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Search for "intermediate" in Full Text gives 2200 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Get a better glimpse on sequential photoreactions of trisnorbornadienes with 19F NMR spectroscopy

  • Julian Felix Maria Hebborn,
  • Ben Eric Merten,
  • Thomas Paululat and
  • Heiko Ihmels

Beilstein J. Org. Chem. 2026, 22, 527–534, doi:10.3762/bjoc.22.38

Graphical Abstract
  • trisquadricyclane. Even though the reaction can be monitored by photometry or by in situ 1H NMR spectroscopy, unambiguous assignment of the distinct intermediate mono- and bisquadricyclanes was not possible because of signal overlap. In contrast, this shortcoming is circumvented with in situ 19F NMR-spectroscopic
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Published 23 Mar 2026

Modern synthetic pathways towards eribulin and its subunits

  • Sebastian Dominik Graf

Beilstein J. Org. Chem. 2026, 22, 495–526, doi:10.3762/bjoc.22.37

Graphical Abstract
  • proved to be suitable for the cyclization towards 35 and the eventual macrocyclization was achieved via coupling of the alkyl bromide unit with the thioester. Mechanistically, this reaction is enabled by the formation of an intermediate alkylzinc halide, which is produced by single electron transfer
  • described in Scheme 6 below (R1 and R2 in equatorial position). From 43, the methylene unit in 44 was formed by Pd(0)-mediated generation of a π-allyl–palladium intermediate, followed by reductive termination (Tsuji-reduction), alongside the substrate-controlled alignment of the adjacent methyl substituent
  • . Protection of the free alcohol unit enabled the transformation towards 55, which involved the reduction of lactone to lactole, protection of the alcohol as acetate, BF3·Et2O-mediated C-allylation of the aldehyde (via oxocarbenium intermediate) and cyclization (oxy-Michael reaction). Hydroboration–oxidation
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Published 19 Mar 2026

Synthesis and uranyl(VI) extraction performance of a calix[4]pyrrole–tetrahydroxamic acid receptor

  • Sara Karnib,
  • Rana Baydoun,
  • Wissam Zaidan,
  • Nancy AlHaddad,
  • Omar El Samad,
  • Bilal Nsouli,
  • Francine Cazier-Dennin and
  • Pierre-Edouard Danjou

Beilstein J. Org. Chem. 2026, 22, 486–494, doi:10.3762/bjoc.22.36

Graphical Abstract
  • both for the generation of free hydroxylamine and for the subsequent synthesis of PCP HA. The resulting tetrapotassium hydroxamate intermediate was then acidified with a 10% HCl solution, inducing precipitation of the tetrahydroxamic acid form. PCP HA was isolated as a grey solid in high yield (95
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Published 18 Mar 2026

Synthesis of a HDAC inhibitor–nanogold probe for cryo-EM visualization in class I HDAC co-repressor complexes

  • Wiktoria A. Pytel,
  • John W. R. Schwabe and
  • James T. Hodgkinson

Beilstein J. Org. Chem. 2026, 22, 480–485, doi:10.3762/bjoc.22.35

Graphical Abstract
  • dibenzylated by-product. Compound 5 was then coupled to the CI-994 intermediate 3 via HATU-mediated amide bond formation to produce 6 in good yield. Removal of the benzyl protecting group was performed by catalytic hydrogenation and acid 7 was obtained in near quantitative yield. Intermediate 7 was converted
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Published 17 Mar 2026

Recent advances in the stereoselective synthesis of distal biaxially chiral molecules

  • Fanxing Zhou,
  • Chen Zhang,
  • Lingyu Sun,
  • Yiyun Fang,
  • Siming Zheng,
  • Lina Hu,
  • Mengyang Shen,
  • Zhen Zhao,
  • Wei Xu,
  • Yunqiang Sun and
  • Zi-Qiang Rong

