 or Me-46. Conditions: i) 96 (2.2 equiv), Pd2(dba)3 (0.1 equiv), P(o-Tol)3 (0.2 equiv), n-Bu4N+OH− (3.2 equiv), toluene/H2O 5:1, 90 °C; ii) 96 (2.2. equiv), Cs2CO3 (3.0 equiv), CH3CN, 80 °C. Synthetic route towards

Approaches to stereoselective 1,1'-glycosylation

• Daniele Zucchetta and
• Alla Zamyatina

Beilstein J. Org. Chem. 2025, 21, 1700–1718, doi:10.3762/bjoc.21.133

• typically exist as a mixture of anomers which complicates their use in the chemical glycosylation reactions. Earlier approaches to constructing 1,1'-O-glycosidic bonds often relied on the use of simply and symmetrically protected (benzylated or acetylated) monosaccharide building blocks, enabling the

• tetrabenzylated glucose lactol acceptor 2, resulting in the formation of the β,α-1,1-linked diglucoside 3 (Scheme 1) [49]. The application of a the 2,3,4,6-tetra-O-benzyl trichloroacetimidate donor 4 resulted in the same disaccharide product 3, albeit as part of a mixture with other diastereomers [51]. The

• formation of an α-glycoside on the donor side [54]. On the acceptor side, the β-configuration was favored due to steric hindrance from the C-2 phthalimido group in the triacetylated GalN-lactol acceptors 6 or 3,4-di-O-benzylated acceptors 8, resulting in kinetically controlled formation of β,α-1,1

Continuous-flow-enabled intensification in nitration processes: a review of technological developments and practical applications over the past decade

• Feng Zhou,
• Chuansong Duanmu,
• Yanxing Li,
• Jin Li,
• Haiqing Xu,
• Pan Wang and
• Kai Zhu

Beilstein J. Org. Chem. 2025, 21, 1678–1699, doi:10.3762/bjoc.21.132

• classifications necessitate tailored nitrating reagent selections, giving rise to fundamentally distinct mechanistic pathways. This reactivity is exemplified by the comparative kinetic profiles: N-nitration of amines and O-nitration of alcohols – facilitated by accessible lone electron pairs – exhibit markedly

• , achieving 54.98% o- and 45.01% p-nitrophenol yields within 15 minutes [10]. Umrigar et al. demonstrated a microwave-assisted nitration of monochlorobenzene (MCB) for the efficient synthesis of 2,4-dinitrochlorobenzene (2,4-DNCB), achieving reduced reaction time, minimized waste acid, and enhanced yield

• nitric acid and the model was formulated to predict the reaction outcome at large capacity. Lan and Lu [32] developed a method for the rapid determination of lumped kinetics for the nitration of o-dichlorobenzene by processing the profile of adiabatic temperature rise in a micropacked-bed reactor. Type B

Structural analysis of stereoselective galactose pyruvylation toward the synthesis of bacterial capsular polysaccharides

• Tsun-Yi Chiang,
• Mei-Huei Lin,
• Chun-Wei Chang,
• Jinq-Chyi Lee and
• Cheng-Chung Wang

Beilstein J. Org. Chem. 2025, 21, 1671–1677, doi:10.3762/bjoc.21.131

• modifications of bacterial polysaccharides, and the interaction of 4,6-O-pyruvylated pyranoses with lectins depends on the stereochemistry of the pyruvate ketal. Moreover, this chemical modification is crucial, as the distinct R or S diastereochemistry at the ketal center directly influences its biological

• confirming their structure by using X-ray crystallography as direct evidence. Subsequently, the pyruvylated galactose was further applied in the synthesis of zwitterionic polysaccharide A1 (PS A1) precursor. Results and Discussion In the initial experiment, p-tolyl 2,3-di-O-acetyl-1-thio-β-galactopyranoside

• a = 16.1017(4) Å, b = 7.7608(2) Å, c = 28.8344(8) Å, and β = 93.3680(10)°. Additionally, the presence of lattice water greatly influenced the molecular packing. The hydrogen bond (H–O–H) lengths in this lattice water ranged from 1.923 to 2.204 Å (Figure 2b). The pyruvylated galactose 6 was utilized

Catalytic asymmetric reactions of isocyanides for constructing non-central chirality

