Synthesis of piperidine and pyrrolidine derivatives by electroreductive cyclization of imine with terminal dihaloalkanes in a flow microreactor

• Yuki Naito,
• Naoki Shida and
• Mahito Atobe

Beilstein J. Org. Chem. 2022, 18, 350–359, doi:10.3762/bjoc.18.39

• and sustainable synthetic method in the face of increasingly stringent environmental and economic constraints. In this context, several groups have demonstrated the electrochemical synthesis of piperidine and pyrrolidine derivatives by anodic oxidation [22][23][24][25][26]. In contrast, there has been

Recent developments and trends in the iron- and cobalt-catalyzed Sonogashira reactions

• Surendran Amrutha,
• Sankaran Radhika and
• Gopinathan Anilkumar

Beilstein J. Org. Chem. 2022, 18, 262–285, doi:10.3762/bjoc.18.31

• using cobalt as additive. Plausible mechanism of Sonogashira cross-coupling reaction over [LaPd*]. (Reproduced with permission from ACS Sustainable Chem. Eng. 2019, 7, 12697–12706.) Funding SR thanks the Kerala State Council for Science Technology and Environment (KSCSTE, Trivandrum) for a research

Multi-faceted reactivity of N-fluorobenzenesulfonimide (NFSI) under mechanochemical conditions: fluorination, fluorodemethylation, sulfonylation, and amidation reactions

• José G. Hernández,
• Karen J. Ardila-Fierro,
• Dajana Barišić and
• Hervé Geneste

Beilstein J. Org. Chem. 2022, 18, 182–189, doi:10.3762/bjoc.18.20

• ; sulfonylation; Introduction Mechanosynthesis of organic molecules and materials using mechanochemical techniques such as ball milling, extrusion, grinding, etc. [1][2][3] have enabled the development of known and new chemical transformations in a more sustainable fashion [4]. Commonly, mechanochemical

• sustainable point of view, experimenting in small scale could prevent waste production and increase safety. However, miniaturization of mechanochemical reactions could also be an alternative to working with precious or expensive reagents and to facilitate monitoring of the reactions [27]. Under such reaction

Earth-abundant 3d transition metals on the rise in catalysis

• Nikolaos Kaplaneris and
• Lutz Ackermann

Beilstein J. Org. Chem. 2022, 18, 86–88, doi:10.3762/bjoc.18.8

• Nikolaos Kaplaneris Lutz Ackermann Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany Wöhler Research Institute for Sustainable Chemistry (WISCh), Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen

• transformations to form C–C and C–heteroatom bonds, thereby providing a more sustainable future for, among others, drug development in generations to come. Particularly, Nobel prize-winning palladium-catalyzed cross-coupling reactions have been recognized by the practitioners in agrochemical and pharmaceutical

• industries as one of the most powerful methods for molecular assembly. With regard to the cost of goods and the allowance of trace metal impurities in medicinally relevant compounds, 3d transition metal complexes, such as those of iron, copper, cobalt or nickel, represent exciting, more sustainable

Efficient N-arylation of 4-chloroquinazolines en route to novel 4-anilinoquinazolines as potential anticancer agents

• Rodolfo H. V. Nishimura,
• Thiago dos Santos,
• Valter E. Murie,
• Luciana C. Furtado,
• Leticia V. Costa-Lotufo and
• Giuliano C. Clososki

Beilstein J. Org. Chem. 2021, 17, 2968–2975, doi:10.3762/bjoc.17.206

• amounts of organic solvents, so it is more sustainable than the protocols reported in the literature. Preliminary screening against selected tumor cells lines (HCT-116, MCF-7, and T98G) demonstrated the medicinal relevance of the 4-anilinoquinazolines synthesized here: many compounds (10b, 10c, 10g, 10k

Polymer chemistry: fundamentals and applications

• Bernhard V. K. J. Schmidt

Beilstein J. Org. Chem. 2021, 17, 2922–2923, doi:10.3762/bjoc.17.200

• , where oligomers bring molecular precision from organic chemistry together with materials properties from polymer chemistry [5]. Especially in the challenge of transformation to a more sustainable polymer science, organic chemistry can give significant support in the development of greener polymer

