Synthesis, structure and π-expansion of tris(4,5-dehydro-2,3:6,7-dibenzotropone)

• Yongming Xiong,
• Xue Lin Ma,
• Shilong Su and
• Qian Miao

Beilstein J. Org. Chem. 2025, 21, 1–7, doi:10.3762/bjoc.21.1

• . This corresponds to a molecular formula of C119H122O9, which is in agreement with the fully fused product 11 in its protonated form. Unfortunately, clean 1H and 13C NMR spectra of this product could not be obtained to allow full characterization of this product. Efforts to increase the yield of 11

Synthesis, characterization, and photophysical properties of novel 9‑phenyl-9-phosphafluorene oxide derivatives

• Shuxian Qiu,
• Duan Dong,
• Jiahui Li,
• Huiting Wen,
• Jinpeng Li,
• Yu Yang,
• Shengxian Zhai and
• Xingyuan Gao

Beilstein J. Org. Chem. 2024, 20, 3299–3305, doi:10.3762/bjoc.20.274

• available 2-bromo-4-fluoro-1-nitrobenzene, featuring a noble-metal-free system, mild reaction conditions, and a good yield, especially for the final Cs2CO3-facilitated nucleophilic substitution (77–91% yield). The characterization data obtained from IR and NMR spectroscopy (1H, 13C, 19F, and 31P) as well as

Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade

• Merve Yence,
• Dilgam Ahmadli,
• Damla Surmeli,
• Umut Mert Karacaoğlu,
• Sujit Pal and
• Yunus Emre Türkmen

Beilstein J. Org. Chem. 2024, 20, 3290–3298, doi:10.3762/bjoc.20.273

• , characterization data, and copies of 1H and 13C{1H} NMR spectra. Acknowledgements The data presented in this article are partially taken from the M.Sc. theses of Merve Yence (Bilkent University, 2019) and Dilgam Ahmadli (Bilkent University, 2021). Funding Financial support for some parts of this work from the

Giese-type alkylation of dehydroalanine derivatives via silane-mediated alkyl bromide activation

• Perry van der Heide,
• Michele Retini,
• Fabiola Fanini,
• Giovanni Piersanti,
• Francesco Secci,
• Daniele Mazzarella,
• Timothy Noël and
• Alberto Luridiana

Beilstein J. Org. Chem. 2024, 20, 3274–3280, doi:10.3762/bjoc.20.271

• nm, 25 °C, overnight. The yield of 3 was calculated by 1H NMR with 1,1,2-trichloroethene as external standard. Supporting Information Supporting Information File 52: 1H NMR, 13C NMR, and HRMS spectra of all the synthesized compounds. Acknowledgements We are grateful to University Research Services

Efficient synthesis of fluorinated triphenylenes with enhanced arene–perfluoroarene interactions in columnar mesophases

• Yang Chen,
• Jiao He,
• Hang Lin,
• Hai-Feng Wang,
• Ping Hu,
• Bi-Qin Wang,
• Ke-Qing Zhao and
• Bertrand Donnio

Beilstein J. Org. Chem. 2024, 20, 3263–3273, doi:10.3762/bjoc.20.270

• ) was synthesized via consecutive Suzuki coupling and Scholl reaction in a total yield of 77%. The synthesis, molecular structures, nomenclature, and synthetic yields of all compounds are shown in general Scheme 1. All prepared molecules were fully characterized by NMR (1H, 19F and 13C), HRMS, and CHN

• '-hexafluoro-6,6',7,7',10,10',11,11'-octakisalkoxy-2,2'-bitriphenylene dimers (G55, G66 and G48). Mesophases’ parameters. Supporting Information Synthesis (Schemes S1–S3) and characterization, 1H, 13C, and 19F NMR (Figures S1–S21), HRMS (Figures S22–S32), EA, single crystal X-ray structures (Figures S33, S34

Intramolecular C–H arylation of pyridine derivatives with a palladium catalyst for the synthesis of multiply fused heteroaromatic compounds

