Photomechanochemistry: harnessing mechanical forces to enhance photochemical reactions

• Francesco Mele,
• Ana M. Constantin,
• Andrea Porcheddu,
• Raimondo Maggi,
• Giovanni Maestri,
• Nicola Della Ca’ and
• Luca Capaldo

Beilstein J. Org. Chem. 2025, 21, 458–472, doi:10.3762/bjoc.21.33

• for its high-energy input, automated operation, and reproducibility, making it ideal for larger-scale and more force-intensive reactions. Both LED strips and LED lamps are used as light sources in combination with transparent jars in PMMA, glass, or epoxy resins. It can achieve consistent results but

Emerging trends in the optimization of organic synthesis through high-throughput tools and machine learning

• Pablo Quijano Velasco,
• Kedar Hippalgaonkar and
• Balamurugan Ramalingam

Beilstein J. Org. Chem. 2025, 21, 10–38, doi:10.3762/bjoc.21.3

• resins, laboratories are witnessing a surge in options for efficient high-throughput purification, particularly in chemical synthesis on a modest scale. A change in thinking beyond conventional purification methods presents an opportunity to revolutionize HTE flow platforms. A completely novel design

O,S,Se-containing Biginelli products based on cyclic β-ketosulfone and their postfunctionalization

• Kateryna V. Dil and
• Vitalii A. Palchykov

Beilstein J. Org. Chem. 2024, 20, 2143–2151, doi:10.3762/bjoc.20.184

• ). Results and Discussion Reaction optimization Over the past two decades more than 300 various catalytic systems have been proposed for Biginelli chemistry, e.g., simple inorganic and organic acids, metal salts, metal oxides, ionic liquids, phosphines, nanocatalysts, organocatalysts, ion exchange resins [1

Factors influencing the performance of organocatalysts immobilised on solid supports: A review

• Zsuzsanna Fehér,
• Dóra Richter,
• Gyula Dargó and
• József Kupai

Beilstein J. Org. Chem. 2024, 20, 2129–2142, doi:10.3762/bjoc.20.183

• prolinamide-thiourea organocatalyst onto commercially available resins (JandaJel, polystyrene-divinylbenzene, and ChemMatrix) results in diminished catalytic activity, both in terms of yield and enantiomeric excess values, compared to the homogeneous analogue [117]. On the contrary, Dumesic and co-workers

Synthetic applications of the Cannizzaro reaction

• Bhaskar Chatterjee,
• Dhananjoy Mondal and
• Smritilekha Bera

Beilstein J. Org. Chem. 2024, 20, 1376–1395, doi:10.3762/bjoc.20.120

• . The Cannizzaro reaction also finds extensive industrial use in synthesizing pentaerythritol, a crucial intermediate in manufacturing of alkyd resins and plasticizers [55]. The crossed-Cannizzaro reaction contributes to polyol production for polyester resin synthesis. In the field of fragrance and

Radical chemistry in polymer science: an overview and recent advances

• Zixiao Wang,
• Feichen Cui,
• Yang Sui and
• Jiajun Yan

Beilstein J. Org. Chem. 2023, 19, 1580–1603, doi:10.3762/bjoc.19.116

• . Cook et al. [85] presented the first report of volumetric additive manufacturing-printed thiol–ene resins and showed the potential of the thiol–ene system. In addition to thiol–ene chemistry, radical hydrosilylation was also used to prepare linear, branched, or cross-linked polymers via a step-growth

Linker, loading, and reaction scale influence automated glycan assembly

• Marlene C. S. Dal Colle,
• Manuel G. Ricardo,
• Nives Hribernik,
• José Danglad-Flores,
• Peter H. Seeberger and
• Martina Delbianco

Beilstein J. Org. Chem. 2023, 19, 1015–1020, doi:10.3762/bjoc.19.77

• mostly performed on cross-linked polystyrene resins equipped with photocleavable linkers [3], offering orthogonality to all the synthetic steps of the assembly, while selectively releasing the glycan at the end of the synthesis. In recent years, the implementation of new synthetic strategies [4][5][6][7

• cleavage is probably influenced by glycan structure, solubility, and aggregation tendency [26]. Lastly, purification of the protected glycan upon cleavage could be affected by the presence or absence of a linker. L1 or L2 were conjugated to Merrifield resins with initial loadings of 0.5 mmol/g and 1.0 mmol

