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

• issue to the scientific community. In this context, visible light-induced photoredox catalysis, which is thought to be an abundant, inexpensive, renewable, and nonpolluting chemical transformation, has attracted increasing attention during the past years due to the extraordinary competence and

Why do thioureas and squaramides slow down the Ireland–Claisen rearrangement?

• Dominika Krištofíková,
• Juraj Filo,
• Mária Mečiarová and
• Radovan Šebesta

Beilstein J. Org. Chem. 2019, 15, 2948–2957, doi:10.3762/bjoc.15.290

• other solvents, emphasizing green solvents, which have not been evaluated in Ireland–Claisen rearrangements before. 2-Methyltetrahydrofuran (2-MeTHF) is derived from renewable resources and has a higher boiling point (80 °C) and lower heat of vaporization compared to THF. The Ireland–Claisen

A green, economical synthesis of β-ketonitriles and trifunctionalized building blocks from esters and lactones

• Daniel P. Pienaar,
• Kamogelo R. Butsi,
• Amanda L. Rousseau and
• Dean Brady

Beilstein J. Org. Chem. 2019, 15, 2930–2935, doi:10.3762/bjoc.15.287

• cyclohexyl 15 (68%) analogues. We were pleased to obtain the highly versatile and synthetically useful cinnamoylacetonitrile 17 [20] from renewable ethyl cinnamate in 64% yield, as this yield was comparable to more expensive and hazardous lithiation protocols [7]. Finally, we attempted method optimization

Palladium-catalyzed Sonogashira coupling reactions in γ-valerolactone-based ionic liquids

• László Orha,
• József M. Tukacs,
• László Kollár and
• László T. Mika

Beilstein J. Org. Chem. 2019, 15, 2907–2913, doi:10.3762/bjoc.15.284

• Ullmann-type N–C coupling reactions could be performed in tetrabutylphosphonium 4-alkoxyvalerate-type ionic liquids, which can easily be synthesized from the renewable platform chemical γ-valerolactone and have negligible vapor pressures even at high temperatures [34]. In order to extend the applicability

Ugi reaction-derived prolyl peptide catalysts grafted on the renewable polymer polyfurfuryl alcohol for applications in heterogeneous enamine catalysis

• Alexander F. de la Torre,
• Gabriel S. Scatena,
• Oscar Valdés,
• Daniel G. Rivera and
• Márcio W. Paixão

Beilstein J. Org. Chem. 2019, 15, 1210–1216, doi:10.3762/bjoc.15.118

• high reaction yields and reduction of waste – aspects recognized as compatible with the principles of green chemistry [1][2][3][4][5].. However, almost all polymers used in the development of supported organocatalysts are made from non-renewable sources and composed of non-biodegradable materials (e.g

• ., polystyrene) [1][2][3]. When aiming at implementing large-scale catalytic processes with supported organocatalysts, a relevant “green” premise is the use of renewable and readily available solid supports [1][2][3][4][5]. Accordingly, we envisioned the utilization of the polymer polyfurfuryl alcohol (PFA

• ) – derived from a renewable resource like sugar cane biomass – for the incorporation of chiral pyrrolidine-based motifs capable to catalyze relevant asymmetric reactions. The incorporation of an organocatalyst into a polymer support requires either conjugation to the polymer or functionalization with a

Synthesis of a novel category of pseudo-peptides using an Ugi three-component reaction of levulinic acid as bifunctional substrate, amines, and amino acid-based isocyanides

• Maryam Khalesi,
• Azim Ziyaei Halimehjani and
• Jürgen Martens

Beilstein J. Org. Chem. 2019, 15, 852–857, doi:10.3762/bjoc.15.82

• by acid catalysis from renewable resources, such as sugars, lignocellulosic biomass and waste materials [18]. It can be used as a bifunctional precursor for the synthesis of pharmaceuticals, plasticizers, and different additives [19]. Furthermore, it is recognized as an excellent starting material

Systematic synthetic study of four diastereomerically distinct limonene-1,2-diols and their corresponding cyclic carbonates

