Synthesis of tetrazines from gem-difluoroalkenes under aerobic conditions at room temperature

Synthesis of tetrazines from gem-difluoroalkenes under aerobic conditions at room temperature

Green Chem., 2017, Advance Article
DOI: 10.1039/C6GC03494B, Paper
Zheng Fang, Wen-Li Hu, De-Yong Liu, Chu-Yi Yu, Xiang-Guo Hu
A procedure for the synthesis of tetrazines from gem-difluoroalkenes under aerobic conditions has been developed.

Synthesis of tetrazines from gem-difluoroalkenes under aerobic conditions at room temperature

Zheng Fang,a   Wen-Li Hu,a   De-Yong Liu,a  Chu-Yi Yuab and   Xiang-Guo Hu*a  
*Corresponding authors
aNational Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, P. R. China
E-mail: huxiangg@iccas.ac.cn
bBeijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
Green Chem., 2017, Advance Article

DOI: 10.1039/C6GC03494B, http://pubs.rsc.org/en/Content/ArticleLanding/2017/GC/C6GC03494B?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

An efficient and green procedure for the synthesis of tetrazines has been developed based on an old chemistry reported by Carboni in 1958. Both symmetric and asymmetric 3,6-disubstituted 1,2,4,5-tetrazines can be obtained in moderate to high yields from the corresponding gem-difluoroalkenes under aerobic conditions at room temperature. This work represents a rare example that ambient air is utilized as an oxidant for the synthesis of tetrazines.
Synthesis of symmetric 3,6-dialkyl-1,2,4,5−tetrazine(3a−3h)
To a solution of 1,1−difluoroalkenes (1a, 50 mg, 0.27 mmol) in N,N-dimethylformide (DMF,5 mL) was added hydrazine (80%, 35 mg, 1.35 mmol). After stirring at room temperature for 4−6 hours, saturated ammonium chloride (20 mL) was added and the reaction mixture was extracted with dichloromethane (10 mL×3). The organic layer was combined, dried with anhydrous sodium sulfate. The solvent was concentrated and the crude product was dissolved in a suspension of Ethyl Acetate(5 mL) and 10% potassium carbonate solution(wt%, 5 mL) and stirred at room temperature for 24h under air atomerspere until the organic layer turned into amaranth obviously. The organic layer was collected, dried with anhydrous sodium sulfate. The crude product was purified by flash column chromatography[silica gel(#100–200), toluene] to afford the pure 1,2,4,5−tetrazines(3a−3h).
3,6−bis([1,1’−biphenyl]−4−ylmethyl)−1,2,4,5−tetra zine (3a).
str1
(41 mg, 83%).
purple solid; m.p. 200−202°C;
IR(KBr) nmax/cm−1 2924, 2850, 1488, 1451, 1432, 1388, 851, 750;
1 H NMR (400 MHz, CDCl3) 7.55−7.33 (m, 18H), 4.65 (s, 4H).
13C NMR (100 MHz, CDCl3) δ 169.2, 140.6, 140.4, 134.8, 129.7, 128.8, 127.6, 127.4, 127.1, 40.9;
HRMS (ESI): calcd. for C28H22N4 [M+H]+ 415.19172, found 415.19124.

///////tetrazines,  gem-difluoroalkenes, aerobic conditions, room temperature

Photobiocatalytic alcohol oxidation using LED light sources

Green Chemistry International

Photobiocatalytic alcohol oxidation using LED light sources

Oxidative lactonization of meso-3-methyl-1,5-pentanediol to (S)-4-methyltetrahydro-2H-pyran-2-one using horse liver alcohol dehydrogenase (HLADH) and photocatalytic, aerobic regeneration of NAD+.

Green Chem., 2017, 19,376-379
DOI: 10.1039/C6GC02008A, Communication
Open Access Open Access
Creative Commons Licence  This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
M. Rauch, S. Schmidt, I. W. C. E. Arends, K. Oppelt, S. Kara, F. Hollmann
The photocatalytic oxidation of NADH using a flavin photocatalyst and a simple blue LED light source is reported.

