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Search for "electrosynthesis" in Full Text gives 40 result(s) in Beilstein Journal of Organic Chemistry.
A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis
Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214
- , 52074, Aachen, Germany 10.3762/bjoc.20.214 Abstract With the resurgence of electrosynthesis in organic chemistry, there is a significant increase in the number of routes available for late-stage functionalization (LSF) of drugs. Electrosynthetic methods, which obviate the need for hazardous chemical
- reactors for industrial applications. The potential for upscaling and applicability towards LSF makes electrosynthesis particularly appealing for the fine-chemical and pharmaceutical industry. As the electrode potential can be fine-tuned over a continuous scale, higher functional group compatibility can be
- achieved compared to many classical methods. In light of the general trend towards more chemoselective protocols with broader functional group compatibility, there has been a growing interest in exploring the potential of electrosynthesis for the late-stage functionalization of complex scaffolds
Electrochemical allylations in a deep eutectic solvent
Beilstein J. Org. Chem. 2024, 20, 2217–2224, doi:10.3762/bjoc.20.189
- Sophia Taylor Scott T. Handy Department of Chemistry, Middle Tennessee State University, Murfreesboro, TN, USA 10.3762/bjoc.20.189 Abstract Electrosynthesis is a technique that is attracting increased attention and has many appealing features, particularly its potential greenness. At the same
- time, electrosynthesis requires a solvent and a supporting electrolyte in order for current to pass through the reaction. These are effectively consumable reagents unless a convenient means of recycling can be developed. As part of our interest in unusual solvents and electrochemistry, we explored the
- used, offering an interesting new option for electrochemical allylations. Keywords: allylation; electrosynthesis; eutectic solvent; recycling; tin; Introduction The last several years have witnessed a tremendous resurgence of interest in electrochemistry in the area of organic synthesis [1]. While
Harnessing the versatility of hydrazones through electrosynthetic oxidative transformations
Beilstein J. Org. Chem. 2024, 20, 1988–2004, doi:10.3762/bjoc.20.175
- access to diazo compounds as either synthetic intermediates or products. A special attention is paid to the reaction mechanism with the aim to encourage further development in this field. Keywords: C–H functionalization; diazo compound; electrosynthesis; hydrazone; nitrogen-containing heterocycle
- hydrazones is of significant importance and can contribute to the formation of novel organic compounds. Electrosynthesis enables the generation of either radical, radical ionic or ionic species [29] under mild and environmentally friendly reaction conditions [30][31]. The direct use of electrical current to
- atom abstraction by iodide radical and deprotonation. Inspired by these works, Li and Gu et al. proposed the electrosynthesis of 1,3,5-trisubstituted 1,2,4-triazoles from preformed aldehyde-derived N-arylhydrazones 60, aldehydes 61 and ammonium acetate. Herein, the authors suggested the electromediated
Novel oxidative routes to N-arylpyridoindazolium salts
Beilstein J. Org. Chem. 2024, 20, 1906–1913, doi:10.3762/bjoc.20.166
- amine oxidation is increased. Electrochemical synthesis of pyridoindazolium salts The results of the voltammetry testing allowed to assume that pyridoindazolium salts can also be obtained using an anodic synthesis. Electric current as a reagent is inherently safe and easily scalable; electrosynthesis is
Synthesis of polycyclic aromatic quinones by continuous flow electrochemical oxidation: anodic methoxylation of polycyclic aromatic phenols (PAPs)
Beilstein J. Org. Chem. 2024, 20, 1746–1757, doi:10.3762/bjoc.20.153
- alternative to classical synthesis [25][26][27][28]. Electrochemical oxidation reactions are further used to emulate enzymatic oxidations of drugs and explore potential metabolites [29][30][31]. Electrochemical flow systems provide fast electrosynthesis with low cell resistance, large electrode area, and good
Additive-controlled chemoselective inter-/intramolecular hydroamination via electrochemical PCET process
Beilstein J. Org. Chem. 2024, 20, 264–271, doi:10.3762/bjoc.20.27
- 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as an additive. These results provide fundamental insights for the design of PCET-based redox reaction systems under electrochemical conditions. Keywords: amidyl radical; cyclic voltammetry; electrosynthesis; hydroamination; proton coupled electron transfer