Beilstein J. Org. Chem. 2026, 22, 461–479, doi:10.3762/bjoc.22.34

Graphical Abstract
  • synthesis of 1,4-divinyl compounds 24 containing a 2,3-diol motif via a vinylogous quinone methide (VQM) intermediate (Scheme 5) [46]. The transformation exhibited excellent stereoselectivity, and preliminary studies showed that the products could be elaborated into novel axially chiral scaffolds with
  • ) intermediate, which undergoes intramolecular nucleophilic cyclization (Scheme 15) [54]. This work represents the first synthesis of a compound integrating both helical and axial stereogenic elements, and achieves high diastereoselectivity and enantioselectivity through a cinchona alkaloid-derived squaramide
  • organocatalytic approach. The mechanistic study revealed that the reaction proceeds through a stepwise double cyclization process: The first cyclization generates an intermediate bearing a stereogenic axis, while the second cyclization involves dynamic kinetic resolution of the spiral reaction intermediate under
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Published 16 Mar 2026

Structural reassignment of compound 968, an allosteric glutaminase inhibitor

  • Lindsey A. Albertelli,
  • Sainabou Jallow,
  • Chun Li and
  • Scott M. Ulrich

Beilstein J. Org. Chem. 2026, 22, 455–460, doi:10.3762/bjoc.22.33

Graphical Abstract
  • oxidatively deaminated to the TCA cycle intermediate α-ketoglutarate for energy production and additional biosynthetic pathways. There are two glutaminase isozymes in humans: KGA is encoded by the GLS1 gene and is expressed mainly in the kidney and brain and LGA encoded by the GLS2 gene is expressed mainly in
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Published 13 Mar 2026

A facile and practical method for the synthesis of trans-(±)-taxifolin and its derivatives via Darzens reaction

  • Bo Peng,
  • Panpan Yang,
  • Maaz Khan,
  • Xiaotong Lin,
  • Jiang Wu,
  • Peng Fu and
  • Qingqing Wu

Beilstein J. Org. Chem. 2026, 22, 443–450, doi:10.3762/bjoc.22.31

Graphical Abstract
  • give protected acetophenone 1 in an excellent yield of 78%. Next, the reaction conditions for the following α-bromination of acetophenone 1 to intermediate 2 were screened (Table S1, Supporting Information File 1). The treatment of compound 1 with CuBr2 in EtOAc at either room temperature or 60 °C
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Published 12 Mar 2026

Synthesis and stereochemical analysis of dynamic planar chiral oxa[7]orthocyclophene

  • Yukiho Hashimoto,
  • Yuuya Kawasaki,
  • Kazunobu Igawa and
  • Katsuhiko Tomooka

Beilstein J. Org. Chem. 2026, 22, 436–442, doi:10.3762/bjoc.22.30

Graphical Abstract
  • -substituted oxacyclophenes 1ab (X = O, Y = Me), 1ac (X = O, Y = Ph), and 1ad (X = O, Y = I), in which 1ad was used as the key intermediate for the synthesis of 1ab and 1ac via Kumada–Tamao coupling with Grignard reagents (Figure 2). Results and Discussion Retrosynthesis and synthesis of the C6-iodo
  • and revealed their dynamic planar chirality. By using the C6-iodo-substituted oxacyclophene as a common intermediate, C6-methyl- and C6-phenyl-substituted oxacyclophenes were synthesized efficiently. The enantiomers of the iodo- and methyl-substituted oxacyclophenes are isolable yet interconvertible
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Published 11 Mar 2026

Dialkylaminoalkylation of β-ketosulfones via ring-opening of 3-sulfonylpyrrolidines

  • Evgeny M. Buev,
  • Alexander V. Pavlushin,
  • Vladimir S. Moshkin and
  • Vyacheslav Y. Sosnovskikh

Beilstein J. Org. Chem. 2026, 22, 383–389, doi:10.3762/bjoc.22.26

Graphical Abstract
  • modifications and the use of the obtained compounds as building blocks. We also examined other nucleophiles suitable for the described domino-sequence. Thus, application of ethanol as solvent resulted in a mixture of the desired product 4b with the corresponding intermediate C (NMR ratio 88:12), however, longer
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Published 03 Mar 2026