• Yuki Nakanishi,
• Shoichi Sugita,
• Kentaro Okano and
• Atsunori Mori

Beilstein J. Org. Chem. 2024, 20, 3256–3262, doi:10.3762/bjoc.20.269

• , J = 8.4, 8.0, 1.2 Hz, 1H), 7.37 (d, J = 8.4 Hz, 1H), 7.30 (dd, J = 8.0, 7.6 Hz, 1H), 4.40 (dd, J = 8.0, 7.6 Hz, 2H), 1.76–1.88 (m, 2H), 1.44–1.56 (m, 2H), 1.18–1.42 (m, 8H), 0.86 (t, J = 6.8 Hz, 3H); 13C{1H} NMR (CDCl3) δ 160.1, 148.4, 142.0, 136.7, 131.1, 130.5, 130.2, 130.1, 129.1, 128.7, 127.7

• . Supporting Information File 48: Additional experimental details and copies of 1H and 13C{1H} NMR spectra. Acknowledgements We thank Professor Shigeki Mori and Ms. Rimi Konishi (Ehime University) for the X-ray crystallographic analysis.

Ceratinadin G, a new psammaplysin derivative possessing a cyano group from a sponge of the genus Pseudoceratina

• Shin-ichiro Kurimoto,
• Kouta Inoue,
• Taito Ohno and
• Takaaki Kubota

Beilstein J. Org. Chem. 2024, 20, 3215–3220, doi:10.3762/bjoc.20.267

• existence of a substituted benzenoid chromophore was suggested by the UV absorption maximum at 258 nm. The presence of hydroxy and/or amino groups and a carbonyl group was indicated by IR absorptions at 3337 cm−1 and 1671 cm−1, respectively. The analysis of the HSQC spectrum, along with the 1H and 13C NMR

• (partial structures a and b, respectively, in Figure 2), which were characteristic of psammaplysins, in ceratinadin G (1) was suggested by comparison of its 1H and 13C NMR data with those of known psammaplysin derivatives such as psammaplysins A and F (2) [4][5][6][10][11][12]. HMBC correlations (H-1/C-2

• 116.9) and the molecular formula of compound 1, it was inferred that a cyano group is attached to C-22. The 13C NMR chemical shifts of C-22 and C-23 closely matched those of the corresponding carbons in known synthetic compounds with an aminoacetonitrile moiety, further supporting the presence of a

Discovery of ianthelliformisamines D–G from the sponge Suberea ianthelliformis and the total synthesis of ianthelliformisamine D

• Sasha Hayes,
• Yaoying Lu,
• Bernd H. A. Rehm and
• Rohan A. Davis

Beilstein J. Org. Chem. 2024, 20, 3205–3214, doi:10.3762/bjoc.20.266

• protons indicating the presence of a symmetrical aromatic moiety, were observed. The 13C NMR (Table 1) spectrum of 4 showed two carbonyls (δC 164.4, 173.9), with the carbonyl at δC 164.4 readily assigned to an acrylamide group, which is present in all previously published ianthelliformisamine molecules [7

• ]. The 13C NMR (Table 1) data of 5 displayed six aliphatic carbons (δC 35.9, 26.1, 44.8, 46.3, 21.1, 30.4) and two carbonyl signals (δC 164.9, 173.6). Similarly to the other ianthelliformisamines, the aromatic (δC 131.6) and olefin (δC 124.5, 135.2) carbons were observed [7]. COSY correlations associated

• carbon signal. Although a downfield exchangeable CO2H proton was not observed in the 1H NMR spectrum of 5, a carboxylic acid moiety was assigned based on the 13C NMR shift value (δC 173.6) [17], and analysis of the HRESIMS ion at m/z 477.0022 [M + H]+, which confirmed the molecular formula to be

Multicomponent reactions driving the discovery and optimization of agents targeting central nervous system pathologies