• Hiroshi Morikawa,
• Jun-ichi Yamaguchi,
• Shun-ichi Sugimura,
• Masato Minamoto,
• Yuuta Gorou,
• Hisatoyo Morinaga and
• Suguru Motokucho

Beilstein J. Org. Chem. 2019, 15, 130–136, doi:10.3762/bjoc.15.13

• their characteristic signals. Keywords: cyclic carbonate; diastereomer; diol; limonene; NMR; Introduction (R)-Limonene (LM) is a naturally occurring terpene, and therefore a very attractive and renewable resource [1]. Its derivatives have versatilely and widely been studied [1][2][3][4]. Otherwise

Organometallic vs organic photoredox catalysts for photocuring reactions in the visible region

• Aude-Héloise Bonardi,
• Frédéric Dumur,
• Guillaume Noirbent,
• Jacques Lalevée and
• Didier Gigmes

Beilstein J. Org. Chem. 2018, 14, 3025–3046, doi:10.3762/bjoc.14.282

• absorbing compound and suitable additives under light to induce a catalytical cycle. As light is an inexhaustible and renewable energy, photochemistry has dealt a great interest into organic chemistry and green chemistry since the early 20th century [15]. By absorbing light, the compound reaches an

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

• isolation of products, very short reaction times (only 10 s), and better yields. The use of glycerol as a starting material is another important advantage because it is the main byproduct in the biodiesel industry and the application of renewable feedstocks for the preparation of suitable chemicals and

Synthesis of a tyrosinase inhibitor by consecutive ethenolysis and cross-metathesis of crude cashew nutshell liquid

• Jacqueline Pollini,
• Valentina Bragoni and
• Lukas J. Gooßen

Beilstein J. Org. Chem. 2018, 14, 2737–2744, doi:10.3762/bjoc.14.252

• subsequent hydrogenation step. Overall, the target compound was obtained in an overall yield of 61% based on the unsaturated anacardic acid content and 34% based on the crude CNSL. Keywords: cashew nutshell liquid; cross-metathesis; renewable feedstock; sustainable chemistry; tyrosinase inhibitor

• ; Introduction Cashew nutshell liquid (Scheme 1) is an ideal renewable feedstock. This non-edible industrial waste product, derived from the cashew nut processing, is abundant available and cheap [1][2][3]. The annual production of cashew nuts with shell reached 4.9 million tons in 2016 [4], leading to an

• neurodegenerative diseases [30]. Therefore, the study and development of tyrosinase inhibitors from renewable resources is of particular interest for research and industry [31][32]. Fu et al. investigated naturally occurring ginkgolic acids which they selectively synthesized from 2,6-dihydroxybenzoic acid (4), and

Cobalt- and rhodium-catalyzed carboxylation using carbon dioxide as the C1 source

• Tetsuaki Fujihara and
• Yasushi Tsuji

Beilstein J. Org. Chem. 2018, 14, 2435–2460, doi:10.3762/bjoc.14.221

• Tetsuaki Fujihara Yasushi Tsuji Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan 10.3762/bjoc.14.221 Abstract Carbon dioxide (CO2) is one of the most important materials as renewable chemical feedstock. In this

• [2 + 2 + 2] cycloaddition of diynes and CO2 proceeds to afford pyrones. Keywords: carbon dioxide; carboxylation; cobalt; homogeneous catalysts; rhodium; Introduction Carbon dioxide (CO2) is one of the most important materials as renewable feedstock [1][2][3][4]. However, the thermodynamic and

Microfluidic light-driven synthesis of tetracyclic molecular architectures

• Javier Mateos,
• Nicholas Meneghini,
• Marcella Bonchio,
• Nadia Marino,
• Tommaso Carofiglio,
• Xavier Companyó and
• Luca Dell’Amico

Beilstein J. Org. Chem. 2018, 14, 2418–2424, doi:10.3762/bjoc.14.219

• molecules. Keywords: [4 + 2] photoenol; cycloaddition; flow chemistry; microfluidic photoreactor; photoredox catalysis; synthetic photochemistry; Introduction In recent years synthetic photochemistry has become highly sophisticated [1]. The opportunity of using renewable energy sources to transform and