Photobiocatalytic alcohol oxidation using LED light sources

M. Rauch,a  S. Schmidt,a  I. W. C. E. Arends,a  K. Oppelt,b  S. Karac and  F. Hollmann*a  
*Corresponding authors
aDepartment of Biotechnology, Delft University of Technology, van der Maasweg 9, 2629HZ Delft, The Netherlands
E-mail: f.hollmann@tudelft.nl
b

View original post 484 more words

Asymmetric synthesis of (S)-phenylacetylcarbinol – closing a gap in C–C bond formation

Green Chemistry International

Graphical abstract: Asymmetric synthesis of (S)-phenylacetylcarbinol – closing a gap in C–C bond formation

image file: c6gc01803c-f3.tif
Fig. 3 Stereoselectivities of the new ApPDC-variants for the synthesis of (S)-PAC. The different variants were tested as wet cells, crude cell extracts, and purified enzymes. Reaction conditions: wet cells – 20 mM benzaldehyde; 200 mM pyruvate; 50 mM KPi-buffer (pH 6.5), 2.5 mM MgSO4; 0.1 mM ThDP; 20 °C; 800 rpm, 800 μL reaction volume in 1.5 mL closed glass vials, whole cell catalyst concentration of 50 mg mL−1. Crude cell extract – 20 mM benzaldehyde; 200 mM pyruvate; 50 mM KPi-buffer (pH 6.5), 2.5 mM MgSO4; 0.1 mM ThDP; 20 °C; 800 rpm, 500 μL reaction volume in a 96-well sheet; see ESI chapter 2.1.4–2.1.5 for the catalyst concentration. Purified enzyme – 40 mM benzaldehyde; 200 mM pyruvate; 50 mM KPi-buffer with three different pH values, 2.5 mM MgSO4; 0.1 mM ThDP; 22 °C; 800 rpm…

View original post 386 more words

Pd/Cu-free Heck and Sonogashira cross-coupling reaction by Co nanoparticles immobilized on magnetic chitosan as reusable catalyst

 

Pd/Cu-free Heck and Sonogashira cross-coupling reaction by Co nanoparticles immobilized on magnetic chitosan as reusable catalyst

Green Chem., 2017, Advance Article
DOI: 10.1039/C6GC03377F, Paper
Abdol R. Hajipour, Fatemeh Rezaei, Zahra Khorsandi
Chitosan (CS) is a porous, self-standing, nanofibrillar microsphere that can be used as a metal carrier. Amino groups on CS enable to modulate cobalt coordination using a safe organic ligand (methyl salicylate).

Pd/Cu-free Heck and Sonogashira cross-coupling reaction by Co nanoparticles immobilized on magnetic chitosan as reusable catalyst

aDepartment of Chemistry, Isfahan University of Technology, Isfahan 84156, Iran
E-mail: haji@cc.iut.ac.ir
Fax: +98 311 391 2350
Tel: +98 311 391 3262
bDepartment of Neuroscience, University of Wisconsin, Medical School, Madison, USA
Green Chem., 2017, Advance Article

DOI: 10.1039/C6GC03377F

Department of Chemistry
Office : College of Chemistry, Isfahan University of Technology, Isfahan 84156, IR IranPhone : +98 311 391xxxxFax : +98 311 391xxxxWeb Site : Prof. Abdolreza Hajipour
EDUCATION:
1970-1974               High School, Shahpour high school, Kazerun, IR, Iran
1975-1979               B.S., Chemistry, Department of Chemistry, Isfahan University, Isfahan, I.R. Iran
1981-1983               M.S., Organic Chemistry, Synthesis, Shiraz University, Shiraz, I.R. Iran
Thesis Title: “Synthesis of 2,6,7,11-Tetraphenyl Isobenzofuran B Cyclobutadiene”
Advisor: Professor Habib Firouzabadi
1990-1994               Ph.D., Organic Chemistry, Wollongong University, Australia
Dissertation Title: “Asymmetric Synthesis of Chiral Amines and Benzazepine Alkaloids from Chiral Sulfoxides”
Advisor: Professor Stephen G. Pyne