• Lucía Campos-Prieto,
• Aitor García-Rey,
• Eddy Sotelo and
• Ana Mallo-Abreu

Beilstein J. Org. Chem. 2024, 20, 3151–3173, doi:10.3762/bjoc.20.261

• compounds with high yields (84–92%). The three most promising compounds of the library (13a, 13b, and 13c) were selected for further detailed characterization. In vitro evaluation was performed employing a high-performance liquid chromatography (HPLC)-based methodology, using the fluorogenic histone

Synthesis of the 1,5-disubstituted tetrazole-methanesulfonylindole hybrid system via high-order multicomponent reaction

• Cesia M. Aguilar-Morales,
• América A. Frías-López,
• Nadia V. Emilio-Velázquez,
• Alejandro Islas-Jácome,
• Angelica Judith Granados-López,
• Jorge Gustavo Araujo-Huitrado,
• Yamilé López-Hernández,
• Hiram Hernández-López,
• Luis Chacón-García,
• Jesús Adrián López and
• Carlos J. Cortés-García

Beilstein J. Org. Chem. 2024, 20, 3077–3084, doi:10.3762/bjoc.20.256

• and resource optimization. In addition, all the target compounds were fully characterized using 1H and 13C NMR spectroscopy and HRMS. It is important to mention that this protocol cannot be considered a true one-pot synthesis, as it requires a solvent exchange between reaction steps (e.g., from

Extension of the π-system of monoaryl-substituted norbornadienes with acetylene bridges: influence on the photochemical conversion and storage of light energy

• Robin Schulte,
• Dustin Schade,
• Thomas Paululat,
• Till J. B. Zähringer,
• Christoph Kerzig and
• Heiko Ihmels

Beilstein J. Org. Chem. 2024, 20, 3061–3068, doi:10.3762/bjoc.20.254

• because by-products interfered with the chromatographic separation; however, these yields are similar to the ones reported for resembling norbornadienes [34][37]. The novel compounds 1h–l,n were identified and fully characterized by NMR spectroscopy (1H, 13C, COSY, HSQC, HMBC), melting point, and

• elemental analysis. All products showed the characteristic 1H NMR spectroscopic signals of norbornadienes, in particular two signals at ca. 2.10 ppm and 2.20 ppm (7-CH2) and two broad singlets between 3 and 4 ppm (bridgehead 1- and 4-CH). In addition, typical 13C NMR shifts of the aryl-substituted

Tunable full-color dual-state (solution and solid) emission of push–pull molecules containing the 1-pyrindane moiety

• Anastasia I. Ershova,
• Sergey V. Fedoseev,
• Konstantin V. Lipin,
• Mikhail Yu. Ievlev,
• Oleg E. Nasakin and
• Oleg V. Ershov

Beilstein J. Org. Chem. 2024, 20, 3016–3025, doi:10.3762/bjoc.20.251

• and compound characterization data, solvatochromic studies for compound 1с, titration data, and 1H and 13C NMR spectra for compounds 1a–i. Funding This work was performed within the framework of the state task of the Ministry of Science and Higher Education of the Russian Federation (project no. FEGR

Synthesis of fluorinated acid-functionalized, electron-rich nickel porphyrins

• Mike Brockmann,
• Jonas Lobbel,
• Lara Unterriker and
• Rainer Herges

Beilstein J. Org. Chem. 2024, 20, 2954–2958, doi:10.3762/bjoc.20.248

• Information File 42: Experimental procedures, characterization data of all products, and copies of 1H, 13C, and 19F NMR spectra. Acknowledgements We thank Dr. Claus Bier for the help with the HPLC–ESIMS measurements.

gem-Difluorovinyl and trifluorovinyl Michael acceptors in the synthesis of α,β-unsaturated fluorinated and nonfluorinated amides

• Monika Bilska-Markowska,
• Marcin Kaźmierczak,
• Wojciech Jankowski and
• Marcin Hoffmann

Beilstein J. Org. Chem. 2024, 20, 2946–2953, doi:10.3762/bjoc.20.247

• experimental procedures, DFT calculations, characterization data, and copies of 1H, 13C, 19F NMR and 1H−13C HSQC spectra. Acknowledgements The calculations were performed in the Poznan Supercomputing and Networking Center.

