Controlling the reactivity of La@C₈₂ by reduction: reaction of the La@C₈₂ anion with alkyl halide with high regioselectivity

• Yutaka Maeda,
• Saeka Akita,
• Mitsuaki Suzuki,
• Michio Yamada,
• Takeshi Akasaka,
• Kaoru Kobayashi and
• Shigeru Nagase

Beilstein J. Org. Chem. 2023, 19, 1858–1866, doi:10.3762/bjoc.19.138

Enabling artificial photosynthesis systems with molecular recycling: A review of photo- and electrochemical methods for regenerating organic sacrificial electron donors

• Grace A. Lowe

Beilstein J. Org. Chem. 2023, 19, 1198–1215, doi:10.3762/bjoc.19.88

• organic donors. The authors designed and synthesized a tertiary amine that could be oxidized and rehydrogenated. They used their amine to successfully replace triethylamine in a photocatalytic carbon dioxide reduction reaction from the literature and proved that the recyclable byproduct was formed. In

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

• the next step without further purification. DMSO (0.16 mL, 2.241 mmol, 3 equiv) was added dropwide to a cooled (−78 °C) solution of oxalyl chloride (0.1 mL, 1.121 mmol, 1.5 equiv) in dichloromethane (3.4 mL). After stirring 15 min at −78 °C, a solution of the crude product from reduction reaction (300

Cathodic generation of reactive (phenylthio)difluoromethyl species and its reactions: mechanistic aspects and synthetic applications

• Sadanobu Iwase,
• Shinsuke Inagi and
• Toshio Fuchigami

Beilstein J. Org. Chem. 2022, 18, 872–880, doi:10.3762/bjoc.18.88

• peak current disappeared completely as shown in Figure 1c. The reduction peak potential of 1 is −2.4 V vs. SSCE, which excludes the reduction of 1 at this potential. Therefore, the enhanced cathodic current of o-phthalonitrile clearly suggests that a typical electrocatalytic reduction reaction takes

Tri(n-butyl)phosphine-promoted domino reaction for the efficient construction of spiro[cyclohexane-1,3'-indolines] and spiro[indoline-3,2'-furan-3',3''-indolines]

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

Beilstein J. Org. Chem. 2022, 18, 669–679, doi:10.3762/bjoc.18.68

• of readily available 1,3-dipolarophile, 3-phenacylidenoxindole, was also tested in the reaction. However, it was found that the C=C bond in 3-phenacylidenoxindole was directly reduced to give the corresponding saturated 3-(2-oxo-2-phenylethyl)indolin-2-one. A similar reduction reaction of 3

Menadione: a platform and a target to valuable compounds synthesis

• Acácio S. de Souza,
• Ruan Carlos B. Ribeiro,
• Dora C. S. Costa,
• Fernanda P. Pauli,
• David R. Pinho,
• Matheus G. de Moraes,
• Fernando de C. da Silva,
• Luana da S. M. Forezi and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

• photoreactor. It was observed that the presence of free hydroxy groups in 70 was essential for the quinone reduction reaction to occur, when compared to the 2,3-di-O-methylated derivative (70, R = Me). Under the reported conditions, the reduction of menadione (10) gave compound 14 in 42% yield after 80 hours

Site-selective reactions mediated by molecular containers

• Rui Wang and
• Yang Yu

Beilstein J. Org. Chem. 2022, 18, 309–324, doi:10.3762/bjoc.18.35

• mode, the molecular container selectively binds with and shields a certain part of the guest molecule and leaves the remaining part exposed to the reaction medium. This methodology was firstly applied to the site-selective reduction reaction mediated by a cyclodextrin host. In 1991, the Takahashi group

Design, synthesis and photophysical properties of novel star-shaped truxene-based heterocycles utilizing ring-closing metathesis, Clauson–Kaas, Van Leusen and Ullmann-type reactions as key tools

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2021, 17, 1374–1384, doi:10.3762/bjoc.17.96

• from the same starting material 1 by employing the acid-catalyzed cyclotrimerization, alkylation and subsequent reduction reaction sequences (path B, Scheme 1). In sharp contrast, as can be inspected from path C (Scheme 1) title compound 6 was also synthesized from the tribromotruxene derivative 5 by

