Recent developments in photoredox-catalyzed remote ortho and para C–H bond functionalizations

• Rafia Siddiqui and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 248–280, doi:10.3762/bjoc.16.26

• in this vital area of research, to our best knowledge, this is the first review that focuses on ortho and para C–H functionalizations by photoredox catalysis to provide atom- and step-economic organic transformations. We are certain that this review will act as a promoter to highlight the application

A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

• Munmun Ghosh,
• Valmik S. Shinde and
• Magnus Rueping

Beilstein J. Org. Chem. 2019, 15, 2710–2746, doi:10.3762/bjoc.15.264

• Munmun Ghosh Valmik S. Shinde Magnus Rueping KAUST Catalysis Center (KCC), King Abdullah University of Science and Technology, Thuwal 23955-6900, Saudi Arabia 10.3762/bjoc.15.264 Abstract The direct exploitation of ‘electrons’ as reagents in synthetic organic transformations is on the verge of a

• sequences, these strategies enable advancements in reaction scalability as well as tunability. Having described the research that has been conducted to achieve suitable ‘electrical’ replacements of conventional ‘chemical’ organic transformations, it is clear that the establishment of stereoselective

Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups

• Xiaowei Li,
• Xiaolin Shi,
• Xiangqian Li and
• Dayong Shi

Beilstein J. Org. Chem. 2019, 15, 2213–2270, doi:10.3762/bjoc.15.218

• a prevalent catalyst in a huge number of organic transformations. Similar to palladium complexes, copper complexes generally exist in four oxidation states, Cu(0), Cu(I), Cu(II), and Cu(III) and various fluorination reactions could be developed by different catalytic mechanisms. Fluorination of

Naphthalene diimides with improved solubility for visible light photoredox catalysis

• Barbara Reiß and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2019, 15, 2043–2051, doi:10.3762/bjoc.15.201

• conclusively showed that there is no universal photoredox catalyst for different organic transformations. Instead, each photoredox catalyst has its own reactivity profile and scope. In order to apply organic dyes in advanced photoredox catalysts in a versatile way, it is crucial that modifications can be

Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage

• Gagandeep Kour Reen,
• Ashok Kumar and
• Pratibha Sharma

Beilstein J. Org. Chem. 2019, 15, 1612–1704, doi:10.3762/bjoc.15.165

• (Scheme 8). Heterogenization of organic catalysts on Fe3O4 NPs has attracted much attention as these catalysts can be recovered by an external magnetic field and reused in subsequent reactions. Some metal complexes of 2,2-biimidazole (H2Biim) found to be effective catalysts in many organic transformations

• the use of toxic reagents and solvents, harsh reaction conditions and long reaction times. The use of a heterogeneous catalyst and water made this method a green and sustainable approach for organic transformations. This transformation involved the well known three-component reaction of 3 with 1 and 2

• copper catalyst dissolved in ionic liquid to four synthetic cycles. Nanotechnology coupled with heterogeneous catalysis has emerged as an efficient field of catalysis for various organic transformations. Inspired from this Bagdi et al. have reported a nano-copper oxide-mediated three-component A3

A heteroditopic macrocycle as organocatalytic nanoreactor for pyrroloacridinone synthesis in water

• Piyali Sarkar,
• Sayan Sarkar and
• Pradyut Ghosh

Beilstein J. Org. Chem. 2019, 15, 1505–1514, doi:10.3762/bjoc.15.152

• summary, a multifunctional heteroditopic macrocycle is established as an efficient nanoreactor for organic transformations in water. Using this macrocycle, a library of biologically interesting highly substituted pyrroloacridines has been synthesized with high yields from easily available starting

• aggregation tendency. Herein we have extensively explored a multifunctional macrocycle (BATA-MC), comprising bis-amide and tris-amine functionalities as H-bond donor/acceptor moieties, and parallel benzene moieties for aromatic π–π stacking interactions as an organocatalytic nanoreactor for organic

• transformations, in particular, for the synthesis of biologically important highly substituted pyrroloacridines in the ecofriendly solvent water. Results and Discussion Synthesis of the macrocycle Considerable efforts in synthesizing multifunctional macrocycles have been dedicated lately for the construction of

