Preparation of an advanced intermediate for the synthesis of leustroducsins and phoslactomycins by heterocycloaddition

• Anaïs Rousseau,
• Guillaume Vincent and
• Cyrille Kouklovsky

Beilstein J. Org. Chem. 2022, 18, 1385–1395, doi:10.3762/bjoc.18.143

• solvent using residual chloroform (7.26 ppm) as an internal reference. 13C NMR spectra were measured at 62.5, 75 or 90 MHz using residual chloroform (77.1 ppm) as an internal reference. High-resolution mass spectrometry (HRMS) analyses were conducted with electro spray ionization (ESI). 6

• , 1.5 Hz, 1H), 5.78 (dd, J = 10.2, 1.5 Hz, 1H), 3.68 (t, J = 6 Hz, 2H), 2.68 (t, J = 7.2 Hz, 2H), 1.86–1.77 (m, 2H), 1.00 (m, 21H) ppm; 13C NMR (75 MHz, CDCl3) δ 200.8, 136.7, 127.9, 62.4, 35.9, 27.2, 18.0, 12.0 ppm; HRMS (m/z): [M + Na]+ calcd 293.1907; found, 293.1898. (3Z)-3-Diethylphosphoryloxy-6

• = 17.3 Hz, 1H), 5.29 (dt, J = 7.2, 1.4 Hz, 1H), 5.08 (d, J = 10.8 Hz, 1H), 4.15–4.12 (m, 4H), 3.71 (t, J = 6.5 Hz, 2H), 2.48 (2dt, J = 7.2, 6.5 Hz, 2H), 1.31 (dt, J = 6.8, 1.1 Hz, 6H), 1.01 (m, 21H) ppm; 13C NMR (90 MHz, CDCl3) δ 146.2, 131.9, 118.0, 114.2, 64.4, 62.4, 30.0, 18.0, 16.2, 12.0 ppm; HRMS (m

Synthesis of C6-modified mannose 1-phosphates and evaluation of derived sugar nucleotides against GDP-mannose dehydrogenase

• Sanaz Ahmadipour,
• Alice J. C. Wahart,
• Jonathan P. Dolan,
• Laura Beswick,
• Chris S. Hawes,
• Robert A. Field and
• Gavin J. Miller

Beilstein J. Org. Chem. 2022, 18, 1379–1384, doi:10.3762/bjoc.18.142

• the intermediate C6–bromide to 11 was confirmed by 13C NMR, with C6 shifting downfield from δC 33.4 ppm to 51.6 ppm. Following this, dibenzyl phosphate was glycosylated with 11 using NIS/AgOTf activation of the thioglycoside, which proceeded in good yield (65%) to deliver 12. A final global

• n-BuLi at −78 °C. This afforded protected anomeric phosphate 16, confirmed by 1H and 13C NMR data (H1 δH 6.01 ppm, 3JH1–P = 6.7 Hz, 3JH1–H2 = 1.8 Hz; C1 δC 96.1 ppm, 2JC1–P = 5.9 Hz). Following an initial purification of 16 using silica gel flash chromatography, the material was crystallised using a

• : Detailed experimental protocols and characterisation data; spectral NMR data (1H, 13C and 31P NMR for compounds 10–17 and 19). Acknowledgements A clone encoding for GDP mannose-pyrophosphorylase from S. enterica was kindly donated by T. L. Lowary. Funding UK Research and Innovation (UKRI, Future Leaders

Cyclodextrin-based Schiff base pro-fragrances: Synthesis and release studies

• Attila Palágyi,
• Jindřich Jindřich,
• Juraj Dian and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2022, 18, 1346–1354, doi:10.3762/bjoc.18.140

• –97%). This method allows for easy recovery of the unreacted aldehyde as well as separation of the product (just by extraction by hexane and drying under reduced pressure) without its decomposition. The structure of the final imines was confirmed by 1H NMR, 13C NMR, ESI–MS, and the release of the VOCs

