Advances in radical peroxidation with hydroperoxides

• Oleg V. Bityukov,
• Pavel Yu. Serdyuchenko,
• Andrey S. Kirillov,
• Gennady I. Nikishin,
• Vera A. Vil’ and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2024, 20, 2959–3006, doi:10.3762/bjoc.20.249

• compounds (β-diketones, β-ketoesters, and malonic esters) with TBHP via homogeneous and heterogeneous Cu(II)-catalysis were developed (Scheme 10) [45][46][47]. It was assumed that the reaction pathway includes the formation of diketonate complex A from β-dicarbonyl compound 19 and copper(II) salt, which

A photochemical C=C cleavage process: toward access to backbone N-formyl peptides

• Haopei Wang and
• Zachary T. Ball

Beilstein J. Org. Chem. 2021, 17, 2932–2938, doi:10.3762/bjoc.17.202

• ) provide entry into similar photo-uncaging chemistries for amide release. Figure 1C shows an example of this concept applied to a peptide substrate. Reaction of the peptide i with an alkenylboronic acid reagent iv in the presence of a copper(II) salt in water provides access to the backbone N–H

Oxime radicals: generation, properties and application in organic synthesis

• Igor B. Krylov,
• Stanislav A. Paveliev,
• Alexander S. Budnikov and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2020, 16, 1234–1276, doi:10.3762/bjoc.16.107

Copper-catalyzed asymmetric sp³ C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst

• Pierre Querard,
• Inna Perepichka,
• Eli Zysman-Colman and
• Chao-Jun Li

Beilstein J. Org. Chem. 2016, 12, 2636–2643, doi:10.3762/bjoc.12.260

• toluene and THF (Table 1, entries 7 and 8). On the other hand, highly polar solvents such as MeCN and MeOH were not beneficial for the formation of the desired product 3a (Table 1, entries 9 and 10). Control experiments performed in the absence of photoredox catalyst and/or transition metal copper(II

• ) salt (Table 1, entries 11–13) showed very poor reactivity. Moreover, in the absence of light, an extremely poor yield was obtained (Table 1, entry 14). General scope of reaction With the optimized reaction conditions in hand, the substrate scope was investigated (Figure 1). N

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

• process (Scheme 12). In the presence of a Cu(II) catalyst, the one-electron oxidation to the phenol led to the occurrence of phenoxy radical 25 via the formation of phenoxyl copper(II) salt 24. The isomeric free radical species 26 then rapidly captured the halogen atom from LiX to give the target product

Recent advances in transition metal-catalyzed Csp²-monofluoro-, difluoro-, perfluoromethylation and trifluoromethylthiolation

• Grégory Landelle,
• Armen Panossian,
• Sergiy Pazenok,
• Jean-Pierre Vors and
• Frédéric R. Leroux

Beilstein J. Org. Chem. 2013, 9, 2476–2536, doi:10.3762/bjoc.9.287

• ]thiazoles, imidazoles and polyfluorobenzenes (same system but di-tert-butyl peroxide as oxidant instead of air, Table 21); the nature of the copper(II) salt, the base and the oxidant had to be reassessed for the reaction of indoles (Cu(OH)2/1,10-phenanthroline/KF/Ag2CO3). Interestingly, the results obtained

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

• Eietsu Hasegawa Minami Tateyama Ryosuke Nagumo Eiji Tayama Hajime Iwamoto Department of Chemistry, Faculty of Science, Niigata University, Ikarashi-2 8050, Niigata 950-2181, Japan 10.3762/bjoc.9.156 Abstract Copper(II)-salt-promoted oxidative ring-opening reactions of bicyclic cyclopropanol

• proposed. Keywords: copper(II) salt; cyclopropanol; electron transfer; free radical; radical ion probe; Introduction Radical ions are key intermediates in electron-transfer (ET) reactions of organic molecules [1][2][3][4][5] and they often undergo fragmentations to yield free radicals and ions [6][7][8

• (II)-salt-promoted oxidative ring-opening reactions of selected bicyclic cyclopropanol derivatives. Results and Discussion In the initial phase of this effort, we examined the reaction of cyclopropyl silyl ether 1a (0.40 mmol) with copper(II) acetate, Cu(OAc)2 , (1.1 equiv) for 1 h at room temperature

Palladium-catalyzed dual C–H or N–H functionalization of unfunctionalized indole derivatives with alkenes and arenes

• Gianluigi Broggini,
• Egle M. Beccalli,
• Andrea Fasana and
• Silvia Gazzola

Beilstein J. Org. Chem. 2012, 8, 1730–1746, doi:10.3762/bjoc.8.198

• requires an oxidation by the copper(II) salt to the Pd(II) species, which is then suitable to restart a new catalytic cycle. Recently, the oxidative Pd(II)-catalyzed strategy for the cyclization of alkenylindoles has been extended to the intramolecular domino reactions of indolylallylamides by using the