The charge transport properties of dicyanomethylene-functionalised violanthrone derivatives

• Sondos A. J. Almahmoud,
• Joseph Cameron,
• Dylan Wilkinson,
• Michele Cariello,
• Claire Wilson,
• Alan A. Wiles,
• Peter J. Skabara and
• Graeme Cooke

Beilstein J. Org. Chem. 2024, 20, 2921–2930, doi:10.3762/bjoc.20.244

• solid (440 mg, 60%). 1H NMR (400 MHz, CDCl3) δ 8.79 (d, J = 8.0 Hz, 2H), 8.65 (d, J = 8.1 Hz, 2H), 8.56 (d, J = 7.6 Hz, 2H), 8.40 (d, J = 7.8 Hz, 2H), 8.30 (s, 2H), 7.82 (t, J = 7.6 Hz, 2H), 7.62 (t, J = 7.4 Hz, 2H), 4.05 (m, 4H), 1.77 (m, 2H), 1.38 (m, 16H), 0.93–0.51 (m, 12H); 13C NMR (100 MHz, CDCl3

• (br, 4H), 1.94–1.80 (m, 4H), 1.34 (d, J = 90.2 Hz, 20H), 0.82 (d, J = 6.9 Hz, 6H); 13C NMR (100 MHz, CDCl3) δ 183.2, 156.3, 135.6, 134.5, 133.2, 131.0, 129.4, 128.6, 128.3, 127.7, 127.5, 127.1, 123.6, 123.2, 122.7, 117.2, 113.5, 69.8, 31.9, 29.9, 29.6, 29.5, 26.2, 22.8, 14.2; HRESIMS (m/z): [M + Na

• Hz, 2H), 8.57 (d, J = 7.7 Hz, 2H), 8.39 (d, J = 8.0 Hz, 2H), 8.30 (s, 2H), 7.81 (t, J = 7.4 Hz, 2H), 7.62 (t, J = 7.6 Hz, 2H), 4.26 (s, 4H), 1.92–1.72 (m, 4H), 1.55–1.02 (m, 36H), 0.86 (t, J = 6.8 Hz, 6H); 13C NMR (100 MHz, CDCl3) δ 183.2, 156.4, 135.6, 134.5, 133.2, 131.1, 129.5, 128.6, 128.3, 127.8

Synthesis of pyrrole-fused dibenzoxazepine/dibenzothiazepine/triazolobenzodiazepine derivatives via isocyanide-based multicomponent reactions

• Marzieh Norouzi,
• Mohammad Taghi Nazeri,
• Ahmad Shaabani and
• Behrouz Notash

Beilstein J. Org. Chem. 2024, 20, 2870–2882, doi:10.3762/bjoc.20.241

• product compared to the substitution of phenyl (Scheme 4, 6c). Furthermore, n-butyl isocyanide was used to increase the variety of products and the n-butyl-substituted products 6f–h were obtained with 72–78% yield . All the products were characterized by 1H NMR, 13C NMR, and infrared spectroscopy, and

• . The signal at δ = 3.42 is the NH group. All the protons of the aromatic rings are located from δ = 7.10 to 7.99. In its 13C NMR spectrum, all of the carbon signals appear at δ = 158.3, 152.5, 134.7, 134.2, 133.9, 133.2, 130.8, 130.4, 129.2, 129.1, 129.0 128.9, 128.4, 127.4, 125.8, 122.6, 121.1, 120.6

• δ = 4.65 and δ = 5.84 ppm corresponding to hydrogen I and hydrogen II. Remarkably, at higher temperatures (85 °C), the rapid inversion of the seven-membered ring results in it being observed as a single structure on the 1H NMR time scale (see Figure 3, spectrum F) [19][47][48]. Furthermore, 13C NMR

