Catalyst-free synthesis of 4-acyl-NH-1,2,3-triazoles by water-mediated cycloaddition reactions of enaminones and tosyl azide

• Lu Yang,
• Yuwei Wu,
• Yiming Yang,
• Chengping Wen and
• Jie-Ping Wan

Beilstein J. Org. Chem. 2018, 14, 2348–2353, doi:10.3762/bjoc.14.210

• synthesis of 4-acyl-NH-1,2,3-triazoles has been accomplished with high efficiency through the cycloaddition reactions between N,N-dimethylenaminones and tosyl azide. This method is featured with extraordinary sustainability by employing water as the sole medium, free of any catalyst or additive

• present method benefits from unique sustainability not only due to the metal/additive-free cycloaddition reaction, but also by applying the completely green reaction medium water and mild reaction temperature. Scope of the water-mediated synthesis of 4-acyl-NH-1,2,3-triazoles. General conditions

Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry

• Michael K. Bogdos,
• Emmanuel Pinard and
• John A. Murphy

Beilstein J. Org. Chem. 2018, 14, 2035–2064, doi:10.3762/bjoc.14.179

• pharmaceutical industry. This type of chemistry has also demonstrated a high degree of sustainability, especially when organic dyes can be employed in place of often toxic and environmentally damaging transition metals. The sections are arranged according to the general class of the presented reactions and the

Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis

• Gwendal Grelier,
• Benjamin Darses and
• Philippe Dauban

Beilstein J. Org. Chem. 2018, 14, 1508–1528, doi:10.3762/bjoc.14.128

• iodoarenes, which are released in stoichiometric amounts in any reaction mediated by λ3- or λ5-iodanes. In parallel to the development of solid-supported reagents or reactions catalytic in iodine, a third strategy has emerged to address this issue in terms of sustainability. The atom-economy of

• reactions involving a step that enables the introduction of the iodoarene side-compound into the products. Various sequences combining oxidation reactions, nucleophilic additions, or aromatic couplings, thus, have been reported (Scheme 1b). In addition to address the issue of sustainability, this

• catalytic amount of dimethylethylenediamine. Linear diaryl-λ3-iodanes When compared to cyclic diaryl-λ3-iodanes, the linear analogues inherently raise a more challenging issue to address in terms of sustainability, particularly in the case of non-symmetrical reagents. As mentioned in the introduction, the

Nanoreactors for green catalysis

• M. Teresa De Martino,
• Loai K. E. A. Abdelmohsen,
• Floris P. J. T. Rutjes and
• Jan C. M. van Hest

Beilstein J. Org. Chem. 2018, 14, 716–733, doi:10.3762/bjoc.14.61

• sustainability and elegancy. Utilizing catalytic nanoreactors for greener reactions, for facilitating multistep synthetic pathways in one-pot procedures, is imperative with far-reaching implications in the field. This review is focused on the applications of some of the most used nanoreactors in catalysis

Latest development in the synthesis of ursodeoxycholic acid (UDCA): a critical review

• Fabio Tonin and
• Isabel W. C. E. Arends

Beilstein J. Org. Chem. 2018, 14, 470–483, doi:10.3762/bjoc.14.33

• . An approach that bears great promise is the biotransformation with non-pathogenic, easy-to-manage microorganisms, and their enzymes. Several chemical, chemoenzymatic and enzymatic routes have been proposed for the production of UDCA. In view of sustainability, instead of pursuing a step-wise approach

Mechanochemistry

• José G. Hernández

Beilstein J. Org. Chem. 2017, 13, 2372–2373, doi:10.3762/bjoc.13.234

• of achieving chemical reactivity under solvent-free conditions. Additionally, the utilization of mechanochemical technology can often further simplify the posterior work-up procedures, having a deeper impact on the sustainability of the global synthetic process (reduction of waste, lower energy

Synthesis of ergostane-type brassinosteroids with modifications in ring A

• Vladimir N. Zhabinskii,
• Darya A. Osiyuk,
• Yuri V. Ermolovich,
• Natalia M. Chaschina,
• Tatsiana S. Dalidovich,
• Miroslav Strnad and
• Vladimir A. Khripach

Beilstein J. Org. Chem. 2017, 13, 2326–2331, doi:10.3762/bjoc.13.229

• Foundation for Fundamental Research (projects X16K-057 and X17PM-040), and Ministry of Education, Youth and Sports of the Czech Republic through the National Program of Sustainability I (grant LO1204).