• the system. Sustained release of the aldehyde was demonstrated both in aqueous solutions and from a solid state upon humidity exposure. Experimental Instruments, general methods, and chemicals 1H NMR, 13C NMR, 2D NMR (H,H-COSY, HSQC, and HMBC) were measured on Bruker AVANCE III 600 MHz (600.17 MHz for

• 1H, 150.04 MHz for 13C) and Varian UNITYINOVA 400 (399,95 MHz for 1H and 100,58 MHz for 13C) spectrometers. For the kinetic studies, the 1H NMR spectra were acquired on a Varian VNMRS 300 spectrometer (300 MHz for 1H). DMSO-d6 and D2O were used as the solvents. The chemical shift values (δ) are given

Synthesis and electrochemical properties of 3,4,5-tris(chlorophenyl)-1,2-diphosphaferrocenes

• Almaz A. Zagidullin,
• Farida F. Akhmatkhanova,
• Mikhail N. Khrizanforov,
• Robert R. Fayzullin,
• Tatiana P. Gerasimova,
• Ilya A. Bezkishko and
• Vasili A. Miluykov

Beilstein J. Org. Chem. 2022, 18, 1338–1345, doi:10.3762/bjoc.18.139

• (chlorophenyl)ethynes 3b,c to form triarylcyclopropenylium salts 5b,c in 22 and 15% yield (Scheme 2). Unfortunately, it was not possible to synthesize tris(2-chlorophenyl)cyclopropenylium bromide 5a using this method. The structures of 3–5 were confirmed by 1H and 13C NMR as well as IR spectroscopic methods and

• , for 5c, single-crystal X-ray crystallography (Figure 1a). The 13C NMR signals of the cationic carbon atoms of the three-membered ring appeared at about 145 ppm. Besides, the 1H NMR spectra of 5 were unremarkable and consistent with the suggested formulas. As a next step, we synthesized a series of

• confirmed by 31P, 1H, and 13C NMR spectroscopy. The 31P{1H} NMR spectra of phosphonium bromides 6 showed a singlet at about 40 ppm, which is typical for phosphonium salts. The 13C{1H} NMR spectra consisted of a doublet at about 20 ppm, corresponding to the carbon atom C1, which is characteristic for the sp3

Ionic multiresonant thermally activated delayed fluorescence emitters for light emitting electrochemical cells

• Merve Karaman,
• Abhishek Kumar Gupta,
• Subeesh Madayanad Suresh,
• Tomas Matulaitis,
• Lorenzo Mardegan,
• Daniel Tordera,
• Henk J. Bolink,
• Sen Wu,
• Stuart Warriner,
• Ifor D. Samuel and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2022, 18, 1311–1321, doi:10.3762/bjoc.18.136

• synthetic strategy, which itself was synthesized from Br-DiKTa [28] following a Buchwald–Hartwig coupling. Details of the synthesis are found in Supporting Information File 1. The identity and purity of the molecules were verified using a combination of 1H and 13C NMR spectroscopy, high resolution mass

• File 250: 1H NMR and 13C NMR spectra, GC–MS, and HRMS; supplementary computational data and coordinates; additional photophysical. Acknowledgements We thank Dr. David Hall for providing help with the calculations and initial samples of some of the intermediates. Funding M. K. would like to thank 2214

Enantioselective total synthesis of putative dihydrorosefuran, a monoterpene with an unique 2,5-dihydrofuran structure

• Irene Torres-García,
• Josefa L. López-Martínez,
• Rocío López-Domene,
• Manuel Muñoz-Dorado,
• Ignacio Rodríguez-García and
• Miriam Álvarez-Corral

Beilstein J. Org. Chem. 2022, 18, 1264–1269, doi:10.3762/bjoc.18.132

• those published for the allegedly dihydrorosefuran isolated from Artemisia pallens nor with those reported for the compound from Tagetes mendocina (see Table 1 and Table 2). The 13C NMR data of compound 1 are quite similar to those of the natural product isolated from T. mendocina, except for the