Syntheses and chemical properties of β-nicotinamide riboside and its analogues and derivatives

• Mikhail V. Makarov and
• Marie E. Migaud

Beilstein J. Org. Chem. 2019, 15, 401–430, doi:10.3762/bjoc.15.36

• dihydropyridines has been well studied and extensively reviewed [61][62][63][64]. It was demonstrated that the outcome of the reduction reaction is dependent on many factors, such as the electron withdrawing/releasing properties and locations of the substituents on the pyridinium core. They also depend on the

Synthesis, biophysical properties, and RNase H activity of 6’-difluoro[4.3.0]bicyclo-DNA

• Sibylle Frei,
• Adam K. Katolik and
• Christian J. Leumann

Beilstein J. Org. Chem. 2019, 15, 79–88, doi:10.3762/bjoc.15.9

• formation of the nucleoside 6 took place, they had to be analyzed separately. Therefore, a sample of the iodinated nucleosides 2α/β was purified and subjected to the reduction reaction, where nucleosides 5α/β were formed as single products (Table 1, entry 2). Also, the conversion of the nucleosides 5α/β

Bioinspired cobalt cubanes with tunable redox potentials for photocatalytic water oxidation and CO₂ reduction

• Zhishan Luo,
• Yidong Hou,
• Jinshui Zhang,
• Sibo Wang and
• Xinchen Wang

Beilstein J. Org. Chem. 2018, 14, 2331–2339, doi:10.3762/bjoc.14.208

• μmol·h−1). It is found that the introduction of a simple substituent greatly influenced the activity of CO2 reduction, that is, the ligand substitution with an electron-donating property is more beneficial for the CO2 reduction reaction. The above results demonstrate that the 1-R molecular complexes are

• test for CO2 reduction system [70]: The photocatalytic test was performed in a Schlenk flask (80 mL) under an atmospheric pressure of CO2. In the Schlenk flask, the photocatalytic CO2 reduction reaction was carried out by dispersing Ru(bpy)32+ (7.8 mg) in MeCN (4 mL) containing triethanolamine (TEOA, 1

Spectroelectrochemical studies on the effect of cations in the alkaline glycerol oxidation reaction over carbon nanotube-supported Pd nanoparticles

• Dennis Hiltrop,
• Steffen Cychy,
• Karina Elumeeva,
• Wolfgang Schuhmann and
• Martin Muhler

Beilstein J. Org. Chem. 2018, 14, 1428–1435, doi:10.3762/bjoc.14.120

• AFCs have several advantages over PEMFCs such as faster kinetics of the oxygen reduction reaction at the cathode, greater longevity and the possible adaption of less precious metals due to the alkaline electrolyte [6][7]. In direct alkaline alcohol FCs (DAAFCs) electricity is generated by oxidizing

Recent applications of chiral calixarenes in asymmetric catalysis

• Mustafa Durmaz,
• Erkan Halay and
• Selahattin Bozkurt

Beilstein J. Org. Chem. 2018, 14, 1389–1412, doi:10.3762/bjoc.14.117

• have been prepared from enantiopure chiral hemispherical calix[4]arene ligands 115a–c in which the asymmetric carbon is directly attached to the calixarene lower rim as shown by Katz et al. (Scheme 35) for the asymmetric Meerwein−Ponndorf−Verley (MPV) reduction reaction [72]. Chiral sec-butylalcohol

Nanoreactors for green catalysis

• M. Teresa De Martino,
• Loai K. E. A. Abdelmohsen,
• Floris P. J. T. Rutjes and
• Jan C. M. van Hest

Beilstein J. Org. Chem. 2018, 14, 716–733, doi:10.3762/bjoc.14.61

• ]. Thiol functionalized PEG blocks were immobilized on Au NPs. PS segments improved the stability of the system and provided the necessary hydrophobic environment that is required to undertake the reduction reaction in water. The outcome of using Au@PEG-PS as nanoreactors was compared to those resulting

• , highlighting the significance of the nanoreactor design (Figure 8). Superior catalytic activity of Au@PEG-b-PS was observed in the reduction reaction of 4-nitrophenol to 4-aminophenol. The catalytic activity increased with the decrease in the chain length of the PS block. In addition, the high stability

Sugar-based micro/mesoporous hypercross-linked polymers with in situ embedded silver nanoparticles for catalytic reduction