Heterogeneous acidic catalysts for the tetrahydropyranylation of alcohols and phenols in green ethereal solvents

• Ugo Azzena,
• Massimo Carraro,
• Gloria Modugno,
• Luisa Pisano and
• Luigi Urtis

Beilstein J. Org. Chem. 2018, 14, 1655–1659, doi:10.3762/bjoc.14.141

• , hydrophobicity, easy drying and recovery possibilities. Additionally, CPME is produced via a 100% atom economical reaction [19][20], whilst 2-MeTHF is accessible from renewable resources [21][23]. Finally, it is worth noting that besides being moderately irritant, both solvents are characterized by low

Cobalt–metalloid alloys for electrochemical oxidation of 5-hydroxymethylfurfural as an alternative anode reaction in lieu of oxygen evolution during water splitting

• Jonas Weidner,
• Stefan Barwe,
• Kirill Sliozberg,
• Stefan Piontek,
• Justus Masa,
• Ulf-Peter Apfel and
• Wolfgang Schuhmann

Beilstein J. Org. Chem. 2018, 14, 1436–1445, doi:10.3762/bjoc.14.121

• reaction; Introduction Energy production from renewable sources continues to contribute to a significant growing share of current and future energy requirements. However, the intermittency of renewable energy sources renders it a necessity to develop new technologies to convert and store surplus energy

• , which can be made accessible on demand [1]. Energy storage in hydrogen as a highly versatile energy carrier, which can be inexhaustibly obtained from water, is very appealing [2]. For the conversion of renewable energy into storable hydrogen, electrochemical water splitting turns out to be among the

Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols

• Xinyun Liu,
• Johnny H. Phan,
• Benjamin J. Haugeberg,
• Shrikant S. Londhe and
• Michael D. Clift

Beilstein J. Org. Chem. 2017, 13, 2895–2901, doi:10.3762/bjoc.13.282

• common [29][30][31][32] despite the fact that these methods employ renewable resources, such as amino acids and their derivatives, as starting materials. In fact, only a few reports describing the oxidative deformylation of amino alcohols have been published [33][34][35], and in all of these reports

Mechanochemical synthesis of small organic molecules

• Tapas Kumar Achar,
• Anima Bose and
• Prasenjit Mal

Beilstein J. Org. Chem. 2017, 13, 1907–1931, doi:10.3762/bjoc.13.186

• Tapas Kumar Achar Anima Bose Prasenjit Mal School of Chemical Sciences, National Institute of Science Education and Research (NISER) Bhubaneswar, HBNI, P.O. Bhimpur-Padanpur, Via Jatni, Khurda 752050, Odisha, India 10.3762/bjoc.13.186 Abstract With the growing interest in renewable energy and

Enzymatic synthesis of glycosides: from natural O- and N-glycosides to rare C- and S-glycosides

• Jihen Ati,
• Pierre Lafite and
• Richard Daniellou

Beilstein J. Org. Chem. 2017, 13, 1857–1865, doi:10.3762/bjoc.13.180

• published roadmap for glycosciences in Europe, carbohydrates are expected, both by academics and industrials, to become key players in a near future in tremendous fields such as pharmaceuticals and personalized biomedicine, food, materials and renewable resources, and bioenergy for examples [2]. To achieve

Pd(OAc)₂/Ph₃P-catalyzed dimerization of isoprene and synthesis of monoterpenic heterocycles

• Dominik Kellner,
• Maximilian Weger,
• Andrea Gini and
• Olga García Mancheño

Beilstein J. Org. Chem. 2017, 13, 1807–1815, doi:10.3762/bjoc.13.175

• Dominik Kellner Maximilian Weger Andrea Gini Olga Garcia Mancheno Institute of Organic Chemistry, University of Regensburg, Universitätsstr. 31, 93040 Regensburg, Germany Straubing Center of Science for Renewable Resources, 94315 Straubing, Germany 10.3762/bjoc.13.175 Abstract The palladium