• ), 1.70 (td, J = 0.5, 3.2 Hz, 3H), 1.25 (t, J = 7.1 Hz, 3H) ppm; 13C NMR (75 MHz, CDCl3, DEPT) δ 204.8 (C), 174.0 (C), 101.6 (C), 77.0 (CH2), 71.5 (CH), 60.5 (CH2), 30.4 (CH2), 30.0 (CH2), 14.5 (CH3), 14.2 (CH3) ppm; HRMS–ESI (Q-TOF, m/z): [M + H]+ calcd for C10H17O3, 185.1178; found, 185.1158. A lactone

• , 3H) ppm; 13C{1H} NMR (75 MHz, CDCl3, DEPT) δ 206.0 (C), 177.0 (C), 98.0 (C), 80.4 (CH), 77.5 (CH2), 28.5 (CH2), 26.1 (CH2), 15.0 (CH3) ppm; HRMS–ESI (Q-TOF, m/z): [M + H]+ calcd for C8H11O2,139.0759; found, 139.0782. Silver(I)-promoted cyclization of ethyl 4-hydroxy-5-methylhepta-5,6-dienoate (3) A

A one-pot electrochemical synthesis of 2-aminothiazoles from active methylene ketones and thioureas mediated by NH₄I

• Shang-Feng Yang,
• Pei Li,
• Zi-Lin Fang,
• Sen Liang,
• Hong-Yu Tian,
• Bao-Guo Sun,
• Kun Xu and
• Cheng-Chu Zeng

Beilstein J. Org. Chem. 2022, 18, 1249–1255, doi:10.3762/bjoc.18.130

• . Optimization of the reaction conditionsa. Supporting Information Supporting Information File 220: Experimental procedures, characterization data and copies of spectra of the all synthesized compounds (1H NMR, 13C NMR and HRMS). Funding This work was financially supported by the National Natural Science

From amines to (form)amides: a simple and successful mechanochemical approach

• Federico Casti,
• Rita Mocci and
• Andrea Porcheddu

Beilstein J. Org. Chem. 2022, 18, 1210–1216, doi:10.3762/bjoc.18.126

• assistance with the generation of the 1H, 13C NMR, and GC–MS spectroscopic data. Funding This research was funded by MIUR Italy, PRIN 2017 project (grant number: 2017B7MMJ5_001) “MultIFunctional poLymer cOmposites based on groWn matERials (MIFLOWER) and Fondazione di Sardegna (FdS, F72F20000230007).

Lewis acid-catalyzed Pudovik reaction–phospha-Brook rearrangement sequence to access phosphoric esters

• Jin Yang,
• Dang-Wei Qian and
• Shang-Dong Yang

Beilstein J. Org. Chem. 2022, 18, 1188–1194, doi:10.3762/bjoc.18.123

• . Proposed mechanism. Reaction optimization.a Supporting Information Supporting Information File 268: Experimental details and characterization data (1H, 13C, and 31P NMR as well as chromatograms) of products. Funding We are grateful to the NSFC (No. 22171119), Gansu Province Science and Technology Plan

Thermally activated delayed fluorescence (TADF) emitters: sensing and boosting spin-flipping by aggregation

• Ashish Kumar Mazumdar,
• Gyana Prakash Nanda,
• Nisha Yadav,
• Upasana Deori,
• Upasha Acharyya,
• Bahadur Sk and
• Pachaiyappan Rajamalli

Beilstein J. Org. Chem. 2022, 18, 1177–1187, doi:10.3762/bjoc.18.122

• Supporting Information File 1. Both compounds were further purified by temperature-gradient vacuum sublimation and characterized by 1H and 13C NMR spectroscopy (Figures S9–S12, Supporting Information File 1) as well as high-resolution mass spectrometry. Photophysical studies and DFT calculations The UV–vis

Experimental and theoretical studies on the synthesis of 1,4,5-trisubstituted pyrrolidine-2,3-diones