• Qing Yin,
• Qi Chen,
• Li-Can Lu and
• Bao-Hang Han

Beilstein J. Org. Chem. 2017, 13, 1212–1221, doi:10.3762/bjoc.13.120

• , the related catalytic activity of the composite tends to decrease with the increase in the size of the AgNPs. Therefore, the reaction time should not be too long. We found that the optimized loading reaction time was about 24 h. In the presence of excess BH4−, the catalytic reduction reaction mediated

• room temperature by recording absorbance from 244–600 nm within defined time intervals. The reduction reaction was conducted within minutes after the solution was prepared to minimize decomposition of NaBH4. 13C CP/MAS NMR spectrum of SugPOP-3. (a) Nitrogen adsorption–desorption isotherms of SugPOP-1–3

A versatile route to polythiophenes with functional pendant groups using alkyne chemistry

• Xiao Huang,
• Li Yang,
• Rikard Emanuelsson,
• Jonas Bergquist,
• Maria Strømme,
• Martin Sjödin and
• Adolf Gogoll

Beilstein J. Org. Chem. 2016, 12, 2682–2688, doi:10.3762/bjoc.12.265

• from −1.2 to 0.6 V vs ferrocene/ferrocenium (Fc+/Fc0) during polymerization cycling. Apparently, the presence of an ethynyl group on pyEDOT did not disturb the polymerization of the EDOT backbone. The CVs of pyEDOT indicated an irreversible reduction reaction at a potential lower than −2.4 V vs Fc+/Fc0

Robust C–C bonded porous networks with chemically designed functionalities for improved CO₂ capture from flue gas

• Damien Thirion,
• Joo S. Lee,
• Ercan Özdemir and
• Cafer T. Yavuz

Beilstein J. Org. Chem. 2016, 12, 2274–2279, doi:10.3762/bjoc.12.220

• linker used for COP-157 is linear [22][23]. After post-modification, the surface area diminishes, which is a common observation [13][24]. Yet, the pore volume of COP-156-amine increases to 0.99 cm3/g at P/P0 = 0.99, due to newly created pores from the reduction reaction (Figure 2). COP-156-amidoxime has

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

• David R. Chisholm,
• Garr-Layy Zhou,
• Ehmke Pohl,
• Roy Valentine and
• Andrew Whiting

Beilstein J. Org. Chem. 2016, 12, 1851–1862, doi:10.3762/bjoc.12.174

• effects in terms of the chromophoric properties of the resulting systems and an improved synthesis of 22 was therefore pursued. In light of its formation by LiAlH4, we anticipated that production of 22 would be favoured if the intermediate tetrahedral complex in the reduction reaction was more stable. An

Photovoltaic-driven organic electrosynthesis and efforts toward more sustainable oxidation reactions

• Bichlien H. Nguyen,
• Robert J. Perkins,
• Jake A. Smith and
• Kevin D. Moeller

Beilstein J. Org. Chem. 2015, 11, 280–287, doi:10.3762/bjoc.11.32

• conducting a wide variety of sustainable oxidation reactions. The approach presented in this article is compatible with both direct and indirect oxidation reactions, avoids the need for a stoichiometric oxidant, and leads to hydrogen gas as the only byproduct from the corresponding reduction reaction

• material to keep current densities low. All of the RVC electrodes used were of 100 pores per inch and approximately 1 × 1 cm in size, and thus the differences in current are directly proportional to the current density from experiment to experiment. An equal but opposite reduction reaction happens at the

• cathode. For all of the oxidation reactions highlighted in this work, this reduction reaction leads to the formation of hydrogen gas. In addition to the direct oxidation of a substrate described in the preceding paragraph, indirect electrochemical methods also offer a powerful means of recycling chemical

Synthesis of chiral N-phosphinyl α-imino esters and their application in asymmetric synthesis of α-amino esters by reduction

• Yiwen Xiong,
• Haibo Mei,
• Lingmin Wu,
• Jianlin Han,
• Yi Pan and
• Guigen Li

Beilstein J. Org. Chem. 2014, 10, 653–659, doi:10.3762/bjoc.10.57

• -substituent led to lower yield due to steric effects (Table 2, entry 7). Besides, the reaction with ethyl ester also worked well and resulted in a slightly lower yield (Table 2, entry 11). Optimization of the asymmetric reduction reaction conditions Then, the obtained chiral N-phosphinyl α-imino esters were

