Matsuda–Heck reaction with arenediazonium tosylates in water

• Ksenia V. Kutonova,
• Marina E. Trusova,
• Andrey V. Stankevich,
• Pavel S. Postnikov and
• Victor D. Filimonov

Beilstein J. Org. Chem. 2015, 11, 358–362, doi:10.3762/bjoc.11.41

• Chemistry of New Materials NAS Belarus, 220141, Minsk, Belarus Department of General and Inorganic Chemistry, National Research Tomsk Polytechnic University, 634050 Tomsk, Russia 10.3762/bjoc.11.41 Abstract An environmentally friendly Matsuda–Heck reaction with arenediazonium tosylates has been developed

• ]. In this work, we present a fast, environmentally friendly, low palladium loading method of the Matsuda–Heck arylation of the different alkenes with ADT in water under microwave irradiation. Results and Discussion Our preliminary study was dedicated to the optimization of the alkene arylation

The Shono-type electroorganic oxidation of unfunctionalised amides. Carbon–carbon bond formation via electrogenerated N-acyliminium ions

• Alan M. Jones and
• Craig E. Banks

Beilstein J. Org. Chem. 2014, 10, 3056–3072, doi:10.3762/bjoc.10.323

• having the nucleophile solid-supported [53]. The use of ionic liquids as a green electrolyte/solvent [54] and using solar power to provide the electrical current [55] are some of the recent additions to make electrosynthesis even more environmentally friendly. Further advances have been made using

First chemoenzymatic stereodivergent synthesis of both enantiomers of promethazine and ethopropazine

• Paweł Borowiecki,
• Daniel Paprocki and
• Maciej Dranka

Beilstein J. Org. Chem. 2014, 10, 3038–3055, doi:10.3762/bjoc.10.322

• chiral drugs has emerged as an important factor in efficacy and safety of their application [1][2][3]. Thus, the development of an effective, inexpensive and environmentally friendly method for the formulation of single enantiomers still remains a challenging task for organic chemists. Nowadays

Come-back of phenanthridine and phenanthridinium derivatives in the 21st century

• Lidija-Marija Tumir,
• Marijana Radić Stojković and
• Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2930–2954, doi:10.3762/bjoc.10.312

• (52–99%, Scheme 5). Important advantages of the method are environmentally friendly and easily removable byproducts (CO2 and ethanol or phenol), and the negligible impact of the electronic nature of the substituent on the reaction [18]. The oxidative PhI(OAc)2-mediated cyclization of 2

• -substituted on the phenyl side-rings by a large variety of substituents, as well as stereo- and regioselectivity (particularly for the bulky groups). Nevertheless, due to the most common metal catalyst (palladium) this method is significantly more expensive and less environmentally friendly than radical-based

• methods. To address these disadvantages, in the last decade particular attention was given to the replacement of the expensive palladium catalyst, for instance by iron [37]. However, major impact was made by introduction of the cheap and environmentally friendly intramolecular homolytic aromatic

Recent advances in the electrochemical construction of heterocycles

• Robert Francke

Beilstein J. Org. Chem. 2014, 10, 2858–2873, doi:10.3762/bjoc.10.303

• considered to be a safe and environmentally friendly methodology [21][22][23][24][25]. A further interesting feature is that electrochemical reactions are feasible under very mild conditions; since the reaction rate is determined by the electrode potential, reactions with high activation energies can be

A green approach to the synthesis of novel phytosphingolipidyl β-cyclodextrin designed to interact with membranes

• Yong Miao,
• Florence Djedaïni-Pilard and
• Véronique Bonnet

Beilstein J. Org. Chem. 2014, 10, 2654–2657, doi:10.3762/bjoc.10.278

• using a green methodology. Reactions using greener and safer catalysts with more environmentally friendly purification solvents were performed. Four unreported mono-substituted cyclodextrins bearing a phytosphingolipidyl chain and a fatty acid chain (C10, C12, C14 and C18) were successfully obtained

• time in cyclodextrin chemistry via solvent-free substitution of aminocyclodextrin followed by the use of a new, more environmentally friendly peptide coupling agent known as COMU (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate). Finally, by optimized

Electrocarboxylation: towards sustainable and efficient synthesis of valuable carboxylic acids