• Nguyen Tran Nguyen,
• Vo Viet Dai,
• Nguyen Ngoc Tri,
• Luc Van Meervelt,
• Nguyen Tien Trung and
• Wim Dehaen

Beilstein J. Org. Chem. 2022, 18, 1140–1153, doi:10.3762/bjoc.18.118

• signals of the aromatic carbons, the 13C NMR spectra of these compounds in DMSO-d6 also exhibited broad peaks at around 30 ppm and 191 ppm. The NMR spectra of the 2-pyrrolidinone derivative 4c were also recorded in CDCl3 and its 1H NMR spectrum is similar to the one observed in DMSO-d6. However, the 13C

• NMR spectrum of 4c in CDCl3 showed sharp peaks at 29.21 ppm and 194.61 ppm representing the two carbon atoms of the acetyl group attached to the 4-postion of the heterocyclic five-membered ring. Therefore, the broadening of peaks observed in the 13C NMR spectra is due to the tautomerism of compounds

• shown in solvent models used in this work. Conclusion 4-Acetyl-3-hydroxy-3-pyrrolin-2-ones were synthesized successfully via the three-component reaction of an aromatic aldehyde, aniline, and ethyl 2,4-dioxovalerate with acceptable yields. The broadening of peaks in the 13C NMR spectra for the two

Electrogenerated base-promoted cyclopropanation using alkyl 2-chloroacetates

• Kouichi Matsumoto,
• Yuta Hayashi,
• Kengo Hamasaki,
• Mizuki Matsuse,
• Hiyono Suzuki,
• Keiji Nishiwaki and
• Norihito Kawashita

Beilstein J. Org. Chem. 2022, 18, 1116–1122, doi:10.3762/bjoc.18.114

• Information File 100: Experimental details, characterization data of new compounds and copies of 1H NMR and 13C NMR spectra. Acknowledgements We are grateful to the Kindai University Joint Research Center for the use of facilities. We also appreciate the reviewers for fruitful suggestion. Funding This work

Radical cation Diels–Alder reactions of arylidene cycloalkanes

• Kaii Nakayama,
• Hidehiro Kamiya and
• Yohei Okada

Beilstein J. Org. Chem. 2022, 18, 1100–1106, doi:10.3762/bjoc.18.112

• Information File 96: General remarks, photocatalyst analyzation data, synthesis procedure, additional control studies, electrochemical measurements, and characterization data, including copies of 1H and 13C NMR spectra. Funding This work was supported in part by JSPS KAKENHI grant Nos. 16H06193, 17K19221

Synthesis of N-phenyl- and N-thiazolyl-1H-indazoles by copper-catalyzed intramolecular N-arylation of ortho-chlorinated arylhydrazones

• Yara Cristina Marchioro Barbosa,
• Guilherme Caneppele Paveglio,
• Claudio Martin Pereira de Pereira,
• Sidnei Moura,
• Cristiane Storck Schwalm,
• Gleison Antonio Casagrande and
• Lucas Pizzuti

Beilstein J. Org. Chem. 2022, 18, 1079–1087, doi:10.3762/bjoc.18.110

• . All products were fully characterized by HRMS as well as 1H and 13C NMR spectroscopy. Thus, this approach is valuable for promoting the synthesis of N-phenyl-1H-indazoles in a higher yield than that reported in the literature using copper catalysis and the same substrates. This study also prompted the

• conditions and yields. When arylhydrazone 1i or 3i, respectively, was the starting material, competition between attack of the nitrogen atom on position 2 (C−Cl) and 6 (C−F) was observed (Scheme 2). The analysis of the 1H NMR (Figure S31, Supporting Information File 1), 13C NMR (Figure S32, Supporting

• mixture of 4i and 4i’, as concluded from the analysis of the 1H NMR (Figure S45, Supporting Information File 1), 13C NMR (Figure S46, Supporting Information File 1), and HRMS spectra (Figures S79 and S80, Supporting Information File 1). However, 4i was detected as the major product in the ratio 10:6, as

