Dr David Cantillo
Senior Lecturer
School of Chemistry and Molecular Biosciences
+61 7 336 53932
Chemistry Building (68), Room 626
Primary research interest
Organic chemistry – synthetic organic electrochemistry – flow chemistry
About me
After completing my undergraduate studies and obtaining my PhD in Organic Chemistry at the University of Extremadura, I joined the University of Graz in 2011 as a postdoctoral researcher (Prof Kappe). At the end of 2015, I joined the Research Center Pharmaceutical Engineering GmbH as a Senior Scientist. In 2018, I was appointed Scientific Area Head at the same institution and in parallel started my independent academic career at the University of Graz as an Assistant Professor. I joined the University of Queensland in 2023.
Research focus
Electrochemical synthetic method development
We research on novel methods for the synthesis of organic compounds based on the anodic oxidation and/or cathodic reduction of organic compounds. Electron exchange with an electrode surface can generate high energy intermediates such as radicals, carbocations and carbanions from relatively inert and simply organic compounds under mild conditions. Thus, electrochemistry can be used to enable reactions difficult to accomplish with conventional methods.
Sustainable electrochemical synthesis of pharmaceuticals
Electrochemical methods utilize electrical current instead of reagents to realize organic transformations, avoiding the use of stoichiometric amounts of chemicals and thus reducing costs and waste. We apply these principles to the development of new, greener electrochemistry-based routes for the synthesis of medicines.
Flow chemistry and flow electrolysis
This research focuses on the development of technologies for the scale-up of electrochemical reactions and other transformations
Teaching interests
Organic chemistry, electro-organic synthesis, sustainable chemistry
Achievements and awards
- Thieme Chemistry Journals Award (2020)
- Inventor award of the University of Graz (2017 and 2023)
- UNEX Extraordinary PhD Award (Sciences)
- Member of the Advisory Board – Chimica Oggi
- Member of the Scientific Advisory Board - Axplora
Patents
- C. O. Kappe, F. Sommer, D. Cantillo, Electrochemical reactor and processes using the electrochemical reactor, WO2023180283A2, Sep 9, 2023.
- G. Glotz, D. Cantillo, C. O. Kappe; Processes for preparing nor-opioid compounds and opioid antagonists by electrochemical N-demethylation, WO2021249708, Dec 1, 2021.
- C. O. Kappe, B. Gutmann, U. Weigl, P. Egli, D. P. Cox, D. Cantillo; Processes and oxazolidine-containing intermediates for the preparation of morphine analogs and derivatives, WO 2017/185004 Al, Oct 26, 2017.
- B. Wolf, R. Goetz, C. O. Kappe, D. Cantillo; Process for manufacturing 1,4-benzoxazinones, EP 3 184 515 A1, Jun 28, 2017.
Featured publications
M. Y. S. Ibrahim, G. R. Cumming, R. Gonzalez de Vega, P. Garcia-Losada, O. de Frutos, C. O. Kappe, D. Cantillo. Electrochemical Nickel-Catalyzed C(sp3)–C(sp3) Cross-Coupling of Alkyl Halides with Alkyl Tosylates. J. Amer. Chem. Soc 2023, 145, 17023-17028. DOI: 10.1021/jacs.3c07313.
F. Sommer, R. Gerber Aeschbacher, U. Thurnheer, C. O. Kappe, D. Cantillo. Sustainable Synthesis of Noroxymorphone via a Key Electrochemical N-Demethylation Step. ACS Sustain. Chem. Eng. 2022, 10, 8988-8996. DOI: 10.1021/acssuschemeng.2c02824.
M. Köckinger, P. Hanselmann, D. Roberge, P. Geotti-Bianchini, C. O. Kappe, D. Cantillo. Sustainable Electrochemical Decarboxylative Acetoxylation of Aminoacids in Batch and Continuous Flow. Green Chem. 2021, 23, 2382-2390. DOI: 10.1039/D1GC00201E.
Researcher biography
David Cantillo studied chemistry at the University of Extremadura, Spain. In 2011, he obtained his PhD under the supervision of Prof. Jose Luis Jimenez at the same university. His PhD work focused on the experimental and theoretical study of 1,3-dipolar cycloadditions of mesoionic compounds. Then, he moved to the University of Graz as a postdoctoral researcher within the group of Prof. C. Oliver Kappe, where he gained experience in flow chemistry. In 2018, he started his independent academic career at the University of Graz as an Assistant Professor and became an Area Leader at the Research Center Pharmaceutical Engineering GmbH. David has joined the University of Queensland in 2023.
His research group focuses on synthetic organic electrochemistry. In particular, the group explores the use of electrical current to develop novel synthetic methodologies and more sustainable routes for the synthesis of medicines, as well as process scale up using continuous flow technology.
