Modular synthesis of 2-furyl carbinols from 3-benzyldimethylsilylfurfural platforms relying on oxygen-assisted C–Si bond functionalization

• Sebastien Curpanen,
• Per Reichert,
• Gabriele Lupidi,
• Giovanni Poli,
• Julie Oble and
• Alejandro Perez-Luna

Beilstein J. Org. Chem. 2022, 18, 1256–1263, doi:10.3762/bjoc.18.131

• carbinols from renewable feedstock. Keywords: biomass; copper; cyclic siloxanes; 2-furyl carbinols; silicon; Introduction Progress towards the use of nonedible renewable feedstock to replace fossil resources as starting material for high-value chemicals is an important endeavor of modern synthesis [1][2

Inductive heating and flow chemistry – a perfect synergy of emerging enabling technologies

• Conrad Kuhwald,
• Sibel Türkhan and
• Andreas Kirschning

Beilstein J. Org. Chem. 2022, 18, 688–706, doi:10.3762/bjoc.18.70

• ) controller, which regulates the temperature. This feedback loop allowed the temperature of the catalyst bed to be fine-tuned and adjusted in real time to suit the conditions. 2.7 Biofuel production The increasing demand for renewable energy sources goes hand in hand with the sustainable and efficient use of

• is not new, but has become one of the most important topics being discussed today. Due to the energy of hydrogen–hydrogen bonding, water electrolysis enables chemical storage of renewable electricity. Chatenet, Carrey and co-workers showed that the electrocatalytic reaction of hydrogen formation from

Synthesis of 5-unsubstituted dihydropyrimidinone-4-carboxylates from deep eutectic mixtures

• Sangram Gore,
• Sundarababu Baskaran and
• Burkhard König

Beilstein J. Org. Chem. 2022, 18, 331–336, doi:10.3762/bjoc.18.37

• ] based on carbohydrates, urea, and inorganic salts as an alternative to conventional solvents for carrying out a variety of organic transformations [32]. The stable melts are environmentally friendly as they are readily available from bulk renewable resources. Their simple production allows the

Visible-light-mediated copper photocatalysis for organic syntheses

• Yajing Zhang,
• Qian Wang,
• Zongsheng Yan,
• Donglai Ma and
• Yuguang Zheng

Beilstein J. Org. Chem. 2021, 17, 2520–2542, doi:10.3762/bjoc.17.169

• renewable energy and green chemistry for many years. Ruthenium and iridium, which can be used as photoredox catalysts, are expensive and scarce in nature. Thus, the further development of catalysts based on these transition metals is discouraged. Alternative photocatalysts based on copper complexes are

[2 + 1] Cycloaddition reactions of fullerene C₆₀ based on diazo compounds

• Yuliya N. Biglova

Beilstein J. Org. Chem. 2021, 17, 630–670, doi:10.3762/bjoc.17.55

• solar cells [49][50]. In view of the globalization of energy problems, the issues of switching to alternative energy sources are becoming increasingly relevant. Solar energy, like the majority of renewable energy sources, is environmentally friendly and has almost no negative impact on the environment

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

• monobutyltin oxide, using substoichiometric amounts of isosorbide and succinic acid and no solvent at 230 °C reaction temperature. Isosorbide is a safe chemical [246] that is obtainable on the large scale from renewable glucose [247][248]. Because of this and due to the inherent rigid structure, conferring the

• bioderived plastic [252] that is manufactured on a 190 kton scale directly from lactic acid by condensation or from lactide by ring-opening polymerisation (Scheme 8) [253][254]. The main renewable raw material for lactic acid is starch, e.g., from corn, cassava, sugarcane or beet pulp [255]. Owing to the

A sustainable strategy for the straightforward preparation of 2H-azirines and highly functionalized NH-aziridines from vinyl azides using a single solvent flow-batch approach

• Michael Andresini,
• Leonardo Degannaro and
• Renzo Luisi

Beilstein J. Org. Chem. 2021, 17, 203–209, doi:10.3762/bjoc.17.20

• to access aziridines with great structural variability [21]. The reaction of azirines with Grignard and organolithium reagents has been poorly investigated, and only without using green and renewable solvents [22][23]. In turn, 2H-azirines can be smoothly obtained through intramolecular cyclization

Dirhamnolipid ester – formation of reverse wormlike micelles in a binary (primerless) system