A new oxidatively stable ligand for the chiral functionalization of amino acids in Ni(II)–Schiff base complexes
Beilstein J. Org. Chem. 2023, 19, 566–574, doi:10.3762/bjoc.19.41
- including the thiolation discussed above). Insertion of the t-Bu group also makes the (GlyNi)L7 complex more soluble in diethyl ether as compared to the parent (GlyNi)L1 complex (21.3 mg/1 mL vs <1 mg/1 mL in Et2O; see Figure 3). This is beneficial for electrosynthesis, simplifying the separation of the
Molecular and macromolecular electrochemistry: synthesis, mechanism, and redox properties
Beilstein J. Org. Chem. 2022, 18, 1505–1506, doi:10.3762/bjoc.18.158
- /bjoc.18.158 Keywords: electron transfer; electrosynthesis; organic electrochemistry; redox-active materials; Electrochemistry is now a powerful tool in organic chemistry not only for analyzing the electron transfer behavior of organic molecules and macromolecules, but also for driving organic
- reactions to produce value-added products. Electrochemical synthesis (or simply electrosynthesis) is increasingly recognized for the high academic and industrial importance, in line with the concept of green chemistry proposed in 1998 and the Sustainable Development Goals (SDGs) adopted by the United
- Nations in 2015. This is evidenced by the recent publication of special issues on organic electrosynthesis in various academic journals [1][2][3][4][5]. In addition to the conventional two- or three-electrode batch-type electrolytic cells, recent developments include microflow electrolytic reactors
Microelectrode arrays, electrosynthesis, and the optimization of signaling on an inert, stable surface
Beilstein J. Org. Chem. 2022, 18, 1488–1498, doi:10.3762/bjoc.18.156
- complex molecule, the synthesis of a complex, two-dimensional addressable surface requires a new type of selectivity – "site-selectivity". The use of electrosynthesis is essential for obtaining this selectivity. With the substrate on the surface of the array, a hydroquinone/quinone redox couple was then
A one-pot electrochemical synthesis of 2-aminothiazoles from active methylene ketones and thioureas mediated by NH4I
Beilstein J. Org. Chem. 2022, 18, 1249–1255, doi:10.3762/bjoc.18.130
- , the in situ generated α-iodoketone was proposed to be the key active species. Keywords: 2-aminothiazoles; electrosynthesis; indirect electrolysis; halide ion; Introduction Thiazoles are prevalent structural motifs in a wide range of natural products [1] and synthetic molecules possessing various
- . Organic electrosynthesis has been recognized as a green, modern, and safe technique, since electrons can be used as an alternative for oxidants or reductants [30][31][32][33][34][35][36][37][38]. During our continuous interests in halide-mediated indirect electrolysis [39][40][41][42], we have achieved
Reductive opening of a cyclopropane ring in the Ni(II) coordination environment: a route to functionalized dehydroalanine and cysteine derivatives
Beilstein J. Org. Chem. 2022, 18, 1166–1176, doi:10.3762/bjoc.18.121
- base complexes; stereoselective electrosynthesis; voltammetric testing; Introduction Electrochemistry provides a direct access to highly reactive species by means of harnessing electrons or electron holes as reagents [1][2]. This capacity can be efficiently exploited in organic synthesis for rational
Electro-conversion of cumene into acetophenone using boron-doped diamond electrodes
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
- straightforward electro-conversion of cumene into acetophenone using boron-doped diamond (BDD) electrodes. The BDD’s wide potential window enabled the direct anodic oxidation of cumene to afford a key reaction intermediate, which cannot be realized by other electrodes such as graphite and Ni. Electrosynthesis is
Electrochemical vicinal oxyazidation of α-arylvinyl acetates
Beilstein J. Org. Chem. 2022, 18, 1026–1031, doi:10.3762/bjoc.18.103
- diverse α-azidoketones in good yields without the use of a stoichiometric amount of chemical oxidant. A range of functionality is shown to be compatible with this transformation, and further applications are demonstrated. Keywords: azide; azidoketone; electrosynthesis; enol acetate; radical
- have reported a manganese dioxide-catalyzed radical azidation of enol acetates to afford the corresponding azidoketones using dioxygen as the oxidant (Scheme 1A) [14]. The adoption of electrosynthesis in green and sustainable redox transformations has been experiencing a dynamic renaissance [15][16][17
First example of organocatalysis by cathodic N-heterocyclic carbene generation and accumulation using a divided electrochemical flow cell
