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

Diels–Alder reactions of myrcene using intensified continuous-flow reactors

• Christian H. Hornung,
• Miguel Á. Álvarez-Diéguez,
• Thomas M. Kohl and
• John Tsanaktsidis

Beilstein J. Org. Chem. 2017, 13, 120–126, doi:10.3762/bjoc.13.15

• continuous-flow approach provides a facile alternative scale-up route to conventional batch processing, and it helps to intensify the synthesis protocol by applying higher reaction temperatures and shorter reaction times. Keywords: continuous processing; flow chemistry; renewable feedstock; surfactant

• ; Introduction Over the past years, great attention has been devoted to finding alternative, renewable feedstocks to fossil oil for the production of fuel and industrial chemicals. Especially, high value added products from fine chemicals, specialty chemicals or the pharmaceuticals sector allow for a ‘drop-in

• ’ replacement of existing, fossil resources based synthesis routes with economic alternatives based on renewable sources. Besides chemical platforms based on sugar, lignin or fatty acid containing feedstocks, terpenes present another plant derived feedstock which is of great interest for a variety of industrial

High performance p-type molecular electron donors for OPV applications via alkylthiophene catenation chromophore extension

• Paul B. Geraghty,
• Calvin Lee,
• Jegadesan Subbiah,
• Wallace W. H. Wong,
• James L. Banal,
• Mohammed A. Jameel,
• Trevor A. Smith and
• David J. Jones

Beilstein J. Org. Chem. 2016, 12, 2298–2314, doi:10.3762/bjoc.12.223

• solar cells. Supporting Information Supporting Information File 390: Synthetic procedures, NMR spectra, MALDI, TGA, DSC, CVs, POM methods and images, UV–vis, fluorescence, and DFT cartesian coordinates. Acknowledgements This work was made possible by support from the Australian Renewable Energy Agency

Isosorbide and dimethyl carbonate: a green match

• Fabio Aricò and
• Pietro Tundo

Beilstein J. Org. Chem. 2016, 12, 2256–2266, doi:10.3762/bjoc.12.218

• has gained exceptional attention in the scientific community. This interest has been prompted by the substitution of petroleum-based compounds with renewable substances with the aim of establishing a bio-based economically self-sustained industry [1]. In this prospect the US Department of Energy (DOE

• should be pointed out that, despite D-sorbitol and isosorbide are renewable materials, their derivatizations do not always follow the green chemistry principles. In this prospect, the present work is focussed on the reactivity of D-sorbitol and isosorbide with the green reagent and solvent dimethyl

• other noxious methylating agents in methylation reactions [24][25][26][27][28][29][30][31][32][33][34][35]. The reactions between the bio-based chemicals D-sorbitol or isosorbide and DMC, are very appealing as they encompass the preparation, as well as the transformation of a renewable resource into

Diels–Alder reactions in confined spaces: the influence of catalyst structure and the nature of active sites for the retro-Diels–Alder reaction

• Ángel Cantín,
• M. Victoria Gomez and
• Antonio de la Hoz

Beilstein J. Org. Chem. 2016, 12, 2181–2188, doi:10.3762/bjoc.12.208

• converted into a variety of liquid hydrocarbon fuels and fuel additives [11][12]. Catalysis is considered as one of the foundational pillars of green chemistry. Catalysis often reduces the energy requirements, permits the use of renewable feedstocks and less toxic reagents. Moreover, in most cases yields

Silica-supported sulfonic acids as recyclable catalyst for esterification of levulinic acid with stoichiometric amounts of alcohols

• Raimondo Maggi,
• N. Raveendran Shiju,
• Veronica Santacroce,
• Giovanni Maestri,
• Franca Bigi and
• Gadi Rothenberg

Beilstein J. Org. Chem. 2016, 12, 2173–2180, doi:10.3762/bjoc.12.207

• : esterification; heterogeneous catalysis; renewable feedstocks; supported organic catalysts; sustainable chemistry; Introduction Vegetal biomass is mankind’s only source of renewable carbon on a human timescale. It is abundantly available, with the potential of replacing fossil-based carbon on a scale sufficient

Superelectrophilic activation of 5-hydroxymethylfurfural and 2,5-diformylfuran: organic synthesis based on biomass-derived products