One-pot multistep mechanochemical synthesis of fluorinated pyrazolones

• Joseph L. Howard,
• William Nicholson,
• Yerbol Sagatov and
• Duncan L. Browne

Beilstein J. Org. Chem. 2017, 13, 1950–1956, doi:10.3762/bjoc.13.189

• Joseph L. Howard William Nicholson Yerbol Sagatov Duncan L. Browne School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, UK 10.3762/bjoc.13.189 Abstract Solventless mechanochemical synthesis represents a technique with improved sustainability metrics compared to

• inhibit future steps, e.g., by providing access to alternative reaction pathways, poisoning catalysts or altering the pH unfavourably [9]. With regards to mechanochemistry such processing serves to amplify the sustainability metrics by running back-to-back solventless reactions. Multistep mechanochemical

Framing major prebiotic transitions as stages of protocell development: three challenges for origins-of-life research

• Ben Shirt-Ediss,
• Sara Murillo-Sánchez and
• Kepa Ruiz-Mirazo

Beilstein J. Org. Chem. 2017, 13, 1388–1395, doi:10.3762/bjoc.13.135

• for the sustainability of any type of cell [7][8]. Furthermore, this more encompassing approach to life is fully congruent with other insights coming from investigations on reaction–diffusion processes in biology, which have revealed, since the pioneering work of Turing [9], the enormous potential of

BODIPY-based fluorescent liposomes with sesquiterpene lactone trilobolide

• Ludmila Škorpilová,
• Silvie Rimpelová,
• Michal Jurášek,
• Miloš Buděšínský,
• Jana Lokajová,
• Roman Effenberg,
• Petr Slepička,
• Tomáš Ruml,
• Eva Kmoníčková,
• Pavel B. Drašar and
• Zdeněk Wimmer

Beilstein J. Org. Chem. 2017, 13, 1316–1324, doi:10.3762/bjoc.13.128

• . Acknowledgements The authors thank for funding of this research to MŠMT (project MSMT No 20-SVV/2017, and project COST LD15012, a part of the COST Action CM1407) and Czech Science Foundation (GAČR) 14-04329S and the Czech Republic grants no. CZ.2.16/3.1.00/24503, LO1601, LO1304 (National Program of Sustainability

Biomimetic molecular design tools that learn, evolve, and adapt

• David A Winkler

Beilstein J. Org. Chem. 2017, 13, 1288–1302, doi:10.3762/bjoc.13.125

• features in a conceptual landscape are also employed. Sparse feature detection in vivo Detection of important features in the environment is critical for the long-term sustainability of life. For example, the roughly 100 million photoreceptors in a human retina cannot not directly transmit a picture to the

Automating multistep flow synthesis: approach and challenges in integrating chemistry, machines and logic

• Chinmay A. Shukla and
• Amol A. Kulkarni

Beilstein J. Org. Chem. 2017, 13, 960–987, doi:10.3762/bjoc.13.97

• important molecules [34]. Interdisciplinary research with long-term sustainability objectives and scientific interactions with industries can only help to find useful solutions. This implies that the compartmental approach followed by the synthesis community (which is necessary only while conceiving a new

Opportunities and challenges for the sustainable production of structurally complex diterpenoids in recombinant microbial systems

• Katarina Kemper,
• Max Hirte,
• Markus Reinbold,
• Monika Fuchs and
• Thomas Brück

Beilstein J. Org. Chem. 2017, 13, 845–854, doi:10.3762/bjoc.13.85

• and sustainability akin to total chemical synthesis, which is often associated with toxic metal-organic chemistry, low product yields and/or insufficient purity [19][20]. A promising route for sufficient supply of industrially relevant products or their precursors is the heterologous production of

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

• chemistry, and has elements of sustainability considering that in batch macroreactors, in order to avoid metal-assisted α-elimination, in situ quenching, an excess of reagents, and very low temperature are required [32][33]. Running the reaction in a flow system at −40 °C, by using residence times between

A chemoselective and continuous synthesis of m-sulfamoylbenzamide analogues

• Arno Verlee,
• Thomas Heugebaert,
• Tom van der Meer,
• Pavel I. Kerchev,
• Frank Van Breusegem and
• Christian V. Stevens

Beilstein J. Org. Chem. 2017, 13, 303–312, doi:10.3762/bjoc.13.33

• maintained. This effect is also linked to the optimized mixing conditions enabling higher temperatures without losing chemoselectivity, while increasing the reaction rate. This adds also significantly to an increased sustainability of the process since no cooling capacity is required. This process can be

Green chemistry

• Luigi Vaccaro

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

• . Turner [10], and “Organic synthesis using photoredox catalysis” by Axel G. Griesbeck [11], proving that green chemistry and sustainability can be approached from many different perspectives. The breadth of chemical and technological innovations makes the definition of novel metrics for the evaluation of

Electron-transfer-initiated benzoin- and Stetter-like reactions in packed-bed reactors for process intensification