Synthesis of tricarbonylated propargylamine and conversion to 2,5-disubstituted oxazole-4-carboxylates

• Kento Iwai,
• Akari Hikasa,
• Kotaro Yoshioka,
• Shinki Tani,
• Kazuto Umezu and
• Nagatoshi Nishiwaki

Beilstein J. Org. Chem. 2024, 20, 2827–2833, doi:10.3762/bjoc.20.238

• . Ltd. and purified by distillation. 1H and 13C{1H} NMR spectra were recorded on a JEOL JMN-ECZ400S spectrometer (400 MHz and 100 MHz, respectively) using TMS as internal standard. The assignments of the 13C{1H} NMR signals were reaffirmed by DEPT experiments. IR spectra were recorded with a JASCO FT/IR

• MHz, CDCl3, δ) 7.78 (d, J = 8.0 Hz, 2H), 7.65 (br s, 1H), 7.48 (d, J = 8.0 Hz, 2H), 7.32–7.25 (m, 5H), 4.37 (q, J = 7.2 Hz, 4H), 2.40 (s, 3H), 1.35 (t, J = 7.2 Hz, 6H); 13C{1H} NMR (100 MHz, CDCl3, δ) 165.6 (C), 165.3 (C), 142.8 (C), 130.2 (C), 129.4 (CH), 128.9 (CH), 128.2 (CH), 127.5 (CH), 122.0 (C

• , 92.2 mg, 0.29 mmol, 82% yield) as colorless oil. 1H NMR (400 MHz, CDCl3, δ) 7.88 (d, J = 8.4 Hz, 2H), 7.35–7.22 (m, 7H), 4.45 (s, 2H), 4.42 (q, J = 7.2 Hz, 2H), 2.39 (s, 3H), 1.40 (t, J = 7.2 Hz, 3H); 13C{1H} NMR (100 MHz, CDCl3, δ) 162.0 (C), 160.7 (C), 157.6 (C), 141.8 (C), 136.4 (C), 129.4 (CH

Synthesis and antimycotic activity of new derivatives of imidazo[1,2-a]pyrimidines

• Dmitriy Yu. Vandyshev,
• Daria A. Mangusheva,
• Khidmet S. Shikhaliev,
• Kirill A. Scherbakov,
• Oleg N. Burov,
• Alexander D. Zagrebaev,
• Tatiana N. Khmelevskaya,
• Alexey S. Trenin and
• Fedor I. Zubkov

Beilstein J. Org. Chem. 2024, 20, 2806–2817, doi:10.3762/bjoc.20.236

• imidazole nucleophilic center not involved in the first step. This process leads to the formation of alternative final products: imidazo[1,2-a]imidazoles 10 and 12, imidazo[1,5-a]pyrimidines 4, 5, 11 and 14, and imidazo[1,2-a]diazines 13 and 15. The analysis of the spectral data (1H and 13C NMR, 2D NMR

• unambiguous assignment of the signals for the methine and methylene groups of compounds 4 and 5 was carried out based on the correlations found in the NOESY 1H,1H and HMBC 1H,13C spectra. As an example, the key correlation interactions for compounds 4d and 5d are depicted in Figure 3. Thus, in the NOESY

C–C Coupling in sterically demanding porphyrin environments

• Liam Cribbin,
• Brendan Twamley,
• Nicolae Buga,
• John E. O’ Brien,
• Raphael Bühler,
• Roland A. Fischer and
• Mathias O. Senge

Beilstein J. Org. Chem. 2024, 20, 2784–2798, doi:10.3762/bjoc.20.234

• the existence of this structure in solution was obtained from VT-NMR studies (Figure S51 and Figure S52 in Supporting Information File 1), with asymmetry observed in the β-ethyl CH3 resonances δH = 0.58 and 0.73 ppm and peak broadening in both the aromatic region and the {1H}13C NMR spectra

