Synthesis of alkynyl-substituted camphor derivatives and their use in the preparation of paclitaxel-related compounds

• M. Fernanda N. N. Carvalho,
• Rudolf Herrmann and
• Gabriele Wagner

Beilstein J. Org. Chem. 2017, 13, 1230–1238, doi:10.3762/bjoc.13.122

• all atoms of the starting material are found in the product, and thus fulfil an important requirement of “green chemistry” [31]. However, a different Pt(II)-catalysed reaction cascade was observed for 4c, with adamantyl groups at the alkynes. Here, the annulation step is followed by a C–H bond

Strategies in megasynthase engineering – fatty acid synthases (FAS) as model proteins

• Manuel Fischer and
• Martin Grininger

Beilstein J. Org. Chem. 2017, 13, 1204–1211, doi:10.3762/bjoc.13.119

• biologists for more than two decades to create engineered pipelines for the directed synthesis of bioactive compounds [41][42]. Engineering of megasynthases provides the opportunity to complement or replace synthetic chemical strategies for natural compound production with sustainable, green-chemistry

New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized

• Maryna V. Murlykina,
• Maryna N. Kornet,
• Sergey M. Desenko,
• Svetlana V. Shishkina,
• Oleg V. Shishkin,
• Aleksander A. Brazhko,
• Vladimir I. Musatov,
• Erik V. Van der Eycken and
• Valentin A. Chebanov

Beilstein J. Org. Chem. 2017, 13, 1050–1063, doi:10.3762/bjoc.13.104

• 48 h gave compound 4o (Table 3). It should be noted that the conditions of method B are also suitable for obtaining imidazopyrazoles 4a–m in comparatively high yields; however, the synthesis in EtOH/H2O medium is preferred from the point of view of green chemistry. Thereby, the optimal methodology

Effect of the ortho-hydroxy group of salicylaldehyde in the A³ coupling reaction: A metal-catalyst-free synthesis of propargylamine

• Sujit Ghosh,
• Kinkar Biswas,
• Suchandra Bhattacharya,
• Pranab Ghosh and
• Basudeb Basu

Beilstein J. Org. Chem. 2017, 13, 552–557, doi:10.3762/bjoc.13.53

• acetylene, established as a general protocol, and is believed to be of interest for synthetic chemists from green chemistry. Keywords: A3 coupling; metal-catalyst-free; propargylamine; salicylaldehyde; terminal alkyne; Introduction Propargylamines are important synthetic intermediates for the preparation

Contribution of microreactor technology and flow chemistry to the development of green and sustainable synthesis

• Flavio Fanelli,
• Giovanna Parisi,
• Leonardo Degennaro and
• Renzo Luisi

Beilstein J. Org. Chem. 2017, 13, 520–542, doi:10.3762/bjoc.13.51

• chemistry could play in the near future for a sustainable development. Keywords: flash chemistry; flow chemistry; green chemistry; microreactor technology; sustainable synthesis; Introduction Green chemistry’s birth was driven by the necessity to consider and face the urgent question of sustainability

• becoming a new technique for fulfilling several of the twelve green chemistry principles. The microreactor approach, could provide protection, preserves atom economy, guarantees less hazardous chemical synthesis and allows the use of safer solvents and auxiliaries. Furthermore, it pushes towards designing

• organic synthesis, very recent examples have been selected and will be discussed here. In the context of green chemistry [11], protecting-group free organic synthesis has received particular attention in the last years, because of atom economy [12][13][14][15] and reduction of synthetic steps [16]. It has

Synthesis of 1-indanones with a broad range of biological activity

• Marika Turek,
• Dorota Szczęsna,
• Marek Koprowski and
• Piotr Bałczewski

Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48

• -arylpropanoic and 4-arylbutanoic acids has been reported in 2015 by Le et al. [22]. The authors applied a microwave-assisted intramolecular Friedel–Crafts acylation catalyzed by metal triflate in triflate-anion containing ionic liquids. This synthesis proceeded with the goals of green chemistry and allowed to

NMR reaction monitoring in flow synthesis

• M. Victoria Gomez and
• Antonio de la Hoz

Beilstein J. Org. Chem. 2017, 13, 285–300, doi:10.3762/bjoc.13.31

• analysis of a reaction is one of the key principles of green chemistry [51] for pollution prevention. However, on-line and in-line analysis together with the use of flow chemistry and the appropriate software for analysis, determination of the kinetic and thermodynamic parameters and for process

Green chemistry

• Luigi Vaccaro

Beilstein J. Org. Chem. 2016, 12, 2763–2765, doi:10.3762/bjoc.12.273

• Luigi Vaccaro Laboratory of Green Synthetic Organic Chemistry, Dipartimento di Chimica, Biologia e Biotecnologie, Università di Perugia, Via Elce di Sotto, 8 06123 Perugia, Italia 10.3762/bjoc.12.273 Keywords: green chemistry; sustainable chemistry; Since their initial appearance in the