• David Liese,
• Hans Henning Wenk,
• Xin Lu,
• Jochen Kleinen and
• Gebhard Haberhauer

Beilstein J. Org. Chem. 2020, 16, 2820–2830, doi:10.3762/bjoc.16.232

• described by Leisinger et al. [9]. Rhamnolipids possess some advantages, that make them interesting candidates as cleaning agents or additives for care applications in the consumer goods industry. They can be produced in a fermentation process from renewable nontropic material [10][11]. RL are also

A proposed sustainability index for synthesis plans based on input provenance and output fate: application to academic and industrial synthesis plans for vanillin as a case study

• John Andraos

Beilstein J. Org. Chem. 2020, 16, 2346–2362, doi:10.3762/bjoc.16.196

• from renewable energy sources (FRE). Valorized input materials originate from renewable, recycled, or reclaimed sources. Valorized output materials are destined for recycling or reclaiming so that they may be used in the same or other chemical processes. Valorized target product refers to that portion

• of the target product that is actually used for its intended purpose. Renewable energy sources are defined as originating from hydroelectric, wind, solar, geothermal, and biomass sources. The computation of SI is illustrated for 22 synthesis plans of the high commodity flavour ingredient vanillin

• fossil-fuel derived and renewable sources. Dutch and Belgian chemical engineers proposed an extended thermodynamic analysis considering exergy and lost work to address the sustainability potential of the chemical process industry [2][3][4]. Horvath and co-workers put forth the following sustainability

Photosensitized direct C–H fluorination and trifluoromethylation in organic synthesis

• Shahboz Yakubov and
• Joshua P. Barham

Beilstein J. Org. Chem. 2020, 16, 2151–2192, doi:10.3762/bjoc.16.183

• , light is inexpensive, nontoxic, noncontaminating, ample (or “limitless” in the case of sunlight) and a renewable source of energy for environmentally-friendly and “green” chemical synthesis. As a consequence of comprehending the detrimental impact of human industry on the environment, new methods to

Three new O-isocrotonyl-3-hydroxybutyric acid congeners produced by a sea anemone-derived marine bacterium of the genus Vibrio

• Dandan Li,
• Enjuro Harunari,
• Tao Zhou,
• Naoya Oku and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1869–1874, doi:10.3762/bjoc.16.154

• nature biodegradable, can be produced from renewable bioresources, and have material properties close to the conventional petroleum-derived plastics, the commercial production and market development are actively pursued by several companies amid the growing plastic waste crisis [14][15]. Vibrio are

Heterogeneous photocatalysis in flow chemical reactors

• Christopher G. Thomson,
• Ai-Lan Lee and
• Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

• emissions and subsequent environmental damage, much of the scientific community has shifted its focus to the development of sustainable methodologies, particularly in synthetic chemistry. The prospect of utilising light as a renewable source of energy to drive chemical reactions is an appealing solution to

Activated carbon as catalyst support: precursors, preparation, modification and characterization

• Melanie Iwanow,
• Tobias Gärtner,
• Volker Sieber and
• Burkhard König

Beilstein J. Org. Chem. 2020, 16, 1188–1202, doi:10.3762/bjoc.16.104

• the production of activated carbon [4]. Fossil and renewable sources for the preparation of activated carbon are discussed in this part of the review, as well as special precursor solutions or ionic liquids and deep eutectic solvents as non-conventional precursor materials. The properties of the

Photophysics and photochemistry of NIR absorbers derived from cyanines: key to new technologies based on chemistry 4.0

• Bernd Strehmel,
• Christian Schmitz,
• Ceren Kütahya,
• Yulian Pang,
• Anke Drewitz and
• Heinz Mustroph

Beilstein J. Org. Chem. 2020, 16, 415–444, doi:10.3762/bjoc.16.40

Oligomeric ricinoleic acid preparation promoted by an efficient and recoverable Brønsted acidic ionic liquid

• Fei You,
• Xing He,
• Song Gao,
• Hong-Ru Li and
• Liang-Nian He

Beilstein J. Org. Chem. 2020, 16, 351–361, doi:10.3762/bjoc.16.34

• . Globally, around one million tons of castor seeds are produced every year and the leading producing areas are India, China, and Brazil [8]. The castor oil has long been used as purgative or laxative to counter constipation and nowadays it is used commercially as a highly renewable resource for the chemical

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