POSITIONS:
09/94-11/98            Assistant Professor, Isfahan University of Technology
12/98-02/03            Associate Professor, Isfahan University of Technology
03/03-present        Professor, Isfahan University of Technology
02/01-03/02            Visiting Scientist, University of Wisconsin Medical School, Madison, WI
04/02-09/02            Associate Researcher, University of Wisconsin Medical School, Madison, WI
10/02-1/05              Associate Scientist, University of Wisconsin Medical School, Madison, WI
1/04 to present      Senior Scientist, University of Wisconsin Medical School, Madison, WI
 str1
Chitosan (CS) is a porous, self-standing, nanofibrillar microsphere that can be used as a metal carrier. Amino groups on CS enable to modulate cobalt coordination using a safe organic ligand (methyl salicylate). This catalyst efficiently promotes Heck cross-coupling of a large library of functional substrates under mild and sustainable conditions (polyethylene glycol as solvent at 80 °C in a short time (1 h)). The cobalt complex was also used as a heterogeneous, efficient, inexpensive, and green catalyst for Sonogashira cross-coupling reactions. The reactions of various aryl halides and phenylacetylene provided the corresponding products in moderate to good yields. More importantly, this phosphine, copper, and palladium-free catalyst was stable under the reaction conditions and could be easily reused using an external magnet for at least five successive runs without a discernible decrease in its catalytic activity.
Reaction yields were analyzed by gas chromatography (GC, BEIFEN-3420, detector type: FID, TCD equipped with Nukol™ capillary GC column, size × I.D. 30 m × 0.25 mm, df 0.25 μm). 2,3-Dimethylnaphthalene as was used as internal standard. The gas flow rate of 2 mL min-1; and oven temperature at 80 oC for 15 min and then increased to 170 oC.
str1
str2
General procedure for catalyst preparation The magnetic nanoparticles (MNPs) were prepared according to the method reported in literature64 based on the precipitation of magnetite nanoparticles from a mixture of iron(III) chloride and iron(II) sulfate by ammonia (25% solution in water). Subsequently, in a round-bottom flask equipped with a mechanical stirrer and condenser, a mixture of magnetic nanoparticles and sodium sulfate (20%, w/v) was added to a solution of chitosan (1%, w/v) in acetic acid (2%, w/v) under stirring. Stirring was continued for 1 h to obtain the aqueous suspension of MNPs/CS. Then, the magnetic nanoparticles were separated from the reaction mixture by an external permanent magnet, washed with ethanol and methanol several times, and dried under vacuum at 70 °C. For the preparation of supported methyl salicylate ligands, a solution of ethanol suspension of MNPs/CS (1.5 g per 10 mL) was added to methyl salicylate (6.5 mmol), and the mixture was stirred at 60 °C for 24 h. The final Co-MS@MNPs/CS was obtained as a brown solid by the addition of CoCl2·6H2O (4.2 mmol) dissolved in 10 mL of ethanol to disperse the mixture of MNPs/CS-MS (1.01 g) in ethanol (5 mL) and stirred at 60 °C for 18 h. The resulting complex was collected by an external permanent magnet, washed with ethanol (3 × 10 mL) to remove the unreacted materials, and finally dried in air (89% yield based on the amount of Co in the catalyst determined by ICP).
General procedure for the Heck reaction In a round-bottom flask equipped with a mechanical stirrer, a mixture of K3PO4 (4 eq.), olefin (1.1 mmol), and aryl halide (1 mmol) in PEG (3 mL) was added to 5 mg of catalyst (1.1 mol% of Co) and the flask was equipped with a condenser for refluxing. The abovementioned mixture was heated at 80 °C in an oil bath. The progress of the reaction was monitored by TLC (hexane/EtOAc, 80 : 20) and gas chromatography (GC). After the completion of the reaction, the mixture was diluted with dichloromethane and water. The organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatography. The products were characterized by comparing their physical properties, such as m.p., IR, 1 H, and 13C NMR spectra, with those reported in literature
General procedure for Sonogashira reaction In a round-bottom flask equipped with a mechanical stirrer, phenyl acetylene (1.2 mmol), aryl halide (1.0 mmol), catalyst (10 mg), and KOH (2 eq.) in DMSO (3 mL) were stirred under an air atmosphere at 140 °C. The progress of the reaction was monitored using TLC and GC. After the completion of the reaction, the mixture was diluted with dichloromethane and water. The organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. The product was isolated by column chromatography to afford the corresponding products in 55–80% yields. The products were characterized by comparing their physical properties, such as m.p, IR, 1 H, and 13C NMR spectra with those reported in literature.
////////////