Mechanochemistry of supramolecules

• Anima Bose and
• Prasenjit Mal

Beilstein J. Org. Chem. 2019, 15, 881–900, doi:10.3762/bjoc.15.86

• practiced in supramolecular chemistry to produce complex molecules with topological diversity [81]. Therefore, organic transformations through subcomponent synthesis under mechano-milling conditions might be considered as a useful tool for performing a chemical reaction in a greener fashion. The

Oxidative radical ring-opening/cyclization of cyclopropane derivatives

• Yu Liu,
• Qiao-Lin Wang,
• Zan Chen,
• Cong-Shan Zhou,
• Bi-Quan Xiong,
• Pan-Liang Zhang,
• Chang-An Yang and
• Quan Zhou

Beilstein J. Org. Chem. 2019, 15, 256–278, doi:10.3762/bjoc.15.23

• several decades [39][40][41][42]. The free radical reaction was applied in a range of organic transformations because of its unique advantages such as excellent reactivity, mild conditions, functional group tolerance, and atom economy. A series of radicals, such as carbon, Se, CF3, halogen, S and N

Copolymerization of epoxides with cyclic anhydrides catalyzed by dinuclear cobalt complexes

• Yo Hiranoi and
• Koji Nakano

Beilstein J. Org. Chem. 2018, 14, 2779–2788, doi:10.3762/bjoc.14.255

• methods [22][23][24][25][26]. Cooperative dinuclear metal catalysts have been considered as a promising design for high activity and/or selectivity in organic transformations including polymerizations [27][28][29][30]. This was found to be true for the epoxide/CA copolymerization. In 2013, Lu and co

An overview on recent advances in the synthesis of sulfonated organic materials, sulfonated silica materials, and sulfonated carbon materials and their catalytic applications in chemical processes

• Hashem Sharghi,
• Pezhman Shiri and
• Mahdi Aberi

Beilstein J. Org. Chem. 2018, 14, 2745–2770, doi:10.3762/bjoc.14.253

• handling, and even reusability [34]. Ionic liquids (ILs) have been extensively reported as green solvents in organic transformations, owing to their considerable properties such as the ability to dissolve a wide range of substances, very low vapor pressure, high thermal stability, recyclability, non

Learning from B₁₂ enzymes: biomimetic and bioinspired catalysts for eco-friendly organic synthesis

• Keishiro Tahara,
• Ling Pan,
• Toshikazu Ono and
• Yoshio Hisaeda

Beilstein J. Org. Chem. 2018, 14, 2553–2567, doi:10.3762/bjoc.14.232

• reductases to B12 was replaced with that from the cathodes to B12 derivatives [43]. Light-driven organic transformations attract great attention due to their relevance to photosynthesis in nature as an ideal sustainable system [92][93][94]. In this context, we constructed light-driven catalytic systems using

Catalyst-free synthesis of 4-acyl-NH-1,2,3-triazoles by water-mediated cycloaddition reactions of enaminones and tosyl azide

• Lu Yang,
• Yuwei Wu,
• Yiming Yang,
• Chengping Wen and
• Jie-Ping Wan

Beilstein J. Org. Chem. 2018, 14, 2348–2353, doi:10.3762/bjoc.14.210

• adventure in enaminone-based organic transformations has led us to the discovery that the cycloaddition of N,N-dimethylenaminones and tosyl azide efficiently affords NH-1,2,3-triazoles with water as the only medium, and not any catalyst or additive is required. Considering the featured functions of NH-1,2,3

Hydroarylations by cobalt-catalyzed C–H activation

• Rajagopal Santhoshkumar and
• Chien-Hong Cheng

Beilstein J. Org. Chem. 2018, 14, 2266–2288, doi:10.3762/bjoc.14.202

• Rajagopal Santhoshkumar Chien-Hong Cheng Department of Chemistry, National Tsing Hua University, Taiwan 10.3762/bjoc.14.202 Abstract As an earth-abundant first-row transition metal, cobalt catalysts offer a broad range of economical methods for organic transformations via C–H activation. One of

