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

Mutagenic activity of quaternary ammonium salt derivatives of carbohydrates

• Barbara Dmochowska,
• Karol Sikora,
• Anna Woziwodzka,
• Jacek Piosik and
• Beata Podgórska

Beilstein J. Org. Chem. 2016, 12, 1434–1439, doi:10.3762/bjoc.12.138

• “green chemistry” solvents, and are considered as a good alternative for classical organic solvents. Among many applications, dissolving cellulose (which was impossible for common solvents), depolymerizing nonnatural polymers, and capturing CO2 appear particularly interesting [15]. Despite their unique

Iodine-mediated synthesis of 3-acylbenzothiadiazine 1,1-dioxides

• Long-Yi Xi,
• Ruo-Yi Zhang,
• Lei Shi,
• Shan-Yong Chen and
• Xiao-Qi Yu

Beilstein J. Org. Chem. 2016, 12, 1072–1078, doi:10.3762/bjoc.12.101

• Long-Yi Xi Ruo-Yi Zhang Lei Shi Shan-Yong Chen Xiao-Qi Yu Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China 10.3762/bjoc.12.101 Abstract An iodine-mediated synthesis of 3-acylbenzothiadizine 1,1-dioxides is

Cationic Pd(II)-catalyzed C–H activation/cross-coupling reactions at room temperature: synthetic and mechanistic studies

• Takashi Nishikata,
• Alexander R. Abela,
• Shenlin Huang and
• Bruce H. Lipshutz

Beilstein J. Org. Chem. 2016, 12, 1040–1064, doi:10.3762/bjoc.12.99

• intermediate, characterized by X-ray analysis. Roles of various additives in the stepwise process have also been studied. Keywords: arylation; cationic palladium; C–H functionalization; green chemistry; olefination; Introduction Transition metal-catalyzed, direct functionalization of aryl C–H bonds has made

A convenient route to symmetrically and unsymmetrically substituted 3,5-diaryl-2,4,6-trimethylpyridines via Suzuki–Miyaura cross-coupling reaction

• Dariusz Błachut,
• Joanna Szawkało and
• Zbigniew Czarnocki

Beilstein J. Org. Chem. 2016, 12, 835–845, doi:10.3762/bjoc.12.82

• , especially in water-based solvents, is important from the point of view of so-called “green chemistry” and also its economic efficiency [44][45]. In our hands, all attempts to carry out the reaction with both palladium acetate or palladium chloride gave the desired diarylated product 4 with unacceptable

Three new trixane glycosides obtained from the leaves of Jungia sellowii Less. using centrifugal partition chromatography

• Luíse Azevedo,
• Larissa Faqueti,
• Marina Kritsanida,
• Antonia Efstathiou,
• Despina Smirlis,
• Gilberto C. Franchi Jr,
• Grégory Genta-Jouve,
• Sylvie Michel,
• Louis P. Sandjo,
• Raphaël Grougnet and
• Maique W. Biavatti

Beilstein J. Org. Chem. 2016, 12, 674–683, doi:10.3762/bjoc.12.68

• complexity, and frequently have more advantageous ADME/T properties [18]. Compared to other chromatographic methods, centrifugal partition chromatography (CPC) is compatible with green chemistry criteria since it does not use any polluting solid support such as silica. Moreover, it allows the complete

A selective and mild glycosylation method of natural phenolic alcohols

• Mária Mastihubová and
• Monika Poláková

Beilstein J. Org. Chem. 2016, 12, 524–530, doi:10.3762/bjoc.12.51

• contract No. APVV-846-12, the Scientific Grant Agency of the Ministry of Education of Slovak Republic and Slovak Academy of Sciences (VEGA) under the project No. 2/0138/12 and the Research & Development Operational Programmes funded by the ERDF („Centre of Excellence on Green Chemistry Methods and

• Processes“, CEGreenI, Contract No. 26240120001 as well as „Amplification of the Centre of Excellence on Green Chemistry Methods and Processes“, CEGreenII, Contract No. 26240120025). The authors thank I. Uhliariková for NMR measurements, S. Bekešová and S. Vlčková for mass measurements.

Synthesis of bi- and bis-1,2,3-triazoles by copper-catalyzed Huisgen cycloaddition: A family of valuable products by click chemistry

• Zhan-Jiang Zheng,
• Ding Wang,
• Zheng Xu and
• Li-Wen Xu

Beilstein J. Org. Chem. 2015, 11, 2557–2576, doi:10.3762/bjoc.11.276

• investigated and recognized as an epoch-making progress in organic synthesis and green chemistry [11][12][13][14][15]. After many years of research, it was proven that the Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC reaction) could be performed under various conditions according to the need of click

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

• UMR6226 CNRS, Institut des Sciences Chimiques de Rennes, Université de Rennes 1, Organometallics: Materials and Catalysis, Centre for Catalysis and Green Chemistry, Campus de Beaulieu, 35042 Rennes Cedex, France Charles University in Prague, Faculty of Science, Department of Physical and Macromolecular

Recent applications of ring-rearrangement metathesis in organic synthesis

• Sambasivarao Kotha,
• Milind Meshram,
• Priti Khedkar,
• Shaibal Banerjee and
• Deepak Deodhar

Beilstein J. Org. Chem. 2015, 11, 1833–1864, doi:10.3762/bjoc.11.199

• have covered literature that appeared during the last seven years (2008–2014). Keywords: Diels–Alder chemistry; green chemistry; natural products; olefin metathesis; polycycles; ring-rearrangement metathesis; Introduction Transition metal–carbene complexes (Figure 1) introduced during the last two

An efficient synthesis of N-substituted 3-nitrothiophen-2-amines

• Sundaravel Vivek Kumar,
• Shanmugam Muthusubramanian,
• J. Carlos Menéndez and
• Subbu Perumal

Beilstein J. Org. Chem. 2015, 11, 1707–1712, doi:10.3762/bjoc.11.185

• goals of green chemistry [32]. In this context, we wish to report herein a new and efficient synthesis of 3-nitro-N-aryl/alkylthiophen-2-amines based on domino reactions between α-nitroketene N,S-aryl/alkylaminoacetals and 1,4-dithiane-2,5-diol, the dimer of 2-mercaptoacetaldehyde (Scheme 2). This work

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

• Yuri A. Rulev Zalina Gugkaeva Victor I. Maleev Michael North Yuri N. Belokon Nesmeyanov Institute of Organoelement Compounds, Moscow 19991, Russia Green Chemistry Centre of Excellence, Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK 10.3762/bjoc.11.176 Abstract Two new