• -1,6-linked dimannosides 1 and 2 (Figure 2A) were successful on all resins tested, affording the desired product in complete purity regardless of linker type, loading or reaction scale (Figure 3A, and Figures S2 and S3 in Supporting Information File 1). Isolated yields of 49–59% were obtained in all

Nostochopcerol, a new antibacterial monoacylglycerol from the edible cyanobacterium Nostochopsis lobatus

• Naoya Oku,
• Saki Hayashi,
• Yuji Yamaguchi,
• Hiroyuki Takenaka and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2023, 19, 133–138, doi:10.3762/bjoc.19.13

• reason for the low yield of compound 1 was eventually understood after it was determined to be a monoacylglycerol, which has a surface-active property and should have deteriorated the separation capacity of the chromatographic resins. The molecular formula of compound 1 was established to be C19H34O4

Inline purification in continuous flow synthesis – opportunities and challenges

• Jorge García-Lacuna and
• Marcus Baumann

Beilstein J. Org. Chem. 2022, 18, 1720–1740, doi:10.3762/bjoc.18.182

• heterogeneous fashion. This oftentimes leads to improved green credentials, safety, and sometimes efficiency, especially when it is applied to the downstream process. Commercially available resins, activated charcoal, polymer-supported species that trap spent reagents or side-products as well as related

• /catalyst/byproduct to telescope several reactions before performing the final purification step offline (Scheme 8) [80][81][82][83]. Notable applications of metal scavengers such as QuadraPure® resins involve the removal of leached metals as well as catalytic amounts of homogeneous metal catalysts as

• ). In another case, the authors opt to use stoichiometric quantities of reagents to avoid the use of cartridges, even if the performance is worse, to reduce cost and time [93]. Catch and release strategy An interesting approach regarding the use of resins is their application in catch and release

Electro-conversion of cumene into acetophenone using boron-doped diamond electrodes

• Mana Kitano,
• Tsuyoshi Saitoh,
• Shigeru Nishiyama,
• Yasuaki Einaga and
• Takashi Yamamoto

Beilstein J. Org. Chem. 2022, 18, 1154–1158, doi:10.3762/bjoc.18.119

• -doped diamond electrode; electrosynthesis; oxidation; Introduction Selective oxidation of aromatic alkyl side chains is an important molecular transformation process to obtain various rubbers, resins, fine chemicals, and other industrial products [1][2]: terephthalic acid from p-xylene, cumene

Synthesis of odorants in flow and their applications in perfumery

• Merlin Kleoff,
• Paul Kiler and
• Philipp Heretsch

Beilstein J. Org. Chem. 2022, 18, 754–768, doi:10.3762/bjoc.18.76

• such as the Egyptian around 5000 BC where resins of incense, opoponax, and myrrh were burnt for religious purposes [1]. Today, “the art of perfumery is closely connected to [synthetic] chemistry“, as outlined by Jean-Claude Ellena, the former master perfumer of Hermès [2]. In fact, the development of

• before the aldol condensation is initiated at 240 °C. While at lower temperatures, the aldol condensation proceeded incompletely, increasing the temperature to 250 °C lead to clogging of the reactor probably due to formation of phenolic resins as byproducts. In contrast, when the reaction is performed at

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

• Guido Gambacorta,
• James S. Sharley and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

• (60–70%) [119]. By using ion-exchange resins such as Amberlyst® A26 (OH form) as a heterogeneous base in a fixed-bed reactor, the α,β-unsaturated compound 80 was obtained and with a stable performance over more than 15 hours of continuous operation (Scheme 14). In 2019, the group of Kobayashi

Synthetic accesses to biguanide compounds

• Oleksandr Grytsai,
• Cyril Ronco and
• Rachid Benhida

Beilstein J. Org. Chem. 2021, 17, 1001–1040, doi:10.3762/bjoc.17.82

• production of biodiesel [5][80], intermediates for triazine synthesis [48], etc. Some derivatives were grafted onto polystyrene resins for catalytic uses [5]. Various solvents and temperatures were used such as hot DMF [5], neat [79], toluene or hexane at 25–100 °C [79]. Generally, higher temperatures seem

Valorisation of plastic waste via metal-catalysed depolymerisation

• Francesca Liguori,
• Carmen Moreno-Marrodán and
• Pierluigi Barbaro

Beilstein J. Org. Chem. 2021, 17, 589–621, doi:10.3762/bjoc.17.53

• role of butoxide was postulated to be the activation of the heterogeneous splitting of dihydrogen. BDM is an important building block for the production of resins and polyesters other than PET [186][187]. Analogously, a similar Milstein-type ruthenium–PNN complex, generated in situ by treatment of the