Cobalt-catalyzed C–H cyanations: Insights into the reaction mechanism and the role of London dispersion

• Eric Detmar,
• Valentin Müller,
• Daniel Zell,
• Lutz Ackermann and
• Martin Breugst

Beilstein J. Org. Chem. 2018, 14, 1537–1545, doi:10.3762/bjoc.14.130

• – the attractive part of the van-der-Waals interaction – is known for more than 100 years [1][2]. The stabilizing nature of C–H···H–C interactions and their importance for organic transformations has only been fully realized within the last decades [3]. Among others, these interactions explain the

A survey of chiral hypervalent iodine reagents in asymmetric synthesis

• Soumen Ghosh,
• Suman Pradhan and
• Indranil Chatterjee

Beilstein J. Org. Chem. 2018, 14, 1244–1262, doi:10.3762/bjoc.14.107

• of an external oxidant. The use of catalytic chiral hypervalent iodine reagents in asymmetric catalysis is one of the most challenging ongoing topics and this review will focus on the development of various chiral hypervalent iodine reagents and their application in typical organic transformations

• substantial growth in the field of chiral hypervalent iodine reagents. This review points a number of striking chiral hypervalent iodine reagents used in stoichiometric or in catalytic fashion for quite a number of useful organic transformations. Most importantly the oxidative chemistry can be done using

Sequential Ugi reaction/base-induced ring closing/IAAC protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins

• Robby Vroemans,
• Fante Bamba,
• Jonas Winters,
• Joice Thomas,
• Jeroen Jacobs,
• Luc Van Meervelt,
• Jubi John and
• Wim Dehaen

Beilstein J. Org. Chem. 2018, 14, 626–633, doi:10.3762/bjoc.14.49

• accessed by designing sequential organic transformations incorporating multicomponent reactions [1][2] combined with secondary transformations [3][4][5][6][7][8][9][10][11]. Over the past decade, several groups of chemists interested in synthetic chemistry have efficiently utilized the strategy of linking

An air-stable bisboron complex: a practical bidentate Lewis acid catalyst

• Longcheng Hong,
• Sebastian Ahles,
• Andreas H. Heindl,
• Gastelle Tiétcha,
• Andrey Petrov,
• Zhenpin Lu,
• Christian Logemann and
• Hermann A. Wegner

Beilstein J. Org. Chem. 2018, 14, 618–625, doi:10.3762/bjoc.14.48

• ) reaction of 1,2-diazine as well as 1,2,4,5-tetrazine. Its stability towards air and moisture was demonstrated by NMR studies enabling its application in organic transformations without glovebox. A one-pot procedure for its synthesis was developed starting from 1,2-bis(trimethylsilyl)benzene greatly

5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines

• Ranjana Aggarwal and
• Suresh Kumar

Beilstein J. Org. Chem. 2018, 14, 203–242, doi:10.3762/bjoc.14.15

Gram-scale preparation of negative-type liquid crystals with a CF₂CF₂-carbocycle unit via an improved short-step synthetic protocol

• Tatsuya Kumon,
• Shohei Hashishita,
• Takumi Kida,
• Shigeyuki Yamada,
• Takashi Ishihara and
• Tsutomu Konno

Beilstein J. Org. Chem. 2018, 14, 148–154, doi:10.3762/bjoc.14.10

• steps less than the previous method. In addition, the present synthetic protocol involves several standard organic transformations, such as hydrogenation and dehydration, which are advantageous for a large-scale synthesis of the target compounds. Thus, we attempted a detailed examination of the short

Photocatalytic formation of carbon–sulfur bonds

• Alexander Wimmer and
• Burkhard König

Beilstein J. Org. Chem. 2018, 14, 54–83, doi:10.3762/bjoc.14.4

• organic transformations, but also limits the scope of this method. Using 3,7-bis(biphenyl-4-yl)-10-(1-naphthyl)phenoxazine as organic photocatalyst instead of [Ir(dF(CF3)ppy)2(dtbbpy)]PF6, Miyake found out that also aryl bromides could be cross-coupled with a series of different thiols. These were not