Endogenous water-triggered and ultrasound accelerated synthesis of 1,5-disubstituted tetrazoles via a solvent and catalyst-free Ugi-azide reaction

 

Endogenous water-triggered and ultrasound accelerated synthesis of 1,5-disubstituted tetrazoles via a solvent and catalyst-free Ugi-azide reaction

Green Chem., 2017, Advance Article
DOI: 10.1039/C6GC03324E, Communication
Shrikant G. Pharande, Alma Rosa Corrales Escobosa, Rocio Gamez-Montano
An ultrasound accelerated, environmentally benign Ugi-azide based method was developed for the synthesis of 1,5-disubstituted tetrazoles under solvent and catalyst-free conditions.

Endogenous water-triggered and ultrasound accelerated synthesis of 1,5-disubstituted tetrazoles via a solvent and catalyst-free Ugi-azide reaction

 *Corresponding authors
aDepartamento de Química, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Noria Alta S/N, Col. Noria Alta, Guanajuato, México
E-mail: rociogm@ugto.mx
Green Chem., 2017, Advance Article

DOI: 10.1039/C6GC03324E,  http://pubs.rsc.org/en/Content/ArticleLanding/2017/GC/C6GC03324E?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

A novel, sustainable, endogenous water-triggered, environmentally friendly, high substrate scope, efficient, solvent-free and catalyst-free Ugi-azide based method for the synthesis of 1,5-disubstituted tetrazoles is described.
Shrikant Pharande

Shrikant Pharande

Doctoral student

Research experience

  • Apr 2014–Jun 2014, Research chemist
    TCG Lifesciences · pune
  • Mar 2012–Dec 2013, project assistant
    CSIR – National Chemical Laboratory, Pune · Organic Chemistry Division (NCL)
N-((1-(tert-butyl)-1H-tetrazol-5-yl)(4-chlorophenyl)methyl)aniline (4a)
Based on GP, 100 mg 4-Chlorobenzaldehyde (0.71 mmol), 0.065 cm3 aniline (0.71 mmol), 0.080 cm3 ter. Butyl isocyanide (0.71 mmol), and 0.093 cm3 TMS-azide (0.71 mmol) were reacted together to afford 237 mg (97%) as a white solid.
Melting range 144-145oC,
Rf = 0.45 (Hexane-AcOEt = 7/3 V/V),
1H NMR (500 MHz, CDCl3) δ 7.34 – 7.29 (m, 4H), 7.18 – 7.13 (m, 2H), 6.79 – 6.75 (m, 1H), 6.65 (d, J = 7.6 Hz, 2H), 6.11 (d, J = 6.2 Hz, 1H), 4.78 (d, J = 5.6 Hz, 1H), 1.71 (s, 9H);
13C NMR (126 MHz, CDCl3) δ 155.03, 145.54, 136.81, 134.71, 129.62, 129.43, 129.19, 119.64, 114.42, 61.95, 53.93, 30.29;
FT-IR (ATR) νmax/cm-1 3330.5, 3052.5, 2940.9, 1603.6, 1284.1;
HRMS (ESI+): m/z calcd. for C18H20ClN5 + 342.1480, found 342.1474
str1
str2

