Investigating radical cation chain processes in the electrocatalytic Diels–Alder reaction

• Yasushi Imada,
• Yohei Okada and
• Kazuhiro Chiba

Beilstein J. Org. Chem. 2018, 14, 642–647, doi:10.3762/bjoc.14.51

• solution. We assumed that the catalytic efficiency of the reaction would be further improved through optimizing and/or tuning the conditions in order to facilitate the bulk SET processes. As recently demonstrated by Baran [27][28] and Waldvogel [29][30], electrochemical synthesis has also proven to be

• highly scalable as well as sustainable. The longer chain length, also referred to as a higher “current efficiency” in this context, would enhance such advantages of the electrochemical synthesis. It should also be noted that the mechanism of electrochemical reactions can easily be studied since the

• electrochemical synthesis in that one electron can run the radical cation chain process up to 65 times. GC–MS monitoring showed a sigmoidal curve with an induction period. The monitoring was carried out in the presence of a large excess (10 equivalents) of isoprene (2), which might follow pseudo-first order

Vinylphosphonium and 2-aminovinylphosphonium salts – preparation and applications in organic synthesis

• Anna Kuźnik,
• Roman Mazurkiewicz and
• Beata Fryczkowska

Beilstein J. Org. Chem. 2017, 13, 2710–2738, doi:10.3762/bjoc.13.269

• aldehydes. Synthesis of 1-cycloalkenetriphenylphosphonium salts by electrochemical oxidation of triphenylphosphine in the presence of cycloalkenes. Suggested mechanism for the electrochemical synthesis of 1-cycloalkenetriphenylphosphonium salts. Generation of α,β-(dialkoxycarbonyl)vinylphosphonium salts by

An effective Pd nanocatalyst in aqueous media: stilbene synthesis by Mizoroki–Heck coupling reaction under microwave irradiation

• Carolina S. García,
• Paula M. Uberman and
• Sandra E. Martín

Beilstein J. Org. Chem. 2017, 13, 1717–1727, doi:10.3762/bjoc.13.166

• reactions has been reported, using a phase-transfer agent and focusing on the employment of ultralow catalyst concentrations [45]. Recently, we reported the electrochemical synthesis of stable Pd NPs by using platinum or vitreous carbon electrodes at room temperature via direct electroreduction of aqueous

• . Synthesis of Pd nanoparticles suspension by electrochemical reduction The electrochemical synthesis of PVP-Pd NPs was carried out as previously reported [46]. The experiments were achieved in a glass electrochemical cell equipped with a Pt disc working electrode (geometric area = 0.0746 cm2), a very large

C–H bond halogenation catalyzed or mediated by copper: an overview

• Wenyan Hao and
• Yunyun Liu

Beilstein J. Org. Chem. 2015, 11, 2132–2144, doi:10.3762/bjoc.11.230

• -workers [71] successfully achieved the selective mono-α-chlorination of β-keto esters/amides and 1,3-diketone 78 by employing an electrochemical synthesis via a catalysis by means of Cu(OTf)2. The synthesis of chlorinated carbonyl products 79 were acquired in a divided cell using aqueous HCl as chlorine

A new approach to ferrocene derived alkenes via copper-catalyzed olefination

• Vasily M. Muzalevskiy,
• Aleksei V. Shastin,
• Alexandra D. Demidovich,
• Namiq G. Shikhaliev,
• Abel M. Magerramov,
• Victor N. Khrustalev,
• Rustem D. Rakhimov,
• Sergey Z. Vatsadze and
• Valentine G. Nenajdenko

Beilstein J. Org. Chem. 2015, 11, 2072–2078, doi:10.3762/bjoc.11.223

• current values of oxidation at the iron atom. These findings allow us to state that the synthesized molecules are promising starting materials for the electrochemical synthesis of ferrocene-containing conjugated polymers. Conclusion In conclusion, a novel stereoselective route to ferrocenyl haloalkenes

IR and electrochemical synthesis and characterization of thin films of PEDOT grown on platinum single crystal electrodes in [EMMIM]Tf₂N ionic liquid

• Andrea P. Sandoval,
• Marco F. Suárez-Herrera and
• Juan M. Feliu

Beilstein J. Org. Chem. 2015, 11, 348–357, doi:10.3762/bjoc.11.40

• electrochemical synthesis of PEDOT. The electrochemical properties of thin films of PEDOT are subsequently studied and compared with the behavior obtained in acetonitrile. Results and Discussion Cyclic voltammetry Figure 1 shows the cyclic voltammograms of EDOT in [EMMIM]Tf2N. The onset of the EDOT oxidation