Facile and diastereoselective arylation of the privileged 1,4-dihydroisoquinolin-3(2H)-one scaffold

• Dmitry Dar’in,
• Grigory Kantin,
• Alexander Bunev and
• Mikhail Krasavin

Beilstein J. Org. Chem. 2022, 18, 1070–1078, doi:10.3762/bjoc.18.109

• substituent and an N-alkyl group (considering that N-aryl nitrophenyl-substituted compound 10o was obtained in a respectable 91% yield). The structures of compounds 10a–s were unequivocally confirmed by 1H and 13C NMR spectroscopy (paying a particular attention to the appearance of the C=N2 signal in the

• ). Using more reactive (electron-rich) arenes results in lower diastereoselectivity and regiospecificity of the reaction (cf. 9q, 9v, and 9w). The structure and the initially anticipated trans-configuration of the products 9 was unequivocally confirmed by 1H and 13C NMR spectroscopy as well as, in the case

Synthesis, optical and electrochemical properties of (D–π)₂-type and (D–π)₂Ph-type fluorescent dyes

• Kosuke Takemura,
• Kazuki Ohira,
• Taiki Higashino,
• Keiichi Imato and
• Yousuke Ooyama

Beilstein J. Org. Chem. 2022, 18, 1047–1054, doi:10.3762/bjoc.18.106

• OTT-2 to OTK-2. Experimental General methods Melting points were measured with an AS ONE ATM-02 apparatus. IR spectra were recorded on a SHIMADZU IRTracer-100 spectrometer by ATR method. 1H NMR and 13C NMR spectra were recorded on a Varian-500 FT NMR spectrometer. High-resolution mass spectral data by

• (dd, J = 1.8 and 8.4 Hz, 2H), 7.01–7.05 (m, 4H), 7.10–7.16 (m, 10H), 7.24–7.31 (m, 10H), 7.39 (d, J = 3.8 Hz, 2H), 7.50 (dd, J = 1.4 and 8.0 Hz, 2H), 7.59 (d, J = 1.2 Hz, 2H), 7.93 (d, J = 8.3 Hz, 2H), 7.99 (d, J = 8.0 Hz, 2H) ppm; 13C NMR (125 MHz, CD2Cl2) δ 14.04, 20.85, 31.44, 43.04, 105.37, 105.84

• of OTK-2 and OTT-2. Optical data of OTK-2 [33] and OTT-2 in toluene. Optical data of OTK-2 [33] and OTT-2 in the solid-state. Electrochemical data, and HOMO and LUMO energy levels of OTK-2 and OTT-2. Supporting Information Supporting Information File 182: 1H and 13C NMR spectra of OTT-2. Funding

Electrochemical Friedel–Crafts-type amidomethylation of arenes by a novel electrochemical oxidation system using a quasi-divided cell and trialkylammonium tetrafluoroborate

• Hisanori Senboku,
• Mizuki Hayama and
• Hidetoshi Matsuno

Beilstein J. Org. Chem. 2022, 18, 1040–1046, doi:10.3762/bjoc.18.105

• trialkylammonium salts, general procedure for electrolysis, spectral data information including 1H and 13C NMR spectra of new compounds. Acknowledgements We would like to thank Professor Tomoki Yoneda, Hokkaido University, for his helpful discussion and support for NMR measurement at 150 °C. 1H and 13C NMR

A versatile way for the synthesis of monomethylamines by reduction of N-substituted carbonylimidazoles with the NaBH₄/I₂ system

• Lin Chen,
• Xuan Zhou,
• Zhiyong Chen,
• Changxu Wang,
• Shunjie Wang and
• Hanbing Teng

Beilstein J. Org. Chem. 2022, 18, 1032–1039, doi:10.3762/bjoc.18.104

• were all transformed, affording the expected products in 70–85% yields. N-Aryl carbonylimidazoles with two substituents, such as 12b (R1 = methyl, R2 = phenyl) and 13b (R1 = phenyl, R2 = phenyl), were also amenable to this protocol, giving the corresponding products 12c and 13c in 71% and 67% yield