Electrosynthetic access to unsymmetrical oxaza[8]helicenes with high chiral stability and strong circularly polarized luminescence (CPL)

  • Tin Zar Aye,
  • Rubal Sharma,
  • Muthu Karuppasamy,
  • Daiya Suzuki,
  • Haruka Nakajima,
  • Yoshitane Imai,
  • Mitsuhiro Arisawa,
  • Mohamed S. H. Salem and
  • Shinobu Takizawa

Beilstein J. Org. Chem. 2026, 22, 372–382, doi:10.3762/bjoc.22.25

Graphical Abstract
  • = 0.735 V vs Fc/Fc+ in CH2Cl2) is oxidized more readily than the 2-naphthol partners (Eox of 4a = 1.081 V and Eox of 4b = 1.286 V vs Fc/Fc+ in CH2Cl2). The radical cation [3]·+ then undergoes rapid deprotonation to form a neutral radical intermediate (Int-I) with high spin density at the reactive site
  • the pKa of [3]·+ radical cation and spin density of neutral radical intermediate Int-I (optimized at the UB3LYP/6-31G+(d,p) level of theory with IEPCM model as solvation of DCM. Grimme’s dispersion with the original D3 damping function was applied as empirical dispersion correction to the optimized
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Published 25 Feb 2026

Recent advances in the cleavage of non-activated amides

  • Eun-Sol Choi and
  • Hyo-Jun Lee

Beilstein J. Org. Chem. 2026, 22, 352–369, doi:10.3762/bjoc.22.23

Graphical Abstract
  • geometry to the amide unit (Scheme 1a) [17][18][19]. As a result, nucleophilic attack at the carbonyl is disfavored, and even when a tetrahedral intermediate forms, collapse with expulsion of an amide anion is thermodynamically challenging. Consequently, harsh conditions such as high temperatures or
  • intermediate E, the carboxylic acid is formed, regenerating the acidic and basic surface sites of the Nb2O5 catalyst. In 2020, Mashima et al. reported an intriguing accelerating effect of potassium alkoxides on the manganese-catalyzed esterification of tertiary amides (Scheme 4) [48]. They found that potassium
  • % yield. Mechanistically, WCl6 coordinates with Phen to generate the active tungsten species [G]. In cooperation with TMSCl as a Lewis acid, the catalyst activates the amide toward nucleophilic attack by forming an electron-deficient intermediate H that readily undergoes substitution. Palladium complexes
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Published 19 Feb 2026

Ring contraction and ring expansion reactions in terpenoid biosynthesis and their application to total synthesis

  • Nicolas Kratena,
  • Nicolas Heinzig and
  • Peter Gärtner

Beilstein J. Org. Chem. 2026, 22, 289–343, doi:10.3762/bjoc.22.21

Graphical Abstract
  • rise to the isomeric terpin-4-yl cation 6b. By way of cyclopropane formation, a different, so called, thujyl cation 6c is conceivable. Elimination then furnishes the ring-contracted 5/3-ring systems from the original cyclohexyl intermediate to give sabinene (7) and α-thujene (8). Another example of a 6
  • vetispiradiene synthase (HVS) gives the eudesmane cation 10a, which is a common intermediate in the biosynthesis of bicyclic sesquiterpenes, e.g., aristocholenes. In this particular enzymatic reaction, the 1,2-alkyl shift of a Wagner–Meerwein rearrangement is responsible for building up the spirocyclic carbon
  • found in pseudolaric acid B (14) biosynthesis [64][65]. In this case, the linear precursor 12 is first cyclised to give intermediate 14a akin to the α-terpinyl cation (see Scheme 3). From here, quantum chemical calculations indicate that the subsequent 1,2-alkyl shift and olefin cyclisation occur in a
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Published 17 Feb 2026

Spirobarbiturates with a pyrrolizidine moiety: synthesis, structure and biological evaluation