• borylation of porphyrin 13 to yield 46. Mean geometrical parameters of OET-meta/para-ArylPP and out-of-plane and in-plane distortion magnitudes. Supporting Information Supporting Information File 9: Experimental methods, synthetic procedures, 1H, 11B and 13C NMR, VT-NMR, UV–vis, IR, HRMS (m/z)-APCI and HRMS

Access to optically active tetrafluoroethylenated amines based on [1,3]-proton shift reaction

• Yuta Kabumoto,
• Eiichiro Yoshimoto,
• Bing Xiaohuan,
• Masato Morita,
• Motohiro Yasui,
• Shigeyuki Yamada and
• Tsutomu Konno

Beilstein J. Org. Chem. 2024, 20, 2776–2783, doi:10.3762/bjoc.20.233

• reaction mechanism. Investigation of the reaction conditions. Supporting Information Supporting Information File 3: Full experimental details, 1H, 13C, 19F NMR spectra of 16a–g and 23a–g, and HPLC charts of racemic as well as chiral compounds 23a–g. Supporting Information File 4: Crystallographic

Copper-catalyzed yne-allylic substitutions: concept and recent developments

• Shuang Yang and
• Xinqiang Fang

Beilstein J. Org. Chem. 2024, 20, 2739–2775, doi:10.3762/bjoc.20.232

• shuttling (Scheme 53, 51a–k). Furthermore, they established a Cu-catalyzed asymmetric multicomponent reaction for yne-allylic substitution, seamlessly integrating 13C-labeled CO2 into enantiomerically pure products (Scheme 54, 51a, 51c, 51f, 51g). This methodology enabled the synthesis of diverse, high

Synthesis of spiroindolenines through a one-pot multistep process mediated by visible light

• Francesco Gambuti,
• Jacopo Pizzorno,
• Chiara Lambruschini,
• Renata Riva and
• Lisa Moni

Beilstein J. Org. Chem. 2024, 20, 2722–2731, doi:10.3762/bjoc.20.230

• laboratory, and the results will be reported in due course. Experimental General methods 1H, 13C and 19F NMR spectra were recorded on a JEOL 400 spectrometer (at 400 MHz, 101 MHz and 376 MHz, respectively). Unless otherwise stated, NMR spectra were recorded using residual solvent as the internal standard; 1H

• NMR: TMS = 0.00; (CD3)2SO = 2.50; and 13C NMR: CDCl3 = 77.16; (CD3)2SO = 39.52. Data for 1H NMR spectra are reported as follows: chemical shift (δ ppm), multiplicity, coupling constants (Hz) and integration. Data for 13C NMR spectra are reported in terms of chemical shift (δ ppm). Interpretation of

• without further purification. Graphene oxide (GO) was purchased from Graphenea. All products were characterized by 1H,13C, 19F (when fluorine is present) NMR, IR and HRMS. General procedure for the one-pot synthesis of spiro[indole-isoquinoline] 3a: A solution of N-phenyltetrahydroisoquinoline (1 equiv

Synthesis of benzo[f]quinazoline-1,3(2H,4H)-diones

• Ruben Manuel Figueira de Abreu,
• Peter Ehlers and
• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 2708–2719, doi:10.3762/bjoc.20.228

• , bathochromically shifted absorption and emission spectra with elevated extinction coefficients and quantum yields up to 71%. Further studies will be directed to the synthesis to polycyclic, π-conjugated uracil derivatives. Experimental General information Nuclear magnetic resonance spectra (1H/13C/19F NMR) were

• –7.41 (m, 2H), 7.41–7.36 (m, 2H), 7.34–7.29 (m, 2H), 7.24–7.21 (m, 2H), 3.71 (s, 3H), 3.45 (s, 3H); 13C {1H} NMR (126 MHz, chloroform-d) δ 162.1, 151.6, 134.3, 133.2, 131.9, 130.9, 130.5, 128.7, 128.3, 128.0, 120.7, 119.0, 104.2, 81.0, 34.6, 28.7; EIMS (70 eV) m/z (%): 315 (100, M+), 258 (26), 230 (67