• scientific literature, the terms "green" and "sustainable" have been increasingly used and are nowadays ubiquitously present in the terminology of several research areas. The seminal origin of what is considered “green chemistry” today might be ascribed to the launch of the Responsible Care® initiative by

• the American Chemistry Council (ACC) [1] and to the Brundtland report [2]. The concept was then further refined and completed with the Pollution Prevention Act (approved by the American Congress [3]) and the definition of the Anastas and Warner’s 12 principles of green chemistry [4][5]. Very generally

Interactions between cyclodextrins and cellular components: Towards greener medical applications?

• Loïc Leclercq

Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261

Copper-catalyzed asymmetric sp³ C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst

• Pierre Querard,
• Inna Perepichka,
• Eli Zysman-Colman and
• Chao-Jun Li

Beilstein J. Org. Chem. 2016, 12, 2636–2643, doi:10.3762/bjoc.12.260

• Pierre Querard Inna Perepichka Eli Zysman-Colman Chao-Jun Li Department of Chemistry, FQRNT Center for Green Chemistry and Catalysis, McGill University, 801 Sherbrooke Street West, Montreal, Quebec H3A 0B8, Canada Organic Semiconductor Centre, EaStCHEM School of Chemistry, University of St Andrews

Selective synthesis of thioethers in the presence of a transition-metal-free solid Lewis acid

• Federica Santoro,
• Matteo Mariani,
• Federica Zaccheria,
• Rinaldo Psaro and
• Nicoletta Ravasio

Beilstein J. Org. Chem. 2016, 12, 2627–2635, doi:10.3762/bjoc.12.259

• the green chemistry point of view would be the direct substitution of alcohols (that are also available at low cost) with thiols. In this case the only byproduct will be water. However, due to the lack of a good leaving group the use of an acid catalyst is mandatory. Both Brønsted and Lewis acids can

• protocol here described is very advantageous from the point of view of Green Chemistry. The direct substitution of hydroxy groups in alcohols is very difficult and generally they have to be converted into better leaving groups, typically halides, before reaction with nucleophiles. This process generates

Catalytic Wittig and aza-Wittig reactions

• Zhiqi Lao and
• Patrick H. Toy

Beilstein J. Org. Chem. 2016, 12, 2577–2587, doi:10.3762/bjoc.12.253

• completed. However, will the research results summarized herein remain merely intellectual achievements or will they become commonly used synthetic methods in the future? Perhaps the answer to this question is how these new reaction systems are viewed from an environmental/green chemistry perspective. In

A new paradigm for designing ring construction strategies for green organic synthesis: implications for the discovery of multicomponent reactions to build molecules containing a single ring

• John Andraos

Beilstein J. Org. Chem. 2016, 12, 2420–2442, doi:10.3762/bjoc.12.236

• adopting principles of green chemistry. Such principles combine the goals of optimizing reactions to desired products and inventing novel reactions [1][2][3][4][5][6]. Central to these objectives is the design of highly atom-economical reactions [7][8] that maximize the transfer of atoms found in reactant

Efficient mechanochemical synthesis of regioselective persubstituted cyclodextrins

• Laszlo Jicsinszky,
• Marina Caporaso,
• Katia Martina,
• Emanuela Calcio Gaudino and
• Giancarlo Cravotto

Beilstein J. Org. Chem. 2016, 12, 2364–2371, doi:10.3762/bjoc.12.230

• millimolar scale, they are easily scalable. Keywords: green chemistry; nucleophilic substitution; planetary ball mill; siRNA delivery intermediate; sugammadex; Introduction Cyclodextrins (CDs) are cyclic α(1→4)glucopyranosides and have been fully described in a number of publications [1][2][3]. They are

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

• reactivity of isosorbide and the non-toxic properties of DMC represent indeed a green match leading to several industrial appealing potential applications. Keywords: carbohydrate chemistry; D-sorbitol; dimethyl carbonate; green chemistry; isosorbide; Review Introduction In the last twenty years biorefinery

• 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

• relevant products that might substitute fossil-based compounds and that are a poignant example of innovation at molecular level that nicely combines green chemistry reactions with biorefinery of carbohydrates. The DOE “Top 10” report [2]. Chemical structure of isosorbide and its epimers isomannide and

Tunable microwave-assisted method for the solvent-free and catalyst-free peracetylation of natural products

• Manuela Oliverio,
• Paola Costanzo,
• Monica Nardi,
• Carla Calandruccio,
• Raffaele Salerno and
• Antonio Procopio