  • Arthur A. Puzyrkov,
  • Andrew S. Drachuk,
  • Ekaterina A. Popova,
  • Alexander V. Stepakov and
  • Vitali M. Boitsov

Beilstein J. Org. Chem. 2026, 22, 274–288, doi:10.3762/bjoc.22.20

Graphical Abstract
  • and α-amino acids, which includes a stage of decarboxylation of the intermediate lactone. It is worth noting that generating azomethine ylides via decarboxylation of α-amino acid derivatives is a common practice in synthetic chemistry [44][45][46]. It was shown in our recent works that spirocyclopropa
  • unable to isolate individual products either by chromatography or by recrystallization. The proposed reaction mechanism is shown in Scheme 5, where it can be seen that the intermediate azomethine ylide, acting as a 1,3-dipole, undergoes a [3 + 2] cycloaddition with N-substituted maleimides 3a–p. The
  • formation of azomethine ylide from alloxan (1) and ʟ-proline (2) was previously studied using DFT calculations [43]. Based on the calculated data, it was assumed that the 1,3-dipole is formed as a result of a multistage sequence: initial generation of a zwitterionic imine intermediate from 1 and 2, followed
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Published 17 Feb 2026

Arene activation via π-bond localization: concepts and opportunities

  • Paul Meiners,
  • Julian J. Melder and
  • Tobias Morack

Beilstein J. Org. Chem. 2026, 22, 257–273, doi:10.3762/bjoc.22.19

Graphical Abstract
  • -coordination of pyrrole transforms the aromatic framework into an azomethine ylide intermediate. This reactive species can engage in a [3 + 2] cycloaddition with activated olefins such as maleic anhydride to form 7-azabicycloheptene complex 8 rather than an electrophilic addition product. An analogous scenario
  • during subsequent electrophilic addition. Although the trifluorotoluene complex exists as a mixture of its two coordination diastereomers, the pronounced electronic asymmetry of the molybdenum fragment channels protonation to a single η2-arenium intermediate. This enables nucleophilic addition of a
  • step, thereby steering the reaction along the para-functionalization pathway. A distinct and less frequently encountered pathway enables ortho-functionalization of arenes via intermediate η3-benzyl complex formation. Yamamoto and co-workers first showcased this in 2008 (Figure 10B), demonstrating the
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Published 09 Feb 2026

A mild and atom-efficient four-component cascade strategy for the construction of biologically relevant 4-hydroxyquinolin-2(1H)-one derivatives

  • Dmitrii A. Grishin,
  • Kseniia I. Sharkovskaia,
  • Ilya G. Kolmakov,
  • Daria A. Ipatova,
  • Rostislav A. Petrov,
  • Nikolai D. Dagaev,
  • Dmitry A. Skvortsov,
  • Maria G. Khrenova,
  • Valeriy V. Andreychev,
  • Sergei A. Evteev,
  • Yan A. Ivanenkov,
  • Roman L. Antipin,
  • Olga А. Dontsova and
  • Elena K. Beloglazkina

Beilstein J. Org. Chem. 2026, 22, 244–256, doi:10.3762/bjoc.22.18

Graphical Abstract
  • (Scheme 3) involved the optimization of a two-step procedure reported previously for their preparation from corresponding anilines and malonic ester [40][41][42][43]. The intermediate N1,N3-bis(4-halogenophenyl)malonamides 1a–c were synthesized from 4-halogen-substituted anilines and diethyl malonate in
  • yields (Scheme 5). The proposed mechanism of the four-component reaction is illustrated in Scheme 6. ʟ-Proline, via its amino group, nucleophilically attacks the carbonyl of the aromatic aldehyde, forming an iminium zwitterion intermediate A. Concurrently, ʟ-proline promotes the generation of the
  • undergoes Michael addition to arylidene intermediate C. The thus formed adduct D is protonated by ʟ-proline and undergoes tautomerization. During the initial experiments to synthesizing methyl and ethyl esters via this four-component reaction, we observed the parallel formation of an undesired cyclic
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Published 09 Feb 2026