Beilstein J. Org. Chem. 2022, 18, 979–990, doi:10.3762/bjoc.18.98
- 1,3-diketones [21], etc. Electrosynthesis is considered as a more sustainable approach to perform chemical reactions, and an interesting alternative to conventional synthetic methods both in laboratory and industry processes. In fact, the electron may be considered to be a clean reagent, which
- replaces toxic chemical redox reagents and dangerous procedures [22][23][24][25]. At present, electrosynthesis in batch is more widely used and reported in literature, but some disadvantages can be encountered: the need for high concentrations of supporting electrolyte, poor performance for synthesis such
- at the cathode is usually H2 evolution [29]. The use of divided cells is less common in organic electrosynthesis, mainly due to complications inherent with membranes. Useful cathodic processes are less exploited in organic electrochemistry. In the context of NHC organocatalysis in flow
Synthesis of piperidine and pyrrolidine derivatives by electroreductive cyclization of imine with terminal dihaloalkanes in a flow microreactor
Beilstein J. Org. Chem. 2022, 18, 350–359, doi:10.3762/bjoc.18.39
- , organic electrosynthetic reactions, which are driven by direct electron transfer to and from the electrodes, can produce highly reactive species under ambient conditions without the use of harmful and precious chemicals. Therefore, electrosynthesis has been actively researched in recent years as a green
- introduced to the microreactor by a syringe pump (KDS100, KdScientific Muromachi Kikai) during the electrosynthesis. Electroreductive cyclization was conducted using a potentiogalvanostat (HABF-501A, Hokuto Denko). High-performance liquid chromatography (HPLC) analysis for 3a and 4 was performed with a
Electrocatalytic C(sp3)–H/C(sp)–H cross-coupling in continuous flow through TEMPO/copper relay catalysis
Beilstein J. Org. Chem. 2021, 17, 2650–2656, doi:10.3762/bjoc.17.178
- for electrosynthesis and have been employed to reduce the use of supporting electrolyte, facilitate reaction scale-up, and increase reaction efficiency [20][21][22][23][24][25][26][27][28][29][30][31][32]. Despite these advantages of continuous-flow electrosynthesis and the intense interests in
- transition-metal electrocatalysis [33][34][35][36][37][38][39], transition-metal electrocatalysis in continuous flow remains underexplored [40]. With our continued interests in transition-metal electrocatalysis [41][42] and continuous-flow electrosynthesis [43][44][45][46][47][48], we report herein the
- electrosynthesis was conducted in a microreactor equipped with two Pt electrodes as the anode and cathode and operated with a constant current (Table 1). Under the optimized conditions, a solution of tetrahydroisoquinoline 1a (1 equiv), alkyne 2 (1.5 equiv), Cu(OTf)2 (10 mol %), TEMPO (20 mol %), n-Bu4NPF6 (0.2
On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets
Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126
- in the azidation of inert C(sp3)–H bonds using organic electrosynthesis in a straightforward procedure, enabling the azidation of a series of primary, secondary and tertiary alkyl moieties (Scheme 22B and C) [144]. In general, the new methodology proved to be resource-economic and straightforward
- retinoic acid receptor agonist analogue 63 and an estrone acetate derivative 64 (Scheme 22D). A seminal work involving manganese-catalyzed C–H organic electrosynthesis and photoredox catalysis was reported in the same year by Lei and co-workers, also regarding the azidation of alkyl scaffolds (Scheme 23A
When metal-catalyzed C–H functionalization meets visible-light photocatalysis
Beilstein J. Org. Chem. 2020, 16, 1754–1804, doi:10.3762/bjoc.16.147
- –H activations, visible-light-induced photocatalysis, electrosynthesis, enzyme catalysis, and others. Each of these techniques aims at accessing complex molecules while limiting ecological footprint. Over the last decade, the metal-catalyzed C–H activation established itself as one of the most
A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions
Beilstein J. Org. Chem. 2019, 15, 2710–2746, doi:10.3762/bjoc.15.264
- redox mediators, electroauxiliaries, supporting electrolyte, types of catalysts; and many other controlling factors [5][6][7]. The complex history of organic electrosynthesis has been revisited in detail in a number of articles [8][9][10][11][12]. The two sequential reviews from Baran’s group and
- Waldvogel’s group focused on the advancements achieved in the development of synthetic methods as well as applications of organic electrosynthesis reported since 2000 [13][14]. Moreover, in his recent article, Moeller have nicely demonstrated that both physical and organic chemistry are indispensable for