Stereoselective cathodic synthesis of 8-substituted (1R,3R,4S)-menthylamines

• Carolin Edinger,
• Jörn Kulisch and
• Siegfried R. Waldvogel

Beilstein J. Org. Chem. 2015, 11, 294–301, doi:10.3762/bjoc.11.34

• electrochemical preparation of 8a. Electrochemical synthesis of 12a using different additives. Influence of the concentration of additive 11 on the electroreduction of 7b. Supporting Information Supporting Information File 76: Experimental details and 1H and 13C NMR spectra are provided. Acknowledgements

3α,5α-Cyclocholestan-6β-yl ethers as donors of the cholesterol moiety for the electrochemical synthesis of cholesterol glycoconjugates

• Aneta M. Tomkiel,
• Adam Biedrzycki,
• Jolanta Płoszyńska,
• Dorota Naróg,
• Andrzej Sobkowiak and
• Jacek W. Morzycki

Beilstein J. Org. Chem. 2015, 11, 162–168, doi:10.3762/bjoc.11.16

• /bjoc.11.16 Abstract 3α,5α-Cyclocholestan-6β-yl alkyl and aryl ethers were proved to be efficient cholesteryl donors in the electrochemical synthesis of glycoconjugates. 3α,5α-Cyclocholestan-6β-ol (i-cholesterol) and its tert-butyldimethylsilyl ether can also be used for this purpose. The i-cholesterol

• during electrochemical oxidation by cleavage of the carbon–oxygen bond in an intermediate radical-cation. For this reason, i-cholesteryl ethers seemed to be suitable donors of the cholesterol moiety for the electrochemical synthesis of cholesterol glycoconjugates. A series of i-cholesterol derivatives 6b

• ethers 6a–h is necessary for their reactions with sugar 7. No coupling occurred when chemical promoters were attempted. Conclusion 3α,5α-Cyclocholestan-6β-yl ethers are excellent cholesteryl donors for the electrochemical synthesis of cholesterol glycoconjugates. All of the tested compounds proved

Recent advances in the electrochemical construction of heterocycles

• Robert Francke

Beilstein J. Org. Chem. 2014, 10, 2858–2873, doi:10.3762/bjoc.10.303

• conducted at low temperatures. The electrochemical synthesis of heterocyclic compounds can be considered as a mature discipline. The last comprehensive review dealing with electrochemical heterocycle generation has been published in 1997 by Tabaković [26]. Earlier reviews on different aspects of the

• intermolecular cyclizations Yoshida, Suga and co-workers investigated the electrochemical synthesis of five-membered heterocycles by integration of an intermolecular and an intramolecular step in one sequence. For this purpose, acyl iminium ions, electrogenerated as a cation pool at −78 °C, were converted at −23

• Undoubtedly, much progress has been made in the electrochemical synthesis of heterocyclic compounds since Tabaković's review appeared in 1997. Advances in anodic olefin coupling or electrochemically induced radical cyclization have made important contributions to this field. Moreover, the emergence of the

Electrocarboxylation: towards sustainable and efficient synthesis of valuable carboxylic acids

• Roman Matthessen,
• Jan Fransaer,
• Koen Binnemans and
• Dirk E. De Vos

Beilstein J. Org. Chem. 2014, 10, 2484–2500, doi:10.3762/bjoc.10.260

• , Celestijnenlaan 200F, B-3001 Leuven, Belgium 10.3762/bjoc.10.260 Abstract The near-unlimited availability of CO2 has stimulated a growing research effort in creating value-added products from this greenhouse gas. This paper presents the trends on the most important methods used in the electrochemical synthesis

A practical microreactor for electrochemistry in flow

• Kevin Watts,
• William Gattrell and
• Thomas Wirth

Beilstein J. Org. Chem. 2011, 7, 1108–1114, doi:10.3762/bjoc.7.127

• Kevin Watts William Gattrell Thomas Wirth Cardiff University, School of Chemistry, Park Place, Cardiff CF10 3AT, UK Prosidion Ltd, Watlington Road, Oxford OX4 6LT, UK 10.3762/bjoc.7.127 Abstract A microreactor for electrochemical synthesis has been designed and fabricated. It has been shown that