Synthesis of diaryl phosphates using phytic acid as a phosphorus source

  • Kazuya Asao,
  • Seika Matsumoto,
  • Haruka Mori,
  • Riku Yoshimura,
  • Takeshi Sasaki,
  • Naoya Hirata,
  • Yasuyuki Hayakawa and
  • Shin-ichi Kawaguchi

Beilstein J. Org. Chem. 2026, 22, 213–223, doi:10.3762/bjoc.22.15

Graphical Abstract
  • -free synthetic methods have been reported for the synthesis of phosphorus compounds (Figure 2A) [35][36][37][38][39][40][41]. Cummins’s group demonstrated that phosphoric acid and condensed phosphoric acid can be reduced using trichlorosilane. The resulting intermediate, the bis(trichlorosilyl
  • phosphoric acid and condensed phosphoric acid into a versatile PO2+ phosphorylation agent, (pyridine)2PO2[OTf]. The intermediate reacts with a variety of nucleophiles, providing a redox-neutral method for the flexible synthesis of P(V) compounds (Figure 2C) [44]. Furthermore, Naganawa’s group recently
  • period for the formation of the phosphate monoester from phosphoric acid; however, an induction period associated with diester formation is observed between the formation of the monoester and the formation of intermediate DPpyP. This difference suggests that the monoester and the diester are formed via
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Published 30 Jan 2026

Base-promoted deacylation of 2-acetyl-2,5-dihydrothiophenes and their oxygen-mediated hydroxylation

  • Vladimir G. Ilkin,
  • Margarita Likhacheva,
  • Igor V. Trushkov,
  • Tetyana V. Beryozkina,
  • Vera S. Berseneva,
  • Vladimir T. Abaev,
  • Wim Dehaen and
  • Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2026, 22, 192–204, doi:10.3762/bjoc.22.13

Graphical Abstract
  • migration in the formed tetrahedral intermediate to afford formate ester; c) hydrolysis of the latter to form phenols [28]. The development of methods for the construction of heterocycles and their modification is an important area of organic synthesis [29]. Although the Dakin oxidation has become a
  • elemental sulfur S6. Probably, the reaction is accompanied by the desulfurization of the oxidized intermediate, which causes the yellow color of the reaction solutions. The proposed mechanism for the developed transformations is depicted in Scheme 6. The reaction of dihydrothiophene 1a with sodium ethoxide
  • led to the intermediate A. Elimination of ethyl/methyl acetate from intermediate A afforded anion B. The latter reacted in ethanolic solution with molecular oxygen [52] with the formation of peroxide anion C. The protonation of anion C with proton sources (residual water or/and solvent or 3a can serve
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Published 28 Jan 2026

Improved synthesis and physicochemical characterization of the selective serotonin 2A receptor agonist 25CN-NBOH

  • Adrian G. Rossebø,
  • Hannah G. Kolberg,
  • Anders E. Tønder,
  • Louise Kjaerulff,
  • Poul Erik Hansen,
  • Karla A. Frydenvang,
  • Jesper Østergaard and
  • Jesper L. Kristensen

Beilstein J. Org. Chem. 2026, 22, 175–184, doi:10.3762/bjoc.22.11

Graphical Abstract
  • The synthesis of 1 starts from commercially available 2,5-dimethoxyphenethylamine (2C-H), which can be transformed into the intermediate 2C-CN, (Figure 1). We have previously reported high yielding 4-step procedure for this process, whereas the yield in the final step in the synthesis of 1 was a
  • modest 65% [12]. In the present work, we found that simply adding 4 Å molecular sieves powder during the formation of the intermediate imine gave a much cleaner reaction and increased the yield of 1·HCl from 2C-CN·HCl to 74%. We suggest that the addition of the molecular sieves facilitates the formation
  • of the required imine intermediate that upon reduction yields the desired product. The free base 1 was purified on normal-phase flash column chromatography, and 1·HCl was subsequently precipitated, providing a white crystalline solid (vide infra). Characterization of 25CN-NBOH·HCl (1·HCl) in the
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Published 22 Jan 2026