• ) δ −113.3, −106.3; 13C {1H} NMR (126 MHz, chloroform-d) δ 163.9 (d, J = 253.7 Hz), 162.7 (d, J = 247.8 Hz), 162.0, 151.5, 134.3, 134.1 (d, J = 9.0 Hz), 132.8 (d, J = 8.2 Hz), 129.1 (d, J = 3.3 Hz), 117.9, 116.6 (d, J = 3.6 Hz), 116.4 (d, J = 22.4 Hz), 115.1 (d, J = 21.6 Hz), 103.3, 80.7, 34.7, 28.7

Synthesis of fluoroalkenes and fluoroenynes via cross-coupling reactions using novel multihalogenated vinyl ethers

• Yukiko Karuo,
• Keita Hirata,
• Atsushi Tarui,
• Kazuyuki Sato,
• Kentaro Kawai and
• Masaaki Omote

Beilstein J. Org. Chem. 2024, 20, 2691–2703, doi:10.3762/bjoc.20.226

• and 3 as new fluorine-containing building blocks. Experimental General information 1H NMR, 19F NMR, and 13C NMR spectra were recorded on JEOL ECZ 400S spectrometers. Chemical shifts of 1H NMR are reported in ppm from tetramethylsilane (TMS) as an internal standard. Chemical shifts of 13C NMR are

• purified by column chromatography and preparative TLC (hexane only), and obtained in 96% yield (122.0 mg) as a pale yellow oil; 1H NMR (400 MHz, CDCl3) δ 7.04–7.22 (m, 2H), 7.26–7.50 (m, 6H), 7.55–7.69 (m, 2H); 13C NMR (100 MHz, CDCl3) δ 101.4 (d, J = 30.9 Hz), 102.5 (d, J = 48.0 Hz), 116.5 (d, J = 3.8 Hz

• , J = 8.0 Hz, 2H), 7.07–7.15 (m, 2H), 7.16–7.23 (m, 1H) , 7.33–7.42 (m, 1H); 13C NMR (100 MHz, CDCl3) δ −0.36, −0.26, 85.2 (d, J = 44.8 Hz), 85.6 (d, J = 53.3 Hz), 94.5 (d, J = 47.8 Hz), 94.6 (d, J = 43.5 Hz), 103.7 (d, J = 63.4 Hz), 103.8 (d, J = 66.3 Hz), 117.2, 117.3, 125.2, 125.3, 130.0, 130.1

Transition-metal-free decarbonylation–oxidation of 3-arylbenzofuran-2(3H)-ones: access to 2-hydroxybenzophenones

• Bhaskar B. Dhotare,
• Seema V. Kanojia,
• Chahna K. Sakhiya,
• Amey Wadawale and
• Dibakar Goswami

Beilstein J. Org. Chem. 2024, 20, 2655–2667, doi:10.3762/bjoc.20.223

• characterized using 1H NMR, 13C NMR, FTIR spectroscopy, and elemental analysis. Next, in a model experiment, we carried out the decarbonylation–oxidation reaction of 5-methyl-3-phenylbenzofuran-2(3H)-one (3ba) using different bases in different solvents (Table 1) under open atmospheric conditions. In the

• over anhydrous Na2SO4. FTIR spectra were recorded as films with a Bruker Tensor II spectrophotometer. The 1H and 13C NMR spectra were recorded with a Varian 500 MHz NMR spectrometer, and were processed using Bruker TOPSPIN software. Melting points (mp) were measured on a Büchi B-540 apparatus. X-ray

• File 10: Characterization data of compounds 3aa–ma, 4aa–ma, and 5. 1H and 13C NMR spectra of 3aa–ma, 4aa–ma, and 5; single crystal data of 4ja, 4fb, and 4ma; UV–vis absorption spectra and optical properties of 4aa–ma. Acknowledgements The authors acknowledge Dr. Sudip Gorai, BARC, for his help in