//////////////

FOTAGLIPTIN

New Drug Approvals

str1

SCHEMBL2020371.pngstr1

FOTAGLIPTIN

CAS 1312954-58-7

342.37, C17 H19 F N6 O

Benzonitrile, 2-[[3-[(3R)-3-amino-1-piperidinyl]-6-methyl-5-oxo-1,2,4-triazin-4(5H)-yl]methyl]-4-fluoro-

(R)-2-((3-(3-amino-piperidin-1-yl)-6-methyl-5-oxo-1,2,4-piperazine-4(5H)-yl)methyl)-4-fluorobenzonitrile,

BENZOATE 1403496-40-1

(R) 2- Methyl-5-oxo-1,2,4-triazin-4 (5H) -yl) methyl) -4-fluorobenzonitrile (3- benzoate (compound benzoate A), of the formula: the C . 17 the H 19 the FN . 6 O · the C . 7 the H . 6 O 2 , molecular weight: 464.49.

useful as a dipeptidyl peptidase IV (DPPIV) inhibitor for treating diabetes, particularly type 2 diabetes

Dipeptidyl peptidase IV inhibitor,

a DPPIV inhibitor, being developed by Chongqing Fochon, with licensee Shenzhen Salubris Pharmaceuticals, for treating type 2 diabetes mellitus. In January 2017, fotagliptin benzoate was reported to be in phase 1 clinical development. The compound of the present invention was first disclosed in WO2011079778. See WO2015110078 and WO2015110077, claiming crystalline polymorphic form of the DPPIV inhibitor.

  • Originator Chongqing Fochon Pharmaceutical
  • Class Antihyperglycaemics
  • Mechanism of Action CD26 antigen inhibitors
  • Shanghai Fosun Pharma…

View original post 3,583 more words

Towards automation of chemical process route selection based on data mining

Graphical abstract: Towards automation of chemical process route selection based on data mining

A methodology for chemical routes development and evaluation on the basis of data-mining is presented. A section of the Reaxys database was converted into a network, which was used to plan hypothetical synthesis routes to convert a bio-waste feedstock, limonene, to a bulk intermediate, benzoic acid. The route evaluation considered process conditions and used multiple indicators, including exergy, E-factor, solvent score, reaction reliability and route redox efficiency, in a multi-criteria environmental sustainability evaluation. The proposed methodology is the first route evaluation based on data mining, explicitly using reaction conditions, and is amenable to full automation.

In the field of process and synthetic chemistry ‘clean synthesis’ has become one of the standard criteria for good, commercially viable synthesis routes. As a result synthetic and process chemists must be equipped with adequate methodologies for quantification of ‘cleanness’ or ‘greenness’ of alternative routes at the early phases of the development cycle. These new criteria, and the traditional criteria of cost, security of supply, health and safety (H&S), and risk, provide a balanced picture of sustainability of a future technology. Thus, there are two separate aspects to process chemistry: developing the chemistry and the process, and evaluating the overall process, which must occur in parallel. Evaluation of the proposed routes requires data. As data science rapidly evolves, chemistry will inevitably use more of the new tools of data mining and data analysis to automate the routine tasks, such as evaluation of process metrics. In this paper we show some initial results in automation of process evaluation based on deep data mining of process chemistry and multi-criteria decision making.

The evaluation of greenness is a mature field, with a large number of published and standardised approaches, of which many are adopted by industry. 1 However, all published methods are highly case-specific and rather labour-intensive. In the field of synthetic routes development one of the most exciting new areas is the potential for automation of synthesis planning using data mining.2 What has never been attempted before is to automate route generation and evaluation in a coherent methodology, which would aid process development at the early, data-lean, stages. For this we show how to automatically generate process options using a network representation of a section of Reaxys database,3 followed by their screening using multi-criteria decision making, see Fig. 1. As the methods mature and become commercially available, such integration and automation will produce significant savings of time, and would deliver a far more detailed view of the competing synthesis route options than is generally possible at the early stages of design.

