Green Chemistry Blog

The latest issue of Green Chemistry is now available to read online.

The front cover of issue 9 features work by Tomislav Frišĉić from the University of Cambridge (UK) and McGill University (Canada) and colleagues from Croatia, the UK and USA.  The authors discuss the concept of a solvent-free research laboratory which would eliminate the use of solvents for both chemical synthesis and the structural characterization.  The team used the mechanochemical click coupling of isothiocyanates and amines as the model reaction using an electrical, digitally controllable laboratory mill.  49 different thiourea derivatives were synthesized and all products were characterised by X-ray diffraction and solid-state NMR spectroscopy.

A model for a solvent-free synthetic organic research laboratory: click-mechanosynthesis and structural characterization of thioureas without bulk solvents, Vjekoslav Štrukil, Marina D. Igrc, László Fábián, Mirjana Eckert-Maksić, Scott L. Childs, David G. Reid, Melinda J. Duer, Ivan Halasz, Cristina Mottillo and Tomislav Friščić, Green Chem., 2012, 14, 2462-2473

The inside front cover of this issue highlights work by Chan Beum Park and co-workers from KAIST and Seoul National University, Korea, who report the synthesis of graphene-wrapped CuO hybrid materials by CO₂mineralization.  These materials were created from CoCO3 microspheres mineralized on graphene oxide nanosheets and were shown to be promising materials for lithium ion batteries.  The hybrid materials demonstrated greatly enhanced stability and recyclability of the CuO anode for the Li ion batteries.

Synthesis of graphene-wrapped CuO hybrid materials by CO₂ mineralization, Jong Wan Ko, Sung-Wook Kim, Jihyun Hong, Jungki Ryu  Kisuk Kang and Chan Beum Park, Green Chem., 2012, 14, 2391-2394

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The latest issue of Green Chemistry is now available online!

The front cover of issue 8 features work by Matthew Fuchter and co-workers from Imperial College London and Pfizer Ltd in Sandwich.  The team developed a route to give allylic alcohols from α,β-unsaturated ketones using calcium triflate to replace cerium(III) chloride.  This procedure also accomplished the regioselective 1,2-reduction of challenging α,β-unsaturated ketones such as 2-cyclopentenone with very good selectivity, and is suitable for the stereoselective reduction of α,β-aziridinyl ketones.

Lanthanide replacement in organic synthesis: Luche-type reduction of α,β-unsaturated ketones in the presence of calcium triflate, Nina V. Forkel, David A. Henderson and Matthew J. Fuchter, Green Chem., 2012, 14, 2129-2132.

The inside front cover highlights work by Man Bock Gu and colleagues from Korea University in Seoul, who report the carbonic anhydrase-assisted formation of biomineralized calcium carbonate crystalline composites (CCCCs).  These materials were shown to be effective biocatalysts retaining 43% of the free carbonic anhydrase esterase activity.  The catalysts were stable for more than 50 days at room temperature, could be recovered easily using magnet-based separation and retained their activity over 10 repeated usages.

Carbonic anhydrase assisted calcium carbonate crystalline composites as a biocatalyst, Ee Taek Hwang, Haemin Gang, Jinyang Chung and Man Bock Gu, Green Chem., 2012, 14, 2216-2220

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Screenshot of the Green Solvents App for iPad

Several new mobile applications (Apps) have been recently released for the Apple iOS platform which incorporate green chemistry concepts. This represents a highly novel way to communicate science and bring green chemistry to a bigger audience, which has not previously been appreciated. We certainly sense there is an untapped audience for these types of applications due to the large number of people who now own a mobile device across all demographics. Green Chemistry related information is generally proprietary and papers on the topic are commonly behind paywalls. Making the information freely available or at low cost is a paradigm shift.

For example, a recent consortium organized by the American Chemical Society Green Chemistry Institute^TM (ACS GCI) Pharmaceutical Roundtable¹ currently involves 14 pharmaceutical companies, and has developed a solvent selection guide that is publicly available on their website in the form of a PDF file.² We have made this solvent selection guide more accessible in the form of a free app called Green Solvents.^{3, 4} It is delivered as a simple structure look-up guide incorporating all of the selection criteria from the ACS GCI and, in addition, having links out to other useful resources (ChemSpider ^5-7 etc.). This app, like most free apps, has a small banner advertisement which does not detract from the content of the app or its usability on a mobile device. Importantly this App was not funded by the ACS or any other organization.