• Dmitry S. Ryabukhin,
• Dmitry N. Zakusilo,
• Mikhail O. Kompanets,
• Anton A.Tarakanov,
• Irina A. Boyarskaya,
• Tatiana O. Artamonova,
• Mikhail A. Khohodorkovskiy,
• Iosyp O. Opeida and
• Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2016, 12, 2125–2135, doi:10.3762/bjoc.12.202

• ; Introduction Nowadays great attention is paid to the use of renewable resources for obtaining fine chemicals and fuels (see numerous reviews [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16]). The biorefinery of renewable lignin-carbohydrate materials affords various low-molecular weight organic

Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulation

• Kirsty L. Wilson,
• Alan R. Kennedy,
• Jane Murray,
• Ben Greatrex,
• Craig Jamieson and
• Allan J. B. Watson

Beilstein J. Org. Chem. 2016, 12, 2005–2011, doi:10.3762/bjoc.12.187

• solvents; however, despite their utility, these solvents are incompatible with the drive towards more sustainable chemical synthesis. Herein, we describe the scope and limitations of an alternative to DMF derived from renewable sources (CyreneTM) in Sonogashira cross-coupling and Cacchi-type annulations

Effect of the π-conjugation length on the properties and photovoltaic performance of A–π–D–π–A type oligothiophenes with a 4,8-bis(thienyl)benzo[1,2-b:4,5-b′]dithiophene core

• Ni Yin,
• Lilei Wang,
• Yi Lin,
• Jinduo Yi,
• Lingpeng Yan,
• Junyan Dou,
• Hai-Bo Yang,
• Xin Zhao and
• Chang-Qi Ma

Beilstein J. Org. Chem. 2016, 12, 1788–1797, doi:10.3762/bjoc.12.169

• ; benzodithiophene; π-bridge; chain length effect; organic solar cell; Introduction Solution-processed organic solar cells (OSCs) are considered to be one of the most promising renewable energy technologies because of the advantages of low cost, lightweight, flexibility, and great potentials in large-scale

Experimental and theoretical insights in the alkene–arene intramolecular π-stacking interaction

• Valeria Corne,
• Ariel M. Sarotti,
• Carmen Ramirez de Arellano,
• Rolando A. Spanevello and
• Alejandra G. Suárez

Beilstein J. Org. Chem. 2016, 12, 1616–1623, doi:10.3762/bjoc.12.158

•  1). Saponification of adducts 11 and 12 provided the free 5-norbornenecarboxylic acid and the chiral auxiliaries 5a and 5b in excellent yields, which can be reused. Conclusion We have reported the synthesis of chiral acrylates derived from renewable feedstock as models to study arene–alkene π

Catalytic Chan–Lam coupling using a ‘tube-in-tube’ reactor to deliver molecular oxygen as an oxidant

• Carl J. Mallia,
• Paul M. Burton,
• Alexander M. R. Smith,
• Gary C. Walter and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2016, 12, 1598–1607, doi:10.3762/bjoc.12.156

• potentially an improvement on the use of stiochiometric copper(II) acetate in continuous flow, the use of TEMPO or tert-butyl peroxybenzoate as a co-oxidant introduces waste. Employing oxygen gas as an oxidant is preferred as it is cheap, renewable and environmentally benign. We therefore set out to develop a

Star-shaped and linear π-conjugated oligomers consisting of a tetrathienoanthracene core and multiple diketopyrrolopyrrole arms for organic solar cells

• Hideaki Komiyama,
• Chihaya Adachi and
• Takuma Yasuda

Beilstein J. Org. Chem. 2016, 12, 1459–1466, doi:10.3762/bjoc.12.142

• , including organic solar cells (OSCs) [1][2][3][4]. OSCs have drawn much attention as promising next-generation renewable energy sources because abundant sun-light energy can be directly converted into electricity. Recently, the power conversion efficiencies (PCEs) of OSCs based on small molecules with bulk

Separation and identification of indene–C₇₀ bisadduct isomers

• Bolong Zhang,
• Jegadesan Subbiah,
• David J. Jones and
• Wallace W. H. Wong

Beilstein J. Org. Chem. 2016, 12, 903–911, doi:10.3762/bjoc.12.88

• separation; electron acceptor; fullerene bisadduct; organic solar cell; regioisomers; Introduction Organic solar cells (OSCs) are an emerging renewable energy technology that has achieved remarkable progress over the past two decades. Compared to traditional inorganic semiconductor solar cells, OSCs promise