To date, obtaining the data, assembling the network and finding potential synthesis routes can already be carried out in a fully automated fashion. Due to issues around data availability the connection to the analysis of the routes still has to be initiated manually, involving a data curation step. The subsequent analysis and multi-criteria decision making have been largely automated in this study. To our knowledge this is the first example of the analysis of synthesis routes generated from the network representation of Reaxys obtained through datamining, using reaction conditions and process data.

image file: c6gc02482c-f2.tif

Fig. 2 A section of a network of organic chemistry. Dots are species and arrows represent reactions.
  1. D. J. C. Constable, C. Jimenez-Gonzalez and A. Lapkin, in Green Chemistry Metrics, John Wiley & Sons, Ltd, Chichester, UK, 2009, pp. 228–247 
  2. S. Szymkuć, E. P. Gajewska, T. Klucznik, K. Molga, P. Dittwald, M. Startek, M. Bajczyk and B. A. Grzybowski, Angew. Chem., Int. Ed., 2016, 55, 5904–5937 
  3. Reed Elsevier Properties SA, Login – Reaxys Login Page [Internet], 2014 [accessed 2014 Jun 8]. Available from: https://www.reaxys.com/. Reaxys is a trademark, copyright owned by Relex Intellectual properties SA and used under licence.

Towards automation of chemical process route selection based on data mining

*Corresponding authors
aDepartment of Chemical Engineering and Biotechnology, University of Cambridge, Cambridge CB2 3RA, UK
E-mail: aal35@cam.ac.uk
Green Chem., 2017,19, 140-152

DOI: 10.1039/C6GC02482C, http://pubs.rsc.org/en/Content/ArticleLanding/2017/GC/C6GC02482C?utm_medium=email&utm_campaign=pub-GC-vol-19-issue-1&utm_source=toc-alert#!divAbstract

Professor Alexei Lapkin, FRSC

Professor Alexei Lapkin FRSC

Professor of Sustainable Reaction Engineering

Fellow of Wolfson College

Catalytic Reaction Engineering

Sustainable Chemical Technologies

Office Phone: 330141

University of Cambridge
Image result for Department of Chemical Engineering and Biotechnology, University of Cambridge, Cambridge CB2 3RA, UK

Biography:

MChem in Biochemistry, Novosibirsk State University, 1994

PhD in Chemical Engineering, University of Bath, 2000

Boreskov Institute of Catalysis, Novosibirsk, Russia (1994-1997)

University of Bath, Department of Chemical Engineering, Research Officer (1997-2000)

University of Bath, Department of Chemical Engineering, Lecturer-SL-Reader (2000-2009)

University of Warwick, School of Engineering, Professor of Engineering (2009-2013)

Research Interests

Reaction Engineering group

Our group is developing cleaner manufacturing processes within chemical and chemistry using industries. We are mainly focusing on liquid- and multi-phase catalytic and biochemical processes. Within the group we have pursued projects on developing functional materials for catalysts, adsorbents and reactors, design of multi-functional intensive reactors, modelling of reaction kinetics and integrated processes, linking reaction kinetics with computational fluid dynamics (CFD) and linking process modelling with life cycle assessment (LCA), integration of reactions and separation.

Public funding:

The group is currently involved in an EU project ‘RECOBA’ (http://www.spire2030.eu/recoba/), in which our group collaborates with Materials and Electronic Engineering at Cambridge to work on innovative measurement techniques for monitoring processes under reaction conditions.

We are involved in the EPSRC project on developing novel routes to platform and functional molecules from waste terpenes, led by University of Bath.

We are involved in “Dial a Molecule 2” network funded by EPSRC.

Keywords

  • Reaction Engineering
  • flow
  • sustainability
  • heterogeneous catalysis
  • catalysis

Key Publications

J. Zakrzhewski, A.P. Smalley, M. Kabeshov, A. Lapkin, M. Gaunt, Continuous flow synthesis and derivatization of aziridines via palladium-catalyzed C(sp3)-H activation, Angew. Chem. Int. Ed., 55 (2016) 8878-8883.