Screenshot of the Open Drug Discovery Teams App for iPad

Creating the Green Solvents app has also motivated the addition of the process mass intensity (PMI) calculation⁸ (which is another green chemistry feature), into the Yield101 app⁹. A third recently developed mobile app connected to green chemistry is the Open Drug Discovery Teams (ODDT) app^{10, 11}. ODDT is a free mobile app intended as a research topic aggregator of science data collected from various sources on the internet such as Twitter and Google Alerts. It exists to facilitate interdisciplinary teamwork and deliver access to information that is highly relevant and focused on the topic areas of interest. Research topics include areas of chemistry and adjacent molecule-oriented biomedical sciences, with an emphasis on those which are most amenable to open research at present. We have focused on green chemistry as a topic due to its potential importance for scientists involved in drug discovery for rare and neglected diseases. There is high attrition in drug discovery, so many compounds will need to be made but only a very small fraction will make it into the clinic and, far less, into the marketplace. It is therefore important to design a green process as early as possible when the cost is lower and the quantities of chemicals made are relatively small compared to when they are dramatically scaled up for manufacturing. We feel these global neglected and rare disease researchers would benefit greatly from being informed about green chemistry principles early on and that this has not been considered by any of the major organizations driving green chemistry initiatives. This app has also been used to visualize the ACS GCI solvent selection guide in a different format as it was Tweeted out to reach an even wider audience for those following the hashtag #greenchemistry. To date we are the only researchers that have created and used mobile apps to communicate green chemistry concepts. We feel this is an area that is ripe for expansion to further educate scientists.

Sean Ekins^*
Collaborations in Chemistry, 5616 Hilltop Needmore Road, Fuquay-Varina, NC 27526, U.S.A.
Alex M. Clark
Molecular Materials Informatics, 1900 St. Jacques #302, Montreal, Quebec, Canada H3J 2S1
Antony J. Williams
Royal Society of Chemistry, 904 Tamaras Circle, Wake Forest, NC 27587, U.S.A. 

1. American Chemical Society Green Chemistry Institute^TM Pharmaceutical Roundtable www.acs.org/gcipharmaroundtable
2. Solvent selection guide. http://surveys.acs.org/se.ashx?s=04BD76CC0E5496A7
3. Ekins, S. Green Solvents: From Idea to App in 3 Days. http://www.slideshare.net/ekinssean/green-solvents-app
4. Clark, A. M. Green Solvents. http://www.scimobileapps.com/index.php?title=Green_Solvents
5. ChemSpider. www.chemspider.com
6. Pence, H. E.; Williams, A. J. ChemSpider: An Online Chemical Information Resource. J Chem Educ 2010, 87, 1123-1124.
7. Williams, A. J. Public chemical compound databases. Curr Opin Drug Discov Devel 2008, 11, 393-404.
8. ACS GCI Pharmaceutical Roundtable. http://portal.acs.org/portal/acs/corg/content?_nfpb=true&_pageLabel=PP_TRANSITIONMAIN&node_id=1422&use_sec=false&sec_url_var=region1&__uuid=46aca9b6-a985-42cd-a534-7d6cabf892a7
9. Clark, A. M. Yield-101. http://www.scimobileapps.com/index.php?title=Yield101
10. Ekins, S.; Clark, A. M.; Williams, A. J. Open Drug Discovery Teams: A Chemistry Mobile App for Collaboration. Molecular Informatics 2012, In Press.
11. Philippidis, A. App connects rare disease researchers to data. http://www.genengnews.com/insight-and-intelligenceand153/app-connects-rare-disease-researchers-to-data/77899637/

The latest issue of Green Chemistry is now available online and is packed with the usual high quality research.

The front cover of this issue showcases the Critical Review by Raffael Wende and Peter Schreiner from Justus-Liebig University in Giessen, Germany, on the evolution of asymmetric organocatalysis.  The authors focus on the recent developments into organomulticatalysis, i.e.the combination of several distinct organocatalysts enabling consecutive reactions to be conducted in one pot. Schreiner and Wende also look at multicatalysts – catalysts with a single backbone with several independent, orthogonally reactive moieties attached.  The review highlights the impressive advantages of asymmetric organomulticatalysis and look at the development that have occurred from it’s very beginnings to the latest multicatalyst systems. 

Evolution of asymmetric organocatalysis: multi- and retrocatalysis, Raffael C. Wende and Peter R. Schreiner, Green Chem., 2012, 14, 1821-1849

The inside front cover highlights work by Hong Liu and colleagues from the Shanghai Institute of Materia Medica, Chinese Academy of Sciences, China, who reported the gold catalysed synthesis of fused polycyclic indoles.  Substituted 2-(1H-indol-1-yl)alkylamines were reacted with alkynoic acids in water under microwave irradiation for 30 min giving the products in excellent yields.  This procedure proceeds with high atom economy and leads to the generation of two rings, together with the formation of one new C-C bond and two new C-N bonds in a single operation. 

Gold-catalyzed tandem reaction in water: an efficient and convenient synthesis of fused polycyclic indoles, Enguang Feng, Yu Zhou, Fei Zhao, Xianjie Chen, Lei Zhang, Hualiang Jiang and Hong Liu, Green Chem., 2012, 14, 1888-1895

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