A new synthesis of Tyrian purple (6,6’-dibromoindigo) and its corresponding sulfonate salts

  • Holly Helmers,
  • Mark Horton,
  • Julie Concepcion,
  • Jeffrey Bjorklund and
  • Nicholas C. Boaz

Beilstein J. Org. Chem. 2026, 22, 167–174, doi:10.3762/bjoc.22.10

Graphical Abstract
  • purple, several syntheses of 1 have been reported in the literature [5]. As shown in Scheme 1A, a common route to 1 uses 4-bromo-2-nitrotoluene (3) as a key intermediate [5]. We were interested in a safe and cost-efficient synthesis of the major component of Tyrian purple that is amenable to generating
  • similar analogues, using 3 as a key intermediate. Furthermore, we were interested in producing a water-soluble derivative of 1, much like indigo carmine was developed as a water-soluble derivative of indigo. Several syntheses of 3 have been reported, but the most common method involves the selective
  • nitration of p-toluidine (2), followed by a Sandmeyer bromination [5][6][7][8][9]. While such chemistry is effective in smoothly generating 3 in good yield, this process requires the production of and use of a potentially explosive aryldiazonium intermediate [10]. Oxidation of the methyl group in 3 yields 4
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Published 21 Jan 2026

Circumventing Mukaiyama oxidation: selective S–O bond formation via sulfenamide–alcohol coupling

  • Guoling Huang,
  • Huarui Zhu,
  • Shuting Zhou,
  • Wanlin Zheng,
  • Fangpeng Liang,
  • Zhibo Zhao,
  • Yifei Chen and
  • Xunbo Lu

Beilstein J. Org. Chem. 2026, 22, 158–166, doi:10.3762/bjoc.22.9

Graphical Abstract
  • -bromosuccinimide to generate a highly electrophilic sulfilimidoyl bromide intermediate R–S(Br)=N–C(O)R’, along with succinimide. The resulting S(IV)–Br species is then attacked by the alcohol 2, and nucleophilic substitution at sulfur followed by proton transfer furnishes the sulfinimidate ester 3 and HBr. The
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Published 20 Jan 2026

Highly electrophilic, gem- and spiro-activated trichloromethylnitrocyclopropanes: synthesis and structure

  • Ilia A. Pilipenko,
  • Mikhail V. Grigoriev,
  • Olga Yu. Ozerova,
  • Igor A. Litvinov,
  • Darya V. Spiridonova,
  • Aleksander V. Vasilyev and
  • Sergey V. Makarenko

Beilstein J. Org. Chem. 2026, 22, 123–130, doi:10.3762/bjoc.22.5

Graphical Abstract
  • to the bromonitroalkene afford the intermediate anion II, followed by tautomerization and formation of anion IV, which undergoes intramolecular nucleophilic substitution of the bromide along the C-alkylation pathway [37][38][39] (Scheme 6). The trans-configuration of the methine protons of the
  • by BH+ from the side opposite to the –CH(EWG)2. Thus, only diastereomer III is formed. Deprotonation of this intermediate leads to carbanion IV. For further attack by the carbanion center to the carbon atom bonded to bromine, the –C(EWG)2 moiety must hold an anti-periplanar position relative to the
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Published 14 Jan 2026