Iron-catalyzed domino coupling reactions of π-systems

• Austin Pounder and
• William Tam

Beilstein J. Org. Chem. 2021, 17, 2848–2893, doi:10.3762/bjoc.17.196

• catalysts is desirable from both an ecological and economic standpoint. Certainly, in the past couple decades, iron has become a key player in the development of sustainable coupling chemistry and has become an indispensable tool in organic synthesis. Over the last ten years, organic chemistry has witnessed

• production of byproducts. Iron catalysis offers an attractive, and sustainable, approach to the aforementioned economic and ecological concerns. In the same vein, cascade reactions are important tools to meet such challenges currently facing synthetic chemists and have received considerable attention as of

Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

• Umesh P. Aher,
• Dhananjai Srivastava,
• Girij P. Singh and
• Jayashree B. S

Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182

Electrocatalytic C(sp³)–H/C(sp)–H cross-coupling in continuous flow through TEMPO/copper relay catalysis

• Bin Guo and
• Hai-Chao Xu

Beilstein J. Org. Chem. 2021, 17, 2650–2656, doi:10.3762/bjoc.17.178

• and sustainable access to 2-functionalized tetrahydroisoquinolines. Keywords: continuous flow; copper; catalysis; dehydrogenative cross-coupling; electrochemistry; Introduction The dehydrogenative cross-coupling of two C–H bonds represents an ideal strategy for the construction of C–C bonds [1][2

N-Sulfinylpyrrolidine-containing ureas and thioureas as bifunctional organocatalysts

• Viera Poláčková,
• Dominika Krištofíková,
• Boglárka Némethová,
• Renata Górová,
• Mária Mečiarová and
• Radovan Šebesta

Beilstein J. Org. Chem. 2021, 17, 2629–2641, doi:10.3762/bjoc.17.176

• /mismatched combination of chirality, we employed both enantiomers of tert-butyl sulfinamide with the (S)-enantiomer of the pyrrolidine building block. The introduction of green chemistry principles into chemical transformations is an important goal toward sustainable production and manufacturing. Asymmetric

Photoredox catalysis in nickel-catalyzed C–H functionalization

• Lusina Mantry,
• Rajaram Maayuri,
• Vikash Kumar and
• Parthasarathy Gandeepan

Beilstein J. Org. Chem. 2021, 17, 2209–2259, doi:10.3762/bjoc.17.143

• with CO2 is considered an attractive organic synthesis strategy in terms of sustainable aspects [133][134][135]. In 2019, Murakami and co-workers reported on the photoinduced carboxylation of C(sp3)–H bonds with CO2 under 1 atm pressure [136]. Here, the authors discovered that the combination of

• functionalizations are scarce and present new opportunities for further exploration. In consideration of the sustainable nature of C–H activation by photoredox nickel catalysis, further exciting developments are expected in this rapidly evolving research area. Oxidative and reductive quenching cycles of a

Progress and challenges in the synthesis of sequence controlled polysaccharides

• Giulio Fittolani,
• Theodore Tyrikos-Ergas,
• Denisa Vargová,
• Manishkumar A. Chaube and
• Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

• . Additionally, polysaccharides can be converted into useful chemicals upon biodegradation [2][3], contributing to the sustainable development of future materials. Despite polysaccharides’ utility, there are limitations associated with their exploitation. Extraction from natural sources is laborious, low

Asymmetric organocatalyzed synthesis of coumarin derivatives

• Natália M. Moreira,
• Lorena S. R. Martelli and
• Arlene G. Corrêa

Beilstein J. Org. Chem. 2021, 17, 1952–1980, doi:10.3762/bjoc.17.128

• Natalia M. Moreira Lorena S. R. Martelli Arlene G. Correa Centre of Excellence for Research in Sustainable Chemistry, Department of Chemistry, Federal University of São Carlos, 13565-905 São Carlos, SP – Brazil 10.3762/bjoc.17.128 Abstract Coumarin derivatives are essential scaffolds in medicinal

• needed to accomplish procedures that allow recycling and lower catalyst loading, intertwined with the use of green solvents, in order to provide efficient and sustainable synthesis of these important pharmacologically active compounds. Coumarin-derived commercially available drugs. Inhibition of

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

• Renato L. Carvalho,
• Amanda S. de Miranda,
• Mateus P. Nunes,
• Roberto S. Gomes,
• Guilherme A. M. Jardim and
• Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