- methods can be achieved by using suitable chiral sources [16]. Several groups of organic chemists have been involved in establishing and improving the effectiveness of chiral inductors for electrosynthesis; as a result, a number of reports have been published in this important field of synthetic organic
A diastereoselective approach to axially chiral biaryls via electrochemically enabled cyclization cascade
Beilstein J. Org. Chem. 2019, 15, 795–800, doi:10.3762/bjoc.15.76
- the electrosynthesis was investigated by varying the peripheral substituents of the carbamate substrate 2 (Scheme 2). The pyridyl ring could be substituted at positions 4, 5 and 6 with a range of substituents with diverse electronic properties such as OMe (3e), Br (3f), CF3 (3g), CN (3h), Cl (3i), and
Cobalt–metalloid alloys for electrochemical oxidation of 5-hydroxymethylfurfural as an alternative anode reaction in lieu of oxygen evolution during water splitting
Beilstein J. Org. Chem. 2018, 14, 1436–1445, doi:10.3762/bjoc.14.121
- with the same electrode. Electrolysis of HMF using a CoB modified nickel foam electrode at 1.45 V vs RHE achieved close to 100% selective conversion of HMF to FDCA at 100% faradaic efficiency. Keywords: alternative anode reaction; electrocatalysis; electrosynthesis; HMF oxidation; hydrogen evolution
Spectroelectrochemical studies on the effect of cations in the alkaline glycerol oxidation reaction over carbon nanotube-supported Pd nanoparticles
Beilstein J. Org. Chem. 2018, 14, 1428–1435, doi:10.3762/bjoc.14.120
- complicates the total oxidation reaction, because numerous intermediates occur that need to be oxidized efficiently without poisoning the catalyst. Another important utilization of glycerol is the electrosynthesis of fine chemicals. It is a highly suitable precursor for valuable chemicals such as DL-glyceric
- biopolymers like polyesters and polyurethanes [4]. The route to higher functionalized products starting from glycerol via electrosynthesis offers several advantages compared with thermal gas-phase oxidation processes. In the aqueous environment low temperatures and pressures are applied allowing a higher
- in the electrolyte by blocking surface sites that are required for the carbon bond cleavage. To the best of our knowledge, there are no studies focusing on the cation effect on the glycerol electrooxidation reaction using Pd-based materials. With respect to FC applications and the electrosynthesis of
Polysubstituted ferrocenes as tunable redox mediators
Beilstein J. Org. Chem. 2018, 14, 1004–1015, doi:10.3762/bjoc.14.86
- electrosynthesis. Keywords: cyclic voltammetry; ferrocene; paramagnetic NMR spectroscopy; redox mediator; spectroelectrochemistry; Introduction Since its discovery, ferrocene (FcH) has been established as versatile redox-active building block [1][2][3]. Ferrocene can be reversibly oxidized to the 17 valence
Electrochemically modified Corey–Fuchs reaction for the synthesis of arylalkynes. The case of 2-(2,2-dibromovinyl)naphthalene
Beilstein J. Org. Chem. 2018, 14, 891–899, doi:10.3762/bjoc.14.76
- in the previous paper) [25]. In order to ascertain the role of the solvent in this electrosynthesis, we carried out an electrolysis in DMF instead of ACN on a Pt cathode at the controlled potential of −2.00 V vs SCE, corresponding to the first reduction wave of 1a (Table 1, entry 2). The current flow
- influence the outcome of an electrosynthesis, so we carried out electrolyses of 1a using a glassy carbon cathode (Table 1, entry 8) and a silver cathode (Table 1, entry 9). In both cases the working potential was that of the first reduction wave. In the case of glassy carbon, the electrolysis could not be
- electrode material. This voltammetric analysis shows that the cathodic reduction of both 1a and 3a could lead to the formation of the desired alkyne 2a. To ascertain this hypothesis and to get information on the nature of the intermediates of the electrochemical process, we carried out the electrosynthesis
Electrochemical Corey–Winter reaction. Reduction of thiocarbonates in aqueous methanol media and application to the synthesis of a naturally occurring α-pyrone
Beilstein J. Org. Chem. 2018, 14, 547–552, doi:10.3762/bjoc.14.41
- -(pent-1-enyl)-α-pyrone and trans-6-(pent-1,4-dienyl)-α-pyrone, which are naturally occurring metabolites isolated from Trichoderma viride and Penicillium, in high chemical yield and with excellent stereo selectivity. Keywords: Corey–Winter reaction; electrosynthesis; 6-pentyl-2H-pyran-2-ones; reduction
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