Total synthesis of natural products based on hydrogenation of aromatic rings

  • Haoxiang Wu and
  • Xiangbing Qi

Beilstein J. Org. Chem. 2026, 22, 88–122, doi:10.3762/bjoc.22.4

Graphical Abstract
  • process relies on the rapid interconversion of the enantiomers in the racemic substrate, which in turn relies on the acid-promoted isomerization between the aromatic indole and the nonaromatic exocyclic enamine intermediate. Very recently, Chen and co-workers reported that using a Mn catalyst with
  • ]. Starting from compounds 77 and 78, Baldwin and co-workers converted them into pyridine derivative 79 in high yield over three steps including a Wittig reaction and tosylation. Subsequent reduction with sodium borohydride furnished the dimer 80 bearing partially reduced pyridine rings. From 80, intermediate
  • , followed by hydrazinolysis to generate alcohol 120. Starting from the common intermediate 120, the total syntheses of renieramycin and lemonomycinone were accomplished through 11 and 13 steps, respectively. Total synthesis to the alkaloids GB13 by Sarpong, 2009 In 2009, Sarpong and co-workers reported a
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Published 07 Jan 2026

Advances in Zr-mediated radical transformations and applications to total synthesis

  • Hiroshige Ogawa and
  • Hugh Nakamura

Beilstein J. Org. Chem. 2026, 22, 71–87, doi:10.3762/bjoc.22.3

Graphical Abstract
  • , Schwartz’s reagent reacts with triethylborane to generate a low-valent zirconium complex 5. This complex abstracts the halogen atom from the alkyl halide, forming alkyl radical 8. The radical then cyclizes onto the olefin, and the resulting radical intermediate undergoes hydrogen atom transfer (HAT) from
  • , demonstrating excellent functional group tolerance. The proposed mechanism is shown in Scheme 2C. Zirconocene dichloride is first reduced by zinc dust to generate ZrII. The resulting low-valent zirconium species reacts with the alkyl iodide to form a metal-centered radical intermediate. This species undergoes
  • its subsequent radical addition to 2-methylene-1,3-dithiane (14) proceeded, affording radical intermediate 15. This radical intermediate rapidly underwent homodimerization to give vic-bis(dithiane) 16. The reaction could be applied to both tertiary and secondary alkyl halides, providing the
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Published 05 Jan 2026

Reactivity umpolung of the cycloheptatriene core in hexa(methoxycarbonyl)cycloheptatriene

  • Dmitry N. Platonov,
  • Alexander Yu. Belyy,
  • Rinat F. Salikov,
  • Kirill S. Erokhin and
  • Yury V. Tomilov

Beilstein J. Org. Chem. 2026, 22, 64–70, doi:10.3762/bjoc.22.2

Graphical Abstract
  • excellent yield, the structure being confirmed using single crystal X-ray analysis (CCDC 2495984). Bromination afforded a mixture of symmetric cycloheptatriene 4b and norcaradiene 6b, while intermediate cycloheptatriene 5b was not even observed. Iodination gave exclusively norcaradiene 6c. Previously
  • isomerization. However, these isomerizations are known to proceed as 1,5-sigmatropic shift [32] as observed in the formation of compounds 8 and 9, whereas the formation of products 4 through this pathway would require at least two consequent shifts. Thus, the absence of any intermediate-shift products along
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Published 05 Jan 2026

Synthesis and applications of alkenyl chlorides (vinyl chlorides): a review

  • Daniel S. Müller

Beilstein J. Org. Chem. 2026, 22, 1–63, doi:10.3762/bjoc.22.1

Graphical Abstract
  • to alkenyl chlorides with phosphorous pentachloride (PCl5): Friedel first reported the reaction of PCl5 with acetophenone (1) in 1868 (Scheme 1A) [45]. Treatment of the resulting intermediate 2 – then presumed to be a gem-dichloride – with aqueous KOH led to the formation of phenylacetylene (3). In
  • dichloro intermediate 5 yielded the corresponding alkenyl chloride 6. In 1913, Faworsky revisited this transformation in an effort to prepare tetramethylallene (7) (Scheme 1C) [47]. However, several attempts to reproduce Henry’s procedure were unsuccessful. Instead, Faworsky isolated the α-chlorinated
  • under the reaction conditions (acetate II). Subsequent addition of HCl to intermediate II generates chloride III, which undergoes elimination to yield the desired product IV. Kodomari and co-workers serendipitously discovered a related reaction in which a large excess of acetyl chloride (8 equivalents
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Published 02 Jan 2026
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