Beilstein J. Org. Chem. 2016, 12, 2222–2233, doi:10.3762/bjoc.12.214

• Figure 1 (Synthos 3000, equipped with 64-MG5 rotor). Solvent free and catalyst free peracetylation MW assisted of alcohols and polyols. Process green chemistry metrics. Supporting Information Supporting Information File 472: Scaled oleuropein peracetylation procedure, GC–MS, LC–HRMS, 1H and 13C NMR

• spectra of new compounds, as well as calculation for green chemistry metrics. Acknowledgements This work was supported by the grant POR Calabria FSE 2007/2013, Asse IV "Capitale Umano", Obiettivo Operativo M.2., Piano d'azione 2011-2013- Department 11 "Cultura-Istruzione-Università-Ricerca-Innovazione

Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation

• Xiaofeng Zhang,
• Kenny Pham,
• Shuai Liu,
• Marc Legris,
• Alex Muthengi,
• Jerry P. Jasinski and
• Wei Zhang

Beilstein J. Org. Chem. 2016, 12, 2204–2210, doi:10.3762/bjoc.12.211

• Xiaofeng Zhang Kenny Pham Shuai Liu Marc Legris Alex Muthengi Jerry P. Jasinski Wei Zhang Center for Green Chemistry and Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, MA 02125, USA Department of Chemistry, Keene State College, 220 Main Street, Keene

Regiocontroled Pd-catalysed C5-arylation of 3-substituted thiophene derivatives using a bromo-substituent as blocking group

• Mariem Brahim,
• Hamed Ben Ammar,
• Jean-François Soulé and
• Henri Doucet

Beilstein J. Org. Chem. 2016, 12, 2197–2203, doi:10.3762/bjoc.12.210

• arylated thiophenes [17][18][19][20][21][22][23][24][25]. The method is very attractive in terms of green chemistry, because its major by-products are not metal salts but a base associated to HX, and synthesis of an organometallic derivative can be avoided. However, for C3-substituted thiophenes, arylation

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

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

• concentrations (Table 1, entries 2 and 3) allowing for a reduction in solvent volume, commensurate with the principles of green chemistry [46][47]. In attempts to further limit waste, we scanned a series of bases (see Supporting Information File 1); organic bases consistently performed more effectively and

The in situ generation and reactive quench of diazonium compounds in the synthesis of azo compounds in microreactors

• Faith M. Akwi and
• Paul Watts

Beilstein J. Org. Chem. 2016, 12, 1987–2004, doi:10.3762/bjoc.12.186

• principles of green chemistry [1][2] such as less hazardous chemical synthesis, efficient atom economy, reduction of waste produced, some alternative cleaner methods for the synthesis of azo dyes have been developed. These methods are however only representative of particular coupling agents and diazotized

Bridgehead vicinal diallylation of norbornene derivatives and extension to propellane derivatives via ring-closing metathesis

• Sambasivarao Kotha and
• Rama Gunta

Beilstein J. Org. Chem. 2016, 12, 1877–1883, doi:10.3762/bjoc.12.177

• refinement. S. K. thanks the Department of Science and Technology for the award of a J. C. Bose fellowship and Praj industries for Chair Professorship (Green Chemistry). R. G. thanks the University Grants Commission (UGC), New Delhi for the award of a research fellowship.

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

• Chemistry, Biology and Material Engineering, Suzhou University of Science and Technology, 1 Ke Rui Road, Suzhou, Jiangsu, 215009, P. R. China Department of Chemistry, Shanghai Key Laboratory of Green Chemistry and Chemical, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, P. R

Sustainable catalysis

• Nicholas J. Turner

Beilstein J. Org. Chem. 2016, 12, 1778–1779, doi:10.3762/bjoc.12.167

• Nicholas J. Turner School of Chemistry & Manchester Institute of Biotechnology, The University of Manchester, 131 Princess Street, M1 7DN, Manchester, United Kingdom 10.3762/bjoc.12.167 Keywords: green chemistry; sustainable catalysis; This focused collection of papers is devoted to recent

• developments in ‘green chemistry’, especially the applications of catalytic methods, involving both chemo- and biocatalysis. The development of catalytic processes is an important current theme in organic chemistry, since it aims to reduce the environmental impact of the industrial synthesis of chemicals and

• terms of safety and disposal of waste byproducts. Recently, many of these aspects of green chemistry have been the focus of the CHEM21 project (http://www.chem21.eu), funded by the Innovative Medicines Initiative, which is supported by the European Federation of Pharmaceutical Industries Association

Rearrangements of organic peroxides and related processes

• Ivan A. Yaremenko,
• Vera A. Vil’,
• Dmitry V. Demchuk and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162

• organocatalysts [262][263]. There are also Green chemistry approaches for Baeyer−Villiger oxidations based on enzyme-mediated processes, which are used for the preparation of chiral lactones. This type of biocatalysis is useful in synthetic chemistry and either isolated enzymes or living whole cells are applied