• , polyurethanes, polyisocyanurates and resins [43]. Among the various glycols, EG is the most popular, resulting in the formation of BHET, formally through a (reversible) transesterification reaction (Scheme 5) [198]. Drawbacks of this method are the difficulty of purification of BHET, the need of an excess of EG

Coupling biocatalysis with high-energy flow reactions for the synthesis of carbamates and β-amino acid derivatives

• Alexander Leslie,
• Thomas S. Moody,
• Megan Smyth,
• Scott Wharry and
• Marcus Baumann

Beilstein J. Org. Chem. 2021, 17, 379–384, doi:10.3762/bjoc.17.33

• equiv) resins packed into an Omnifit glass column (10 cm length, 10 mm i.d., rt). This approach facilitated the removal of triethylamine, residual acid substrate, and diphenylphosphonic acid (generated from DPPA) and rendered a solution of the carbamate product containing only unreacted benzyl alcohol

Synthesis of imidazo[1,5-a]pyridines via cyclocondensation of 2-(aminomethyl)pyridines with electrophilically activated nitroalkanes

• Dmitrii A. Aksenov,
• Nikolai A. Arutiunov,
• Vladimir V. Maliuga,
• Alexander V. Aksenov and
• Michael Rubin

Beilstein J. Org. Chem. 2020, 16, 2903–2910, doi:10.3762/bjoc.16.239

• , the yield of 16a improved to 62% (Table 1, entry 8), while at 160 °C, it reached 77% (Table 1, entry 9). It should be pointed out that the reported yield of 77% is the isolated yield given complete conversion, with no detected side products aside from easily removable polymeric resins. With optimized

Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases

• Julia N. Artsemyeva,
• Ekaterina A. Remeeva,
• Tatiana N. Buravskaya,
• Irina D. Konstantinova,
• Roman S. Esipov,
• Anatoly I. Miroshnikov,
• Natalia M. Litvinko and
• Igor A. Mikhailopulo

Beilstein J. Org. Chem. 2020, 16, 2607–2622, doi:10.3762/bjoc.16.212

• Shemyakin and Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya 16/10, 117997 GSP-7, Moscow B-437, Russian Federation 10.3762/bjoc.16.212 Abstract In the present work, we suggested anion exchange resins in the phosphate form as a source of phosphate, one of the

• were tested in the synthesis of nelarabine, kinetin riboside, and cladribine with good to excellent yields (52–93%). Keywords: anion exchange resins; N6-benzyladenosine; cladribine; enzymatic glycosylation; kinetin riboside; nelarabine; α-ᴅ-pentofuranose-1-phosphates; phosphorolysis of nucleosides

• MeCN; 99.0% purity according to HPLC; for NMR data, see Supporting Information File 1, SI-1, SI-2 and SI-4). The capacity of the anion exchange resins to bind PF-1Pi As noted above, when studying Ara-U phosphorolysis catalyzed by E. coli UP in the presence of Dowex-nPi, we found that (1) about 10% of

Synergy between supported ionic liquid-like phases and immobilized palladium N-heterocyclic carbene–phosphine complexes for the Negishi reaction under flow conditions

• Edgar Peris,
• Raúl Porcar,
• María Macia,
• Jesús Alcázar,
• Eduardo García-Verdugo and
• Santiago V. Luis

Beilstein J. Org. Chem. 2020, 16, 1924–1935, doi:10.3762/bjoc.16.159

• obtained for AuNPs-SILLPs indicated that for the macroporous resins the NP size decreased when the size of the aliphatic residue of the imidazolium units increased with decyl N-substitution leading to smaller particle sizes [39]. The analysis of the polymeric samples revealed similar trends for the case of

Nonenzymatic synthesis of anomerically pure, mannosyl-based molecular probes for scramblase identification studies

• Giovanni Picca,
• Markus Probst,
• Simon M. Langenegger,
• Oleg Khorev,
• Peter Bütikofer,
• Anant K. Menon and
• Robert Häner

Beilstein J. Org. Chem. 2020, 16, 1732–1739, doi:10.3762/bjoc.16.145

• moiety for photocrosslinking to MPD-recognizing proteins. The presence of an additional propargyl group provides a way to further derivatize the probe with biotin azide via click-type chemistry [16] for the isolation of protein–lipid adducts using streptavidin resins [10]. To synthesize such molecular

One-pot synthesis of isosorbide from cellulose or lignocellulosic biomass: a challenge?