• from renewable sources such as sugars has been considered as a competitive sustainable synthetic alternative [21][22]. Although the dimerization of isoprene is significantly more difficult compared to the dimerization of 1,3-butadiene, it would lead to synthetically useful linear monoterpenic

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

• efficient one-pot cascade aldol/cyclization methodology using the low-cost and renewable feedstock glycerol as the solvent. A broad substrate scope for β-keto acids is strongly compatible with this catalytic process, affording a wide variety of 3-substituted phthalides in good to excellent yields. Further

Sugar-based micro/mesoporous hypercross-linked polymers with in situ embedded silver nanoparticles for catalytic reduction

• Qing Yin,
• Qi Chen,
• Li-Can Lu and
• Bao-Hang Han

Beilstein J. Org. Chem. 2017, 13, 1212–1221, doi:10.3762/bjoc.13.120

• ][14][15]. However, most aromatic skeleton monomers are non-renewable and could generate additional environmental problems. Therefore, the selection and use of low cost, green, raw materials is critical. Sugars are a ubiquitous resource, which plays many different and important roles in the world [16

Molecular-level architectural design using benzothiadiazole-based polymers for photovoltaic applications

• Vinila N. Viswanathan,
• Arun D. Rao,
• Upendra K. Pandey,
• Arul Varman Kesavan and
• Praveen C. Ramamurthy

Beilstein J. Org. Chem. 2017, 13, 863–873, doi:10.3762/bjoc.13.87

• . Department of Energy (Office of Science, Office of Basic Energy Sciences, and Energy Efficiency and Renewable Energy, Solar Energy Technology Program, under subcontract DE-AC36-08GO28308 to the National Renewable Energy Laboratory, Golden, Colorado) and the Government of India, through the Department of

Cyclodextrins tethered with oligolactides – green synthesis and structural assessment

• Cristian Peptu,
• Mihaela Balan-Porcarasu,
• Alena Šišková,
• Ľudovít Škultéty and
• Jaroslav Mosnáček

Beilstein J. Org. Chem. 2017, 13, 779–792, doi:10.3762/bjoc.13.77

• ) of cyclic esters [6], oxiranes [7] and oxazolines [8]. However, the ROP of cyclic esters should also be considered as a method of producing polymer-modified CDs with some particular features, such as possibility of employing green polymerization procedures and availability of renewable monomers like

Energy down converting organic fluorophore functionalized mesoporous silica hybrids for monolith-coated light emitting diodes

• Markus Börgardts and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2017, 13, 768–778, doi:10.3762/bjoc.13.76

• alternative, eventually starting from renewable organic materials [8][9]. Other than inorganic luminophores these organic analogues cannot simply be intercalated in a robust inorganic host structure and, therefore, ligating materials are required. Since the host structure should not undergo photodegradation

Fluorescent carbon dots from mono- and polysaccharides: synthesis, properties and applications

• Stephen Hill and
• M. Carmen Galan

Beilstein J. Org. Chem. 2017, 13, 675–693, doi:10.3762/bjoc.13.67

• Glucose-based fluorescent carbon dots Sustainable syntheses of CDs have driven researchers to find readily available, cheap and renewable carbon sources of which the monosaccharide glucose is an ideal candidate. Not only is glucose cheap and commercially available, but also has a low carbonisation

Revaluation of biomass-derived furfuryl alcohol derivatives for the synthesis of carbocyclic nucleoside phosphonate analogues

• Bemba Sidi Mohamed,
• Christian Périgaud and
• Christophe Mathé

Beilstein J. Org. Chem. 2017, 13, 251–256, doi:10.3762/bjoc.13.28

• compounds were evaluated for their activity against a large number of viruses. However, none of them showed significant antiviral activity or cytotoxicity. Keywords: analogue; antiviral; carbocyclic; nucleoside; phosphonate; Introduction Biomass is a valuable resource in search of renewable organic carbon