• temperature influenced the reaction obviously, and raising the temperature to −40 °C reduces the yield to 89% and the diastereoselectivity to 87:13 (Table 3, entry 14). Scope of the asymmetric reduction reaction After getting the optimized reduction conditions, several chiral N-phosphinyl α-imino esters

Substrate dependent reaction channels of the Wolff–Kishner reduction reaction: A theoretical study

• Shinichi Yamabe,
• Guixiang Zeng,
• Wei Guan and
• Shigeyoshi Sakaki

Beilstein J. Org. Chem. 2014, 10, 259–270, doi:10.3762/bjoc.10.21

• product. For both ketone substrates, the diimines undergoing E2 reactions were found to be key intermediates. Keywords: acetone; acetophenone; DFT calculations; diimine intermediate; reduction reaction; transition states; Wolff–Kishner; Introduction The Wolff–Kishner (W-K) reduction is an organic

• reduction reaction. The employed model is shown in Scheme 4a and is composed of acetone, hydrazine and (H2O)8. From (x) (trans-diimine and (H2O)9, there are two routes to the (xii) (product). One is (x) → (xi) → (xii) in this Figure. The other one is shown in Figure S1 (Supporting Information File 1

• ). Distances are in Å. Energy changes of the neutral W-K reaction of acetone. Geometric changes are shown in Figure 1 and Figure S1 (Supporting Information File 1). Geometric changes of the base-promoted Wolff–Kishner reduction reaction. The model employed is shown in Scheme 4b and is composed of acetone

Copper(II)-salt-promoted oxidative ring-opening reactions of bicyclic cyclopropanol derivatives via radical pathways

• Eietsu Hasegawa,
• Minami Tateyama,
• Ryosuke Nagumo,
• Eiji Tayama and
• Hajime Iwamoto

Beilstein J. Org. Chem. 2013, 9, 1397–1406, doi:10.3762/bjoc.9.156

• hexenyl radical cyclization reactions [21], (Figure 1) [22][23][24][25][26][27][28][29][30]. For example, PET reactions of probe I with amines were observed to produce a spirocyclic ketone product while its reduction reaction induced by samarium diiodide (SmI2) gives rise to a cyclopropanol (left in

Continuous preparation of carbon-nanotube-supported platinum catalysts in a flow reactor directly heated by electric current

• Alicja Schlange,
• Antonio Rodolfo dos Santos,
• Ulrich Kunz and
• Thomas Turek

Beilstein J. Org. Chem. 2011, 7, 1412–1420, doi:10.3762/bjoc.7.165

• results. Most of the work is concerned with the precipitation of hydroxides, oxides or other hardly soluble metal compounds [12]. Platinum nanoparticles supported on conductive carbon materials such as carbon black or carbon nanotubes (CNTs) are commonly used as oxygen reduction reaction (ORR) catalysts

Miniemulsion polymerization as a versatile tool for the synthesis of functionalized polymers

• Daniel Crespy and
• Katharina Landfester

Beilstein J. Org. Chem. 2010, 6, 1132–1148, doi:10.3762/bjoc.6.130

• droplets followed by polymerization of the dispersed phase [22]. The reduction reaction was performed at high temperature and miniemulsions were kept stable. This novel system opens up the area of high temperature reactions in miniemulsion. Acrylic acid was also copolymerized with trivinylacrylic acid in

Prediction of reduction potentials from calculated electron affinities for metal-salen compounds

• Sarah B. Bateni,
• Kellie R. England,
• Anthony T. Galatti,
• Handeep Kaur,
• Victor A. Mendiola,
• Alexander R. Mitchell,
• Michael H. Vu,
• Benjamin F. Gherman and
• James A. Miranda

Beilstein J. Org. Chem. 2009, 5, No. 82, doi:10.3762/bjoc.5.82

• then the opposite of the enthalpy change for the 1-electron reduction reaction (Equation 2). The choice of density functional to employ here was made from among the pure density functionals BLYP [14][15], OLYP [15][16], and HCTH [17] and the hybrid density functionals B3LYP [14][15][18], O3LYP [15][16