• Sciences, North Dakota State University, Fargo, ND, United States, Centre for Excellence for Research in Sustainable Chemistry (CERSusChem), Department of Chemistry, Federal University of São Carlos – UFSCar, CEP 13565-905, São Carlos, SP, Brazil 10.3762/bjoc.17.126 Abstract Several valuable biologically

Sustainable manganese catalysis for late-stage C–H functionalization of bioactive structural motifs

• Jongwoo Son

Beilstein J. Org. Chem. 2021, 17, 1733–1751, doi:10.3762/bjoc.17.122

• biologically active small molecules and complex peptides. Keywords: bioactive molecules; 3d transition metals; late-stage functionalization; manganese catalyst; sustainable catalysis; Introduction Manganese, a 3d transition metal, allows for a potentially ideal sustainable catalytic system because of the

• azobenzenes was unveiled [1], manganese catalysts have exhibited a significant capacity for powerful C–H functionalization, and they have therefore been actively utilized in the area of sustainable organic syntheses [2][3][4][5][6]. Catalytic late-stage C–H functionalization, a highly efficient synthetic

• has been devoted to developing sustainable catalytic late-stage C–H functionalization methods that utilize naturally abundant 3d metal catalysts. This review will provide an overview on recent studies on Mn-catalyzed late-stage C–H functionalization of challenging substrates, such as biologically

A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles

• Pezhman Shiri,
• Ali Mohammad Amani and
• Thomas Mayer-Gall

Beilstein J. Org. Chem. 2021, 17, 1600–1628, doi:10.3762/bjoc.17.114

• , high yield, the use of dimethyl carbonate as a sustainable solvent, the use of an efficient alternative source of carbon monoxide, and avoiding a pressurized cylinder are some benefits of this protocol (Scheme 35) [59]. A feasible mechanism is illustrated for the synthesis of 1,2,3-triazole-5

Copper-mediated oxidative C−H/N−H activations with alkynes by removable hydrazides

• Feng Xiong,
• Bo Li,
• Chenrui Yang,
• Liang Zou,
• Wenbo Ma,
• Linghui Gu,
• Ruhuai Mei and
• Lutz Ackermann

Beilstein J. Org. Chem. 2021, 17, 1591–1599, doi:10.3762/bjoc.17.113

• Institute for Sustainable Chemistry (WISCh), Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany 10.3762/bjoc.17.113 Abstract The efficient copper-mediated oxidative C–H alkynylation of benzhydrazides was accomplished with terminal alkynes. Thus, a heteroaromatic removable N-2

• ] auxiliaries (Figure 1a). Besides, the cobalt(II)- [31] or nickel(II)-catalyzed [32][33], pyridine oxide (PyO)-directed tandem alkynylation/annulation was realized by Niu and Song et al., which also provided the 3-methyleneisoindolin-1-one scaffolds (Figure 1b). Notably, a sustainable cupraelectro-catalyzed

• -catalyzed C−H activations with the MHP auxiliary [41][42][43][44]. In continuation of studies on sustainable 3d transition metal-catalyzed C−H activation [41][42][43][44][45][46][47][48][49], we have now discovered a robust copper-promoted oxidative C−H/N−H functionalization with terminal alkynes (Figure 1d

Photoinduced post-modification of graphitic carbon nitride-embedded hydrogels: synthesis of 'hydrophobic hydrogels' and pore substructuring

• Cansu Esen and
• Baris Kumru

Beilstein J. Org. Chem. 2021, 17, 1323–1334, doi:10.3762/bjoc.17.92

• -sustainable semiconductors are slowly being replaced by a new generation of semiconductors. Graphitic carbon nitride (g-CN) is a metal-free polymeric semiconductor that is mainly composed of carbon and nitrogen elements by tri-s-triazine, triazine imide, or heptazine repeating units [16][17][18]. g-CN

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

• Guido Gambacorta,
• James S. Sharley and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

Heterogeneous photocatalytic cyanomethylarylation of alkenes with acetonitrile: synthesis of diverse nitrogenous heterocyclic compounds

• Guanglong Pan,
• Qian Yang,
• Wentao Wang,
• Yurong Tang and
• Yunfei Cai

Beilstein J. Org. Chem. 2021, 17, 1171–1180, doi:10.3762/bjoc.17.89

• reaction mixture and reused several times, illustrating the practicability of this heterogeneous photocatalysis protocol. Further applying this sustainable and environmentally friendly CN-K heterogeneous photocatalyst to realize other synthetic useful transformations is undergoing. Evaluation of catalyst