Electron-deficient pyridinium salts/thiourea cooperative catalyzed O-glycosylation via activation of O-glycosyl trichloroacetimidate donors

• Mukta Shaw,
• Yogesh Kumar,
• Rima Thakur and
• Amit Kumar

Beilstein J. Org. Chem. 2017, 13, 2385–2395, doi:10.3762/bjoc.13.236

• acceleration of many important biochemical reactions, such as glycosyltransferase reactions, hydrolysis of strong amide bonds and others [11][12][13]. Taking inspiration from nature, in the last few decades chemists around the world have utilized organic molecules to accelerate many imperative organic

• transformations [14][15][16][17]. One of the major applications of organocatalysis lies in the field of enantioselective synthesis, where organocatalysts are considered as fundamental tools in the catalysis toolbox [18][19][20][21][22]. Moreover, the reactivity and selectivity of organocatalysts can be further

Solvent-free and room temperature synthesis of 3-arylquinolines from different anilines and styrene oxide in the presence of Al₂O₃/MeSO₃H

• Hashem Sharghi,
• Mahdi Aberi,
• Mohsen Khataminejad and
• Pezhman Shiri

Beilstein J. Org. Chem. 2017, 13, 1977–1981, doi:10.3762/bjoc.13.193

• MeSO3H has been previously used as an effective and mild reagent for organic transformations [14]. In continuation of our studies to develop new synthetic methods for heterocycles [15][16][17][18][19], herein, we disclose a novel route to the synthesis of 3-arylquinolines from aniline derivatives and

Sustainable synthesis of 3-substituted phthalides via a catalytic one-pot cascade strategy from 2-formylbenzoic acid with β-keto acids in glycerol

• Lina Jia and
• Fuzhong Han

Beilstein J. Org. Chem. 2017, 13, 1425–1429, doi:10.3762/bjoc.13.139

• , as an environmentally friendly reaction medium, has received increasing interest for organic reactions because of its peculiar physical and chemical properties such as polarity, low toxicity, biodegradability, high boiling point, and ready availability from renewable feed stocks [31]. Many organic

• transformations have been accomplished using glycerol as a solvent [32][33][34][35][36][37][38][39][40]. Therefore, as part of our ongoing research interest in exploring novel and sustainable transformations of β-keto acids [41][42], we envisioned that the direct utilization of β-keto acids as nucleophilic

Pd- and Cu-catalyzed approaches in the syntheses of new cholane aminoanthraquinone pincer-like ligands

• Nikolay V. Lukashev,
• Gennadii A. Grabovyi,
• Dmitry A. Erzunov,
• Alexey V. Kazantsev,
• Gennadij V. Latyshev,
• Alexei D. Averin and
• Irina P. Beletskaya.

Beilstein J. Org. Chem. 2017, 13, 564–570, doi:10.3762/bjoc.13.55

• serve as sensors for aromatic compounds [24]. During the first decade of the XXI century, the main approaches to cyclic and pincer cholane derivatives were based on “classical” organic transformations (acylation, alkylation, etc.) [7][8][25][26][27]. Later, two modern synthetic approaches based on metal

Extrusion – back to the future: Using an established technique to reform automated chemical synthesis

• Deborah E. Crawford

Beilstein J. Org. Chem. 2017, 13, 65–75, doi:10.3762/bjoc.13.9

• compounds including metal-organic frameworks (MOFs). To date, a vast amount of research has already been conducted into reactive extrusion (REX), particularly in the polymer industry, which in many cases has involved organic transformations, however, it has not received significant recognition for this

• large quantities of materials in the range of tonnes per hour as a result of the extensive engineering research. Herein, a focused discussion of the reactive processes carried out by extrusion is provided. A substantial amount of the organic transformations carried out by extrusion has been in the

• extensive amount of research into continuous organic transformations by extrusion and encourage them to consider the potential that extrusion holds for continuous chemical synthesis, particularly under solvent-free conditions. Reactive extrusion (REX) Extrusion is employed most frequently in the polymer