• Roman Matthessen,
• Jan Fransaer,
• Koen Binnemans and
• Dirk E. De Vos

Beilstein J. Org. Chem. 2014, 10, 2484–2500, doi:10.3762/bjoc.10.260

• promising technology for environmentally friendly chemical processes [26]. The electroreduction of CO2 can be applied for the synthesis of fuels like formic acid [27], methanol [28] or methane [29] via two-, six- and eight-electron reductions, respectively (Scheme 2). This way electric energy from periodic

• compounds that are valuable. This way a combined electrochemical yield, i.e., the fraction of supplied current going to the desired reaction, is achieved, reducing energy consumption and reaction time. This methodology is very environmentally friendly since there is no generation of toxic wastes, electrical

• [41][42]. Hydrogen formation can be limited by usage of cathode materials with high hydrogen overvoltage like lead and mercury, or more environmentally friendly tantalum and zinc [43]. In order to minimize other side reactions a cation exchange membrane (CEM) is necessary, allowing different

Oxidative phenylamination of 5-substituted 1-hydroxynaphthalenes to N-phenyl-1,4-naphthoquinone monoimines by air and light “on water”

• Julio Benites,
• Juan Meléndez,
• Cynthia Estela,
• David Ríos,
• Luis Espinoza,
• Iván Brito and
• Jaime A. Valderrama

Beilstein J. Org. Chem. 2014, 10, 2448–2452, doi:10.3762/bjoc.10.255

• radiation; Introduction The growing demand for the application of environmentally friendly technologies has led, in the last decades, to a great deal of research effort to develop low-impact alternative synthetic methods as well as to replace toxic and harmful solvents by more environmentally benign ones

Pd/C-catalyzed aerobic oxidative esterification of alcohols and aldehydes: a highly efficient microwave-assisted green protocol

• Marina Caporaso,
• Giancarlo Cravotto,
• Spyros Georgakopoulos,
• George Heropoulos,
• Katia Martina and
• Silvia Tagliapietra

Beilstein J. Org. Chem. 2014, 10, 1454–1461, doi:10.3762/bjoc.10.149

• on the catalytic performance of Au [21][22][23][24][25][26], Ru [27][28][29], Ir [30] and Pd [31][32][33][34][35]. Moreover, the search for new, less expensive and environmentally friendly catalysts has attracted a great deal of interest because of the limited availability and high price of noble

• interfaces and surfaces NIS, University of Turin, Via P. Giuria 7–9, 10125 Torino, Italy Institute of Biology, Medicinal Chemistry and Biotechnology, National Hellenic Research Foundation, 48. Vas. Constantinou Ave., 11635 Athens, Greece 10.3762/bjoc.10.149 Abstract We herein describe an environmentally

• friendly microwave-assisted oxidative esterification of alcohols and aldehydes in the presence of molecular oxygen and a heterogeneous catalysis (Pd/C, 5 mol %). This efficient and ligandless conversion procedure does not require the addition of an organic hydrogen acceptor. The reaction rate is strongly

Synthesis of chiral N-phosphoryl aziridines through enantioselective aziridination of alkenes with phosphoryl azide via Co(II)-based metalloradical catalysis

• Jingran Tao,
• Li-Mei Jin and
• X. Peter Zhang

Beilstein J. Org. Chem. 2014, 10, 1282–1289, doi:10.3762/bjoc.10.129

• -containing aziridines, producing nitrogen gas as the only and also environmentally friendly byproduct. Chiral phosphorylated aziridines and their derivatives have been demonstrated with pharmaceutical and other important synthetic applications. In addition to the fundamental and practical significance of the

Visible-light photoredox catalyzed synthesis of pyrroloisoquinolines via organocatalytic oxidation/[3 + 2] cycloaddition/oxidative aromatization reaction cascade with Rose Bengal

• Carlos Vila,
• Jonathan Lau and
• Magnus Rueping

Beilstein J. Org. Chem. 2014, 10, 1233–1238, doi:10.3762/bjoc.10.122

• have very important qualities such as being inexpensive, environmentally friendly and easy to handle. As a part of our ongoing research on photoredox catalysis [62][63][64][65][66][67][68][69][70][71][72], we herein present a synthesis of pyrrolo[2,1-a]isoquinolines through an oxidation/[3+2

Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp Trichogramma turkestanica

• Danny Geerdink,
• Jeffrey Buter,
• Teris A. van Beek and
• Adriaan J. Minnaard

Beilstein J. Org. Chem. 2014, 10, 761–766, doi:10.3762/bjoc.10.71

• reason to study these tiny wasps is their possible application in an environmentally friendly way of crop protection [5]. After copulation, the female wasp deposits the fertilized eggs inside the eggs of a host insect, which is used as a food source for the hatched wasps. Biological studies have revealed

Integration of enabling methods for the automated flow preparation of piperazine-2-carboxamide

• Richard J. Ingham,
• Claudio Battilocchio,
• Joel M. Hawkins and
• Steven V. Ley

Beilstein J. Org. Chem. 2014, 10, 641–652, doi:10.3762/bjoc.10.56

• via a number of different approaches but the most environmentally friendly procedure is the hydration of nitriles [19]. Although this is generally considered to be a simple transformation, there are some inherent problems with the standard techniques of hydrolysis [20]. Further to our previous work

Visible-light photoredox catalysis enabled bromination of phenols and alkenes

• Yating Zhao,
• Zhe Li,
• Chao Yang,
• Run Lin and
• Wujiong Xia

Beilstein J. Org. Chem. 2014, 10, 622–627, doi:10.3762/bjoc.10.53

• several drawbacks such as toxic reagents, harsh conditions, low yields, and low chemo- and regioselectivity. Hence, the development of an environmentally friendly methodology for the bromination of phenols with high chemoselectivity under mild and operationally simple conditions is still appealing

Silica: An efficient catalyst for one-pot regioselective synthesis of dithioethers

• Samir Kundu,
• Babli Roy and
• Basudeb Basu

Beilstein J. Org. Chem. 2014, 10, 26–33, doi:10.3762/bjoc.10.5

• environmentally friendly and sustainable [32][33][34][35][36]. Mesoporous inorganic oxides, which often facilitate various organic reactions, are considered suitable to promote eco-friendly chemical processes [36]. Organic reactions with a high selectivity under eco-friendly and sustainable conditions are

Continuous-flow Heck synthesis of 4-methoxybiphenyl and methyl 4-methoxycinnamate in supercritical carbon dioxide expanded solvent solutions

• Phei Li Lau,
• Ray W. K. Allen and
• Peter Styring

Beilstein J. Org. Chem. 2013, 9, 2886–2897, doi:10.3762/bjoc.9.325

• biphasic mode using a mixture of solvents, such as ethylene glycol and toluene [8]. The drive to carry out reactions in environmentally benign media also led to studies being carried out in “green” (environmentally friendly) solvents, such as aqueous media, some supercritical fluids (SCFs), ionic liquids

Biosynthesis of rare hexoses using microorganisms and related enzymes

• Zijie Li,
• Yahui Gao,
• Hideki Nakanishi,
• Xiaodong Gao and
• Li Cai

Beilstein J. Org. Chem. 2013, 9, 2434–2445, doi:10.3762/bjoc.9.281

• -rhamnitol) which was subsequently oxidized by Enterobacter aerogenes IK7 to afford the rare sugar 1-deoxy-L-fructose. The whole process was performed in an environmentally friendly fashion. II. Biosynthesis of rare aldohexoses D-Allose D-Allose is the C-3 epimer of D-glucose or the aldo/keto-isomer of D

• enzyme-catalyzed reactions are often highly enantioselective and regioselective. In addition, enzymatic reactions are usually performed under mild conditions and are environmentally friendly. However, two major challenges remain in this endeavor: 1) microorganisms and related enzymes presently applied in

Silica sulfuric acid: a reusable solid catalyst for one pot synthesis of densely substituted pyrrole-fused isocoumarins under solvent-free conditions

• Sudipta Pathak,
• Kamalesh Debnath and
• Animesh Pramanik

Beilstein J. Org. Chem. 2013, 9, 2344–2353, doi:10.3762/bjoc.9.269

• the synthesis of pyrrole-fused isocoumarins with the help of green methodology, so far. Therefore, the development of an environmentally friendly and safer reaction methodology following the green chemistry principles is essential for the synthesis of pyrrole-fused isocoumarins. The employment of a

• the synthetic route ‘‘benign by design’’. This is the first report, in which a rearrangement reaction has been carried out on the solid surface of SSA. Overall this greener and environmentally friendly method may attract the fellow chemists in chemical and pharmaceutical industries for the synthesis