• Anna Zaghi,
• Daniele Ragno,
• Graziano Di Carmine,
• Carmela De Risi,
• Olga Bortolini,
• Pier Paolo Giovannini,
• Giancarlo Fantin and
• Alessandro Massi

Beilstein J. Org. Chem. 2016, 12, 2719–2730, doi:10.3762/bjoc.12.268

• chemical and pharmaceutical industries facilitating the automation of the production processes with reduced costs and improved safety and sustainability [18][19][20][21]. Very recently, Monbaliu and co-workers described a convenient continuous-flow setup for the generation of common free NHCs under

Towards the development of continuous, organocatalytic, and stereoselective reactions in deep eutectic solvents

• Davide Brenna,
• Elisabetta Massolo,
• Alessandra Puglisi,
• Sergio Rossi,
• Giuseppe Celentano,
• Maurizio Benaglia and
• Vito Capriati

Beilstein J. Org. Chem. 2016, 12, 2620–2626, doi:10.3762/bjoc.12.258

• advantages in terms of reaction sustainability. In particular, the possibility to strongly reduce the amounts of organic solvent and the recyclability of the catalyst were demonstrated [23]. Moreover, in this approach, no structural modification of the precious chiral catalyst was necessary. A well-explored

The weight of flash chromatography: A tool to predict its mass intensity from thin-layer chromatography

• Freddy Pessel,
• Jacques Augé,
• Isabelle Billault and
• Marie-Christine Scherrmann

Beilstein J. Org. Chem. 2016, 12, 2351–2357, doi:10.3762/bjoc.12.228

• purification of products is very often omitted. For example, the mass of silica gel and eluents used are never mentioned, which prevents the reader from calculating MIp, and thus having the actual value of the E factor. The impact of chromatography on sustainability was recently discussed [9] and we propose

Robust C–C bonded porous networks with chemically designed functionalities for improved CO₂ capture from flue gas

• Damien Thirion,
• Joo S. Lee,
• Ercan Özdemir and
• Cafer T. Yavuz

Beilstein J. Org. Chem. 2016, 12, 2274–2279, doi:10.3762/bjoc.12.220

• Damien Thirion Joo S. Lee Ercan Ozdemir Cafer T. Yavuz Graduate School of Energy, Environment, Water, Sustainability (EEWS), Korea Advanced Institute of Science and Technology (KAIST), Guseong Dong, Yuseong Gu, Daejeon 305–701, Korea Department of Chemistry, Korea Advanced Institute of Science and

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

• terms of sustainability, applications and market value. In fact, dehydration of D-sorbitol (Scheme 1) produces anhydro sugar alcohols, including sorbitan (mono-anhydrosorbitol) and isosorbide (dianhydrosorbitol). Both these products have achieved commercial importance and can be used to synthesize

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

• sustainability of the process from an industrial point of view [44]. For the calculation of MI and MP the reaction work-up was included as a reaction step (see Supporting Information File 1) because the products obtained by the hydrolysis of the excess of Ac2O used, both as reaction reagent and solvent, are

• useful chemicals. The calculated values were good, thus demonstrating the versatility and sustainability of the process. Our prevision shows how the process remains reasonable in terms of mass productivity, ranging from 16% to 50%. Finally a scaled protocol extended to the maximum oven capacity was

Solvent-free synthesis of novel para-menthane-3,8-diol ester derivatives from citronellal using a polymer-supported scandium triflate catalyst

• Lubabalo Mafu,
• Ben Zeelie and
• Paul Watts

Beilstein J. Org. Chem. 2016, 12, 2046–2054, doi:10.3762/bjoc.12.193

• sustainability perspective, but clearly it is necessary to develop protocols that are as environmentally friendly and sustainable as possible. The terpene, citronellal (3,7-dimethyl-6-octenal, 1) is widely used as a feedstock material in the synthesis of fine chemicals such as menthol (2) and para-menthane-3,8

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

• reactions reported using aryl iodides can be linked to the use of DMF as a solvent [5]. In this context, the sustainability movement within pharmaceutical research and development strives to substitute solvents that have regulatory and environmental issues for those with a lower perceived risk. Indeed

• , solvent replacement has been designated a key research area with numerous pharmaceutical companies detailing their efforts towards a more sustainable solvent selection as part of their overall sustainability programmes [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23]. Based on its

Stereo- and regioselectivity of the hetero-Diels–Alder reaction of nitroso derivatives with conjugated dienes

• Lucie Brulíková,
• Aidan Harrison,
• Marvin J. Miller and
• Jan Hlaváč

Beilstein J. Org. Chem. 2016, 12, 1949–1980, doi:10.3762/bjoc.12.184