• Isaline Bonnin,
• Raphaël Mereau,
• Thierry Tassaing and
• Karine De Oliveira Vigier

Beilstein J. Org. Chem. 2020, 16, 1713–1721, doi:10.3762/bjoc.16.143

• -isosorbide) terephthalate, can replace polyethylene terephthalate (PET) [7]. In the production of polycarbonate and epoxy resins, the physicochemical properties of isosorbide allow the replacement of bisphenol A by this bio-based molecule [8][9]. At an industrial level, isosorbide is produced from the double

• Solid acid catalysts such as ion exchange resins exhibiting sulfonic groups on their external surface resembling to some extent p-toluenesulfonic acid (p-TSA) can be used in combination with supported metal catalyst (Scheme 6). Yamaguchi et al. used a combination of Ru/C and Pt/C with Amberlyst 70, an

Heterogeneous photocatalysis in flow chemical reactors

• Christopher G. Thomson,
• Ai-Lan Lee and
• Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

• still trapped in the resins after the extraction, which led to a dramatic loss in photosensitisation efficiency over multiple recycles as it was progressively washed out. The flow-purified resins displayed no loss of efficiency over the recycles, indicating the flow purification had effectively removed

• the homogeneous photocatalyst. The flow synthesis also prevented the formation of a chlorinated byproduct identified on the batch resins as an intermediate, and purification could be applied to wash out reactants from the first step of the one-pot synthesis, a potentially useful synthetic advantage of

• postsynthetic modifications in flow [63]. Poliakoff, George, and co-workers reported a porphyrin photosensitiser ionically immobilised to sulphonate-cross-linked ion exchange polystyrene resins (amberlyst-15) for the synthesis of artemisinin (49). This resulted in a bifunctional material, which acts as a HPCat

Synthetic terpenoids in the world of fragrances: Iso E Super^® is the showcase

• Alexey Stepanyuk and
• Andreas Kirschning

Beilstein J. Org. Chem. 2019, 15, 2590–2602, doi:10.3762/bjoc.15.252

• of years dating back well before biblical times [2][3]. Plants and resins served as source for perfumes after alcoholic extraction. These extracts were not only used as fragrances but also as medicine (aqua mirabilis), aphrodisiac and elixir of life (aquavitae). In 1882 'Fougere Royale' was created

Identification of optimal fluorescent probes for G-quadruplex nucleic acids through systematic exploration of mono- and distyryl dye libraries

• Xiao Xie,
• Michela Zuffo,
• Marie-Paule Teulade-Fichou and
• Anton Granzhan

Beilstein J. Org. Chem. 2019, 15, 1872–1889, doi:10.3762/bjoc.15.183

• in the high-ionic-strength aqueous buffer required for native G4 structures was insufficient. In these cases, ion exchange to bromide (1b, 1ð, 1u, 6a, 7b, 7n) or chloride (1d, 1k–1q, 1t, 1w, 7ð, as well as 8a–12a and 14a–16a) was performed using ion-exchange resins (cf. Supporting Information File 1

Organometallic vs organic photoredox catalysts for photocuring reactions in the visible region

• Aude-Héloise Bonardi,
• Frédéric Dumur,
• Guillaume Noirbent,
• Jacques Lalevée and
• Didier Gigmes

Beilstein J. Org. Chem. 2018, 14, 3025–3046, doi:10.3762/bjoc.14.282

• ) and the low content required. All these works on PC pave the way for highly reactive photosensitive systems that can be used for high tech applications: functional coatings, smart materials, new 3D printing resins, preparation of composites. Other development of PC can be expected in near future

Synthesis of a tyrosinase inhibitor by consecutive ethenolysis and cross-metathesis of crude cashew nutshell liquid

• Jacqueline Pollini,
• Valentina Bragoni and
• Lukas J. Gooßen

Beilstein J. Org. Chem. 2018, 14, 2737–2744, doi:10.3762/bjoc.14.252

• properties and industrial applications, for instance in surfactants, plasticizers, resins, soft materials and diverse medical applications [7]. Isolated via cold-press or solvent extraction processes, it contains predominantly anacardic acid (1). Upon distillation or any other thermal treatment, anacardic

• ][10]. These include aromatic amines as polymers [11][12], cardanol-based phosphates as modifiers for epoxy resins [13], cardanol grafted natural rubber as rubber plasticizers [14], amine-based surfactants [15] and phenol/cardanol-formaldehyde based adhesives [16]. The chemical valorization of