• well as device fabrication and testing. Acknowledgements This work was made possible by support from the Australian Renewable Energy Agency which funds the project grants within the Australian Centre for Advanced Photovoltaics. WWHW is supported by an Australian Research Council Future Fellowship

Biocatalysis for the application of CO₂ as a chemical feedstock

• Apostolos Alissandratos and
• Christopher J. Easton

Beilstein J. Org. Chem. 2015, 11, 2370–2387, doi:10.3762/bjoc.11.259

• current oxidative technologies that rely on diminishing natural fossil-fuel deposits. Enzymes that catalyse CO2 fixation steps in carbon assimilation pathways are promising catalysts for the sustainable transformation of this safe and renewable feedstock into central metabolites. These may be further

• as a renewable chemical feedstock, greatly enabling a sustainable carbon bio-economy. Keywords: biocatalysis; carboxylase; CO2 transformation; formate dehydrogenase; RuBisCO; Introduction Depletion of fossil-fuel feedstocks and pollution resulting from their unsustainable processing and use

• constitute challenging global issues [1][2]. Catalysis has an important role to play in addressing these challenges through the generation of fuels and commodity chemicals from renewable sources in a sustainable manner [3]. In this context, CO2 has become a compound of key interest as it is one of the main

Cross metathesis of unsaturated epoxides for the synthesis of polyfunctional building blocks

• Meriem K. Abderrezak,
• Kristýna Šichová,
• Nancy Dominguez-Boblett,
• Antoine Dupé,
• Zahia Kabouche,
• Christian Bruneau and
• Cédric Fischmeister

Beilstein J. Org. Chem. 2015, 11, 1876–1880, doi:10.3762/bjoc.11.201

• enabled the achievement of more challenging transformations such as cross metathesis reactions [6], stereoselective transformations [7] including the selective synthesis of Z-olefins [8][9][10][11]. Recently, the cross metathesis of renewable compounds with electron-deficient olefins was developed as a

Robust bifunctional aluminium–salen catalysts for the preparation of cyclic carbonates from carbon dioxide and epoxides

• Yuri A. Rulev,
• Zalina Gugkaeva,
• Victor I. Maleev,
• Michael North and
• Yuri N. Belokon

Beilstein J. Org. Chem. 2015, 11, 1614–1623, doi:10.3762/bjoc.11.176

• mixture and reused. Keywords: aluminium; carbon dioxide; cyclic carbonate; epoxide; salen; Introduction Carbon dioxide is a renewable and inexpensive carbon source, so great efforts have been directed at developing novel methods for the valorization of this abundant raw material [1]. One way of

CO₂ Chemistry

• Thomas E. Müller and
• Walter Leitner

Beilstein J. Org. Chem. 2015, 11, 675–677, doi:10.3762/bjoc.11.76

• ; reactivity; renewable resources; sustainability; value generation; It is our pleasure to introduce this Thematic Series on CO2 chemistry for the Beilstein Journal of Organic Chemistry (BJOC). Today’s growing demand for energy, materials and chemicals has prompted renewed interest in CO2 chemistry. More

• resource-efficient chemical processes are being implemented, while we are facing the change from a fossil fuel-based society to one that must rely on the sustainable use of renewable resources. Although there are many ways to harness renewable energy resources, much of the needed materials and chemicals

• will continue to be carbon-based. One of the most abundant renewable resources of carbon is carbon dioxide (Figure 1). Carbon capture technologies are being implemented [1] to capture a part of the yearly anthropogenic CO2 emission of 36,600 million metric tons of CO2 [2]. If only a fraction of the

Hydrogenation of unactivated enamines to tertiary amines: rhodium complexes of fluorinated phosphines give marked improvements in catalytic activity

• Sergey Tin,
• Tamara Fanjul and
• Matthew L. Clarke

Beilstein J. Org. Chem. 2015, 11, 622–627, doi:10.3762/bjoc.11.70

• tetrasubstituted enamines. The use of the sustainable and environmentally benign solvent (R)-limonene for the reaction is also reported with the amine isolated by acid extraction. Keywords: alkenes; homogeneous catalysis; hydrogenation; renewable solvents; tertiary amines; Introduction A potentially very direct

• tetrasubstituted enamines has not been carried out before. The use of green, non-toxic and renewable solvent (R)-limonene is introduced here as a potentially promising solvent for amine synthesis. This solvent could prove a particularly useful green solvent for any reaction that involved an aqueous/organic work-up