Electrochemical vicinal oxyazidation of α-arylvinyl acetates

• Yi-Lun Li,
• Zhaojiang Shi,
• Tao Shen and
• Ke-Yin Ye

Beilstein J. Org. Chem. 2022, 18, 1026–1031, doi:10.3762/bjoc.18.103

• . Derivatization of α-azidoketone 2. Proposed mechanism. Optimization of reaction conditions.a Supporting Information Supporting Information File 186: Experimental procedures, characterization data, copies of 1H and 13C NMR spectra. Funding Financial support from the National Natural Science Foundation of China

New azodyrecins identified by a genome mining-directed reactivity-based screening

• Atina Rizkiya Choirunnisa,
• Kuga Arima,
• Yo Abe,
• Noritaka Kagaya,
• Kei Kudo,
• Hikaru Suenaga,
• Junko Hashimoto,
• Manabu Fujie,
• Noriyuki Satoh,
• Kazuo Shin-ya,
• Kenichi Matsuda and
• Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2022, 18, 1017–1025, doi:10.3762/bjoc.18.102

• Streptomyces sp. RM72 were first partitioned by water and ethyl acetate, and then the organic layer was further fractionated by silica gel column chromatography. Fractionation by reversed-phase HPLC yielded ten compounds (1–10) that generate N2H4 upon acid hydrolysis. The combination of 1H and 13C NMR with a

• in the Refseq database. Nodes are colored according to the host organism’s order. Enzymes with known biosynthetic products are colored red. N2H4-detecting colorimetric assay. Proposed biosynthetic pathway of azodyrecin. 1H (500 MHz) and 13C (125 MHz) NMR data for azodyrecin D (7), azodyrecin E (8

• ), azodyrecin F (9), and azodyrecin G (10).a Cytotoxicities of compound 2, 5, 7, and 8. Supporting Information Supporting Information File 122: Experimental procedures, characterization data (1H, 13C NMR, and HRMS) and biochemical characterization of recombinant Ady1. Acknowledgements We thank to Dr. Eri

Isolation and biosynthesis of daturamycins from Streptomyces sp. KIB-H1544

• Yin Chen,
• Jinqiu Ren,
• Ruimin Yang,
• Jie Li,
• Sheng-Xiong Huang and
• Yijun Yan

Beilstein J. Org. Chem. 2022, 18, 1009–1016, doi:10.3762/bjoc.18.101

• 12 degrees of unsaturation based on the HRMS–ESI data (m/z 347.0893 [M + Na]+, calcd for C19H16O5Na+, 347.0890) (Figure S1, Supporting Information File 1). Comprehensive analysis of the 1H and 13C NMR data (Table 1, Figures S3 and S4, Supporting Information File 1) and HSQC data (Figure S5

• suggested that the relative configurations of C-4 and C-5 were trans. Therefore, the structure of compound 2 has been determined, as shown in Figure 1. However, the absolute configuration of compound 2 remained unsolved. Daturamycin C (3) was obtained as a brown powder, and the 1H and 13C NMR spectra

• crystallography (Figure 2). The known congeners were determined as terferol (4) [20], BTH-II0204-207: D (5) [21], and betulinan A (6) [22] (Figure 1) by comparing their 1H and 13C NMR spectroscopic data (Figures S16–S21, Supporting Information File 1) and specific rotation values with those in the literatures

Automated grindstone chemistry: a simple and facile way for PEG-assisted stoichiometry-controlled halogenation of phenols and anilines using N-halosuccinimides

• Dharmendra Das,
• Akhil A. Bhosle,
• Amrita Chatterjee and
• Mainak Banerjee

Beilstein J. Org. Chem. 2022, 18, 999–1008, doi:10.3762/bjoc.18.100

• . Moreover, up to 95% of the side product succinimide was also isolated, and considering its possible conversion to NBS [44] it is an attribute to this green protocol by lowering the E-factor. The products were well-characterized by 1H NMR, 13C NMR, IR, and CHN analysis. The NMR spectra of the synthesized