• Jia-Yu Liao

Beilstein J. Org. Chem. 2025, 21, 1648–1660, doi:10.3762/bjoc.21.129

• reductive elimination to afford INT-IV. Finally, migration of the Piv group from O to N gave the product 17a. Moreover, the Pd-catalyzed isocyanide insertion approach has been successfully extended to the generation of helical chirality [31]. As shown in Scheme 4a, phenyl diisocyanides 21 or 22 underwent

• thionolactones, getting rid of the pre-formation of stoichiometric Ru-complexes [52][53]. Mechanistic investigations indicated that this transformation proceeds through a two-step sequence promoted by the same catalyst: 1) the diastereo- and enantioselective [3 + 2] cycloaddition to generate spiro-S,O-ketal 52

On the aromaticity and photophysics of 1-arylbenzo[a]imidazo[5,1,2-cd]indolizines as bicolor fluorescent molecules for barium tagging in the study of double-beta decay of ¹³⁶Xe

• Eric Iván Velazco-Cabral,
• Fernando Auria-Luna,
• Juan Molina-Canteras,
• Miguel A. Vázquez,
• Iván Rivilla and
• Fernando P. Cossío

Beilstein J. Org. Chem. 2025, 21, 1627–1638, doi:10.3762/bjoc.21.126

• rigid, with only small modifications on going from the ground state to the first single excited state (Figure 6). However, the presence of the two perchlorate anions results in additional coordination with Ba2+, thus resulting in larger values of the Ba–N distances, as well as of the average Ba–O and Ba

• [33] calculations were performed using the B3LYP[34][35][36], B3LYP-D3BJ [37][38], CAM-B3LYP [39], M06 [40][41], M06-2X [42], M06-L [43][44][45], PBE0 [46] and ωB97XD [47] functionals. The 6-311+G* and 6-31++G** bases sets [48][49] were used for C, N, O, and H. The DefTZVPP [50] effective-core

• (⟨RBa0⟩)n denote the average Ba–O bond distances (in Å) for the different crown ethers. Distances between Ba2+ and the ring points of electron density of benzene (in green) are also gathered in (B). ΔGiso and ΔGrxn terms stand for the Gibbs energies (in kcal/mol) described in Scheme 2 and have been

Transition-state aromaticity and its relationship with reactivity in pericyclic reactions

• Israel Fernández

Beilstein J. Org. Chem. 2025, 21, 1613–1626, doi:10.3762/bjoc.21.125

• associated with high barriers (>40 kcal/mol). However, we found that the Meerwein–Ponndorf–Verley-type reaction involving the double hydrogen migration from CH3–OH to O=CH2 proceeds with a much lower activation barrier of ca. 25 kcal/mol [79]. Interestingly, although the analogous reaction involving CH3–CH3

• and O=CH2 proceeds with a much higher barrier, both transformations feature transition states whose in-plane aromaticity is nearly identical according to their NICS(3, +1) values (−24.5 ppm vs −27.2 ppm, respectively). Therefore, it is found once again that there is no clear relationship between the

• TS-aromaticity and the barrier heights. The origin of the computed decrease of the activation barrier in the CH3–OH to O=CH2 as compared to the analogous reaction involving ethane as hydrogen donor can be initially traced to different C–H vs O–H bond strengths. Indeed, we found that the total bond

Chemical synthesis of glycan motifs from the antitumor agent PI-88 through an orthogonal one-pot glycosylation strategy

• Shaokang Yang,
• Xingchun Sun,
• Hanyingzi Fan and
• Guozhi Xiao

Beilstein J. Org. Chem. 2025, 21, 1587–1594, doi:10.3762/bjoc.21.122

• ABz 7, Man PVB 8, and Man 9 through orthogonal one-pot glycosylation strategy (Scheme 1B). The 2-O-Bz group in 5–8 served as the neighboring participating group for the stereoselective construction of 1,2-trans-mannosidic bonds, while the 3-O-Lev group in 6 was the temporary protecting group for (1→3

Thermodynamic equilibrium between locally excited and charge transfer states in perylene–phenothiazine dyads

• Issei Fukunaga,
• Shunsuke Kobashi,
• Yuki Nagai,
• Hiroki Horita,
• Hiromitsu Maeda and
• Yoichi Kobayashi

Beilstein J. Org. Chem. 2025, 21, 1577–1586, doi:10.3762/bjoc.21.121

• local excited (LE) and charge-transfer (CT) states can be experimentally observed as dual fluorescence: a structured, higher-energy emission from the LE state and a broad, red-shifted emission from the CT state [8][9]. Classical systems such as 4-(N,N-dimethylamino)benzonitrile (DMABN) and pyrene-o