Coupling of C-nitro-NH-azoles with arylboronic acids. A route to N-aryl-C-nitroazoles

• Marta K. Kurpet,
• Aleksandra Dąbrowska,
• Małgorzata M. Jarosz,
• Katarzyna Kajewska-Kania,
• Nikodem Kuźnik and
• Jerzy W. Suwiński

Beilstein J. Org. Chem. 2013, 9, 1517–1525, doi:10.3762/bjoc.9.173

• lower toxicity, easier to process and environmentally friendly. Next the catalytic activity of the copper salts was screened. Most known reports concerning N-arylation focus on Cu(OAc)2 salt [21][22], complexes of Cu(II) with different ligands [23][36], and heterocyclic copper-based catalysts [25][37

Metal-free aerobic oxidations mediated by N-hydroxyphthalimide. A concise review

• Lucio Melone and
• Carlo Punta

Beilstein J. Org. Chem. 2013, 9, 1296–1310, doi:10.3762/bjoc.9.146

• organocatalyst. Once reached, this final goal, combined with the use of molecular oxygen as stoichiometric oxidant under mild operative conditions, would definitely open the way towards much more cost-effective and environmentally friendly oxidative processes. Mediators of laccase. Catalytic role of NHPI in the

A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions

• Murugan Sathishkumar,
• Sangaraiah Nagarajan,
• Poovan Shanmugavelan,
• Murugan Dinesh and
• Alagusundaram Ponnuswamy

Beilstein J. Org. Chem. 2013, 9, 689–697, doi:10.3762/bjoc.9.78

• environmentally friendly methodologies for the synthesis of 2-iminothiazolidin-4-ones is worth attempting. In this regard, and in continuation of our recent reports on the solvent-free synthesis of amides [19][20], thioamides [21], cyclic imides [22], thiazolidin-4-ones [23], spirothiazolidin-4-ones [24], 1,2,3

NHC-catalysed highly selective aerobic oxidation of nonactivated aldehydes

• Lennart Möhlmann,
• Stefan Ludwig and
• Siegfried Blechert

Beilstein J. Org. Chem. 2013, 9, 602–607, doi:10.3762/bjoc.9.65

• of aldehydes to the corresponding acids or esters. The reaction proceeds under metal-free conditions by using N-heterocyclic carbenes as organocatalysts in combination with environmentally friendly oxygen as the terminal oxidation agent. Keywords: aerobic oxidation; chemoselective oxidation; metal

• ) for example can nowadays be gained directly from the conversion of biomass and thereby became an attractive synthesis unit in modern "green" chemistry [32]. Hence, further cheap and environmentally friendly selective transformations are of great interest. However, only a few methods have been

Influence of cyclodextrin on the solubility and the polymerization of (meth)acrylated Triton^® X-100

• Melanie Kemnitz and
• Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 2176–2183, doi:10.3762/bjoc.8.245

• . Water is an environmentally friendly and favorable solvent. The molecular weights, LCSTs and hydrodynamic diameters of the resulting polymers prepared in water are similar to those of the uncomplexed model polymers, which were synthesized in DMF (8 and 9). As an important result, it was possible to

Cyclodextrin-based nanosponges as drug carriers

• Francesco Trotta,
• Marco Zanetti and
• Roberta Cavalli

Beilstein J. Org. Chem. 2012, 8, 2091–2099, doi:10.3762/bjoc.8.235

• mechanical strength than activated carbon and are not affected by dust formation during application. Finally, they can be reused indefinitely after simple washing with an environmentally friendly solvent, such as ethanol. Nanosponges can be used as supports for catalysis applications. One important result

Polysiloxane ionic liquids as good solvents for β-cyclodextrin-polydimethylsiloxane polyrotaxane structures

• Narcisa Marangoci,
• Rodinel Ardeleanu,
• Laura Ursu,
• Constanta Ibanescu,
• Maricel Danu,
• Mariana Pinteala and
• Bogdan C. Simionescu

Beilstein J. Org. Chem. 2012, 8, 1610–1618, doi:10.3762/bjoc.8.184

• interactions. The structure is stable in the 20 to 80 °C domain as proved by the oscillatory and rotational rheological tests. Keywords: cyclodextrins; imidazolium salt; ionic liquid; polyrotaxanes; polysiloxanes; Introduction Ionic liquids (ILs) are environmentally friendly solvents with great potential for