Molecular diversity of the base-promoted reaction of phenacylmalononitriles with dialkyl but-2-ynedioates

• Hui Zheng,
• Ying Han,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2022, 18, 991–998, doi:10.3762/bjoc.18.99

• in the reaction. Because there is only one chiral carbon atom in the molecule, there are no diastereoisomers in the obtained products 3a–l. The chemical structures of compounds 3a–l were fully characterized by IR, HRMS, 1H and 13C NMR spectra. As for an example, the 1H NMR spectrum of compound 3i

• dialkyl but-2-ynedioate. Thus, a quasi-four-component reaction led to the final product. There are two chiral carbon atoms in the molecules, thus two diastereoisomers would be formed in the reaction. However, the 1H and 13C NMR spectra gave only one set of resonances for the characteristic groups, which

• , 1H, CH2), 2.36 (s, 3H, CH3), 1.41 (t, J = 6.8 Hz, 3H, CH3), 1.14 (t, J = 6.8 Hz, 3H, CH3); 13C NMR (100 MHz, CDCl3) δ 163.2, 159.2, 152.7, 139.0, 136.8, 129.6, 129.5, 124.7, 113.7, 113.5, 86.9, 63.2, 62.7, 52.3, 38.1, 21.1, 13.9, 13.7; HRMS–ESI (m/z): [M + Na]+ calcd for C20H20NaN2O5, 391.1270; found

First example of organocatalysis by cathodic N-heterocyclic carbene generation and accumulation using a divided electrochemical flow cell

• Daniele Rocco,
• Ana A. Folgueiras-Amador,
• Richard C. D. Brown and
• Marta Feroci

Beilstein J. Org. Chem. 2022, 18, 979–990, doi:10.3762/bjoc.18.98

• by staining with potassium permanganate. Flash column chromatography was performed using high purity silica gel, pore size 60 Å, 230–400 mesh particle size, purchased from Merck. 1H NMR and 13C NMR spectra were recorded in CDCl3 (purchased from Cambridge Isotope Laboratories) at 298 K using a Bruker

• DPX400 (400 and 101 MHz, respectively) spectrometer. Chemical shifts are reported on the δ scale in ppm and were referenced to residual solvent (CDCl3: 7.27 ppm for 1H NMR spectra and 77.0 ppm for 13C NMR spectra). Coupling constants (J) were given in Hz and matched where possible. The following

• -Butyl-3-methyl-1H-imidazole-2(3H)-thione (1a): Spectral data are consistent with those reported in the literature [38]. 1H NMR (CDCl3) δ 6.64 (s, 2H), 3.99 (t, J = 7.4 Hz, 2H), 3.57 (s, 3H), 1.79–1.64 (m, 2H), 1.39–1.28 (m, 2H), 0.92 (t, J = 7.3 Hz, 3H) ppm; 13C NMR (CDCl3) δ 162.3, 117.5, 116.4, 47.8

Electroreductive coupling of 2-acylbenzoates with α,β-unsaturated carbonyl compounds: density functional theory study on product selectivity

• Naoki Kise and
• Toshihiko Sakurai

Beilstein J. Org. Chem. 2022, 18, 956–962, doi:10.3762/bjoc.18.95

• cyclization step. Experimental General information. The 1H NMR (500 MHz) and 13C NMR (125 MHz) spectra were measured on a JEOL GMX-500 spectrometer with tetramethylsilane (TMS) or the residual signals of protonated solvents as an internal standard: CDCl3 (δ = 77.0 in 13C NMR). IR spectra were recorded on a

• Information Supporting Information File 215: Characterization data for compounds, copies of 1H and 13C NMR spectra, X-ray crystallographic data (ORTEP) of 3b, CV data of compounds 1a–h, and DFT calculation data for cyclization of enolate anions. Supporting Information File 216: Cif for 3b. Acknowledgements