P. Yaseneva, P. Hodgson, J. Zakrzewski, S. Falss, R.E. Meadows, A.A. Lapkin, Continuous flow Buchwald-Hartwig amination of a pharmaceutical intermediate, React. Chem. Eng., 1 (2016) 229-238.

P. Yaseneva, D. Plaza, X. Fan, K. Loponov, A. Lapkin, Synthesis of the antimalarial API artemether in a flow reactor, Catal. Today, 239 (2015) 90-96.

N. Peremezhney, E. Hines, A. Lapkin, C. Connaughton, Combining Gaussian processes, mutual information and a generic algorithm for multi-targeted optimisation of expensive-to-evaluate functions, Engineering Optimisation, 46 (2014) 1593-1607.

P. Yaseneva, C.F. Marti, E. Palomares, X. Fan, T. Morgan,P.S. Perez, M. Ronning, F. Huang,T. Yuranova, L. Kiwi-Minsker, S. Derrouiche, A.A. Lapkin, Efficient reduction of bromates using carbon nanofibre supported catalysts: experimental and a comparative life cycle assessment study, Chem. Eng. J., 248 (2014) 230-241

K.N. Loponov, J. Lopes, M. Barlog, E.V. Astrova, A.V. Malkov, A.A. Lapkin, Optimization of a Scalable Photochemical Reactor for Reactions with Singlet Oxygen, Org.Process Res.Dev., 18 (2014) 1443-1454.

X. Fan, V. Sans, P. Yaseneva, D. Plaza, J.M.J. Williams, A.A. Lapkin, Facile Stoichiometric Reductions in Flow: an Example of Artemisinin, Org.Process Res.Dev., 16 (2012) 1039-1042.

M.V. Sotenko, M. Rebros, V.S. Sans, K.N. Loponov, M.G. Davidson, G. Stephens, A.A. Lapkin, Tandem transformation of glycerol to esters, J. Biotechnol., 162 (2012) 390-397.

A.A. Lapkin, A. Voutchkova, P. Anastas, A conceptual framework for description of complexity in intensive chemical processes, Chem. Eng. Processing. Process intensification, 50 (2011) 1027-1034.

Lapkin, A., Peters, M., Greiner, L., Chemat, S., Leonhard, K., Liauw, M. A. and Leitner, W., Screening of new solvents for artemisinin extraction process using ab-initio methodology, Green Chem., 12 (2010) 241-251.

Lapkin, A. A. and Plucinski, P. K., Engineering factors for efficient flow processes in chemical industries, in Chemical reactions and processes under flow conditions, pp. 1- 43, Eds: Luis, S. V. and Garcia-Verdugo, E., Royal Society of Chemistry, Cambridge, 2010.

Iwan, A., Stephenson, H., Ketchie, W. C. and Lapkin, A. A., High temperature sequestration of CO2 using lithium zirconates, Chem. Eng. J., 146 (2009) 249-258.

Constable, D. J. C., Jimenez-Gonzalez, C. and Lapkin A., ‘Process metrics’, in Green chemistry metrics: measuring and monitoring sustainable processes, pp.  228- 247, Eds.: Lapkin, A. and Constable, D. J. C., Wiley-Blackwell, Chichester, 2008.

L.Torrente-Murciano, A.Lapkin, D.V. Bavykin, F.C. Walsh, K. Wilson, Highly selective Pd/titanate nanotubes catalysts for the double bond migration reaction, J. Catal., 245 (2007) 270-276.

A. Lapkin, P. Plucinski, Comparative assessment of technologies for extraction of artemisinin, J. Natural Prod., 69 (2006) 1653-1664.

D.V. Bavykin, A.A. Lapkin, S.T. Kolaczkowski, P.K. Plucinski, Selective oxidation of alcohols in a continuous multifunctional reactor: ruthenium oxide catalysed oxidation of benzyl alcohol, Applied Catal. A: General, 288 (2005) 165-174.

Image result for A. A. Lapkin

////////automation, chemical process,  route selection, data mining