Nitroalkene reduction in deep eutectic solvents promoted by BH₃NH₃

• Chiara Faverio,
• Monica Fiorenza Boselli,
• Patricia Camarero Gonzalez,
• Alessandra Puglisi and
• Maurizio Benaglia

Beilstein J. Org. Chem. 2021, 17, 1041–1047, doi:10.3762/bjoc.17.83

• safe as well as economically and environmentally sustainable alternative to the traditional organic solvents. Here, we report the combination of an atom-economic, very convenient and inexpensive reagent, such as BH3NH3, with bio-based eutectic mixtures as biorenewable solvents in the synthesis of

• derived from oil but from biorenewable resources, is a topic of primary importance in modern chemistry [1][2]. The solvents are the major contributor to the waste generated in chemical industries, and the elimination or replacement of these with more sustainable alternatives is part of the efforts of the

• whole research community concerned with the concept of a circular economy [3]. In this context, deep eutectic solvents (DESs) have attracted an increasing attention as green, safe, economically and environmentally sustainable alternative to the traditional organic solvents [4]. They are combinations of

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

• Shivani Gulati,
• Stephy Elza John and
• Nagula Shankaraiah

Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71

• environment friendly sustainable technologies and procedures using atom-efficient reactions from suitable starting materials to meet the demands of present as well as future generations [1][2][3]. The need arises as the traditional method of synthesis has become unsustainable both from an environmental and

• majority of the atoms of the starting materials. The ability of forming multiple bonds in one-pot via a multicomponent reaction provides a novel and sustainable method in drug discovery [4]. In the recent years, these reactions have emerged as a promising strategy following green chemistry principles such

• their respective advantage over other synthetic protocols, merging strategy with technology proves to be an asset in organic synthesis. In view of the same, chemists worldwide have experimented with the combination which has proved to be highly efficient and sustainable. Over the past decade

Synthetic reactions driven by electron-donor–acceptor (EDA) complexes

• Zhonglie Yang,
• Yutong Liu,
• Kun Cao,
• Xiaobin Zhang,
• Hezhong Jiang and
• Jiahong Li

Beilstein J. Org. Chem. 2021, 17, 771–799, doi:10.3762/bjoc.17.67

• electron transfer and forming a pair of radical ions trapped in the solvent cage. The pair of radical ions escapes the solvent cage by diffusion to give radical ions, which could initiate chemical reactions or reverse electron transfer (Scheme 1) [6]. The continuously increasing demand for sustainable

Valorisation of plastic waste via metal-catalysed depolymerisation

• Francesca Liguori,
• Carmen Moreno-Marrodán and
• Pierluigi Barbaro

Beilstein J. Org. Chem. 2021, 17, 589–621, doi:10.3762/bjoc.17.53

• selective depolymerisation methods of plastics. Achievements are broken down according to the plastic material, namely polyolefins, polyesters, polycarbonates and polyamides. The focus is on recent advancements targeting sustainable and environmentally friendly processes. Biocatalytic or unselective

• processes, acid–base treatments as well as the production of fuels are not discussed, nor are the methods for the further upgrade of the depolymerisation products. Keywords: catalysis; depolymerisation; plastic; recycling; sustainable; Review 1. Introduction In a circular-economy perspective, wastes are

• kinetics, cost of metals, toxicity, difficulty in catalyst reusing and need of downstream processing. Significant efforts have thus been made to develop greener and sustainable catalytic systems featuring high efficiency under mild conditions. The use of sodium carbonate or bicarbonate as ecofriendly

Designed whole-cell-catalysis-assisted synthesis of 9,11-secosterols

• Marek Kõllo,
• Marje Kasari,
• Villu Kasari,
• Tõnis Pehk,
• Ivar Järving,
• Margus Lopp,
• Arvi Jõers and
• Tõnis Kanger

Beilstein J. Org. Chem. 2021, 17, 581–588, doi:10.3762/bjoc.17.52

• and the increasing importance of methods of sustainable chemistry have brought chemoenzymatic approaches for obtaining natural products, or derivatives thereof, with complex structure into focus [1]. Various enzymatic or semisynthetic methods have also been exploited in the synthesis of steroids [2][3