Journal Articles
Rial-Rodríguez, Eduardo, Williams, Jason D., Cantillo, David, Fuchß, Thomas, Sommer, Alena, Eggenweiler, Hans-Michael, Kappe, C. Oliver and Laudadio, Gabriele (2024). An Automated Electrochemical Flow Platform to Accelerate Library Synthesis and Reaction Optimization. Angewandte Chemie. doi: 10.1002/ange.202412045
Welch, Bradley Graeme and Cantillo, David (2024). Merging Inline NMR Monitoring and Flow Chemistry in the Undergraduate Organic Chemistry Laboratory. Journal of Chemical Education, 101 (8), 3459-3465. doi: 10.1021/acs.jchemed.4c00429
Petrović, Nikola, Cumming, Graham R., Hone, Christopher A., Nieves-Remacha, María José, García-Losada, Pablo, de Frutos, Óscar, Kappe, C. Oliver and Cantillo, David (2024). Design of Experiments-Based Optimization of an Electrochemical Decarboxylative Alkylation Using a Spinning Cylinder Electrode Reactor. Organic Process Research & Development, 28 (7), 2928-2934. doi: 10.1021/acs.oprd.4c00178
Cantillo, David (2024). Recent advances in synthetic organic electrochemistry using flow systems. Current Opinion in Electrochemistry, 44 101459, 101459. doi: 10.1016/j.coelec.2024.101459
Malviya, Bhanwar K., Hansen, Eric C., Kong, Caleb J., Imbrogno, Joseph, Verghese, Jenson, Guinness, Steven M., Salazar, Chase A., Desrosiers, Jean-Nicolas, Kappe, C. Oliver and Cantillo, David (2024). Scalable Quasi-Divided Cell Operation Using Spinning Cylinder Electrode Technology: Multigram Electrochemical Synthesis of an Axitinib Intermediate. Organic Process Research & Development, 28 (3), 790-797. doi: 10.1021/acs.oprd.3c00508
Castillo-Garcia, Antonio A., Kappe, Christian Oliver, Cantillo, David and Barta, Katalin (2024). Aniline derivatives from lignin under mild conditions enabled by electrochemistry. ChemSusChem, 17 (3) e202301374. doi: 10.1002/cssc.202301374
Rial-Rodríguez, Eduardo, Williams, Jason D., Eggenweiler, Hans-Michael, Fuchss, Thomas, Sommer, Alena, Kappe, C. Oliver and Cantillo, David (2024). Development of an open-source flow-through cyclic voltammetry cell for real-time inline reaction analytics. Reaction Chemistry and Engineering, 9 (1), 26-30. doi: 10.1039/d3re00535f
Cantillo, David (2024). Electrochemical synthesis: A flourishing green technology for the manufacturing of organic compounds. Current Research in Green and Sustainable Chemistry 100416, 100416. doi: 10.1016/j.crgsc.2024.100416
Malviya, Bhanwar K., Laudadio, Gabriele, Kappe, C. Oliver and Cantillo, David (2024). Scalable catalyst free electrochemical chlorination of aminophenol derivatives enabled by a quasi-divided cell approach. Green Chemistry, 26 (20), 10479-10485. doi: 10.1039/d4gc03569k
Prieschl, Michael, Cantillo, David, Kappe, C. Oliver and Laudadio, Gabriele (2024). Scalable electrocatalyzed formation of C–O bonds using flow reactor technology. Reaction Chemistry & Engineering. doi: 10.1039/d4re00438h
Lunghi, Enrico, Ronco, Pietro, Della Negra, Federico, Trucchi, Beatrice, Verzini, Massimo, Merli, Daniele, Casali, Emanuele, Kappe, C Oliver, Cantillo, David and Zanoni, Giuseppe (2023). Electrifying Friedel-Crafts intramolecular alkylation toward 1,1-disubstituted tetrahydronaphthalenes. The Journal of Organic Chemistry, 88 (24), 16783-16789. doi: 10.1021/acs.joc.3c01281
Rial-Rodríguez, Eduardo, Wagner, Johannes F., Eggenweiler, Hans-Michael, Fuchss, Thomas, Sommer, Alena, Kappe, C. Oliver, Williams, Jason and Cantillo, David (2023). A Low-Volume Flow Electrochemical Microreactor for Rapid and Automated Process Optimization. Reaction Chemistry & Engineering, 9 (1), 1-6. doi: 10.1039/d3re00586k
Malviya, Bhanwar K., Bottecchia, Cecilia, Stone, Kevin, Lehnherr, Dan, Lévesque, François, Kappe, C. Oliver and Cantillo, David (2023). Multigram electrochemical Hofmann rearrangement using a spinning three-dimensional anode. Organic Process Research and Development, 27 (11), 2183-2191. doi: 10.1021/acs.oprd.3c00332
Malviya, Bhanwar K., Hansen, Eric C., Kong, Caleb J., Imbrogno, Joseph, Verghese, Jenson, Guinness, Steven M., Salazar, Chase A., Desrosiers, Jean‐Nicolas, Kappe, C. Oliver and Cantillo, David (2023). Metal‐free electrochemical reduction of disulfides in an undivided cell under mass transfer control. Chemistry: A European Journal, 29 (66) e202302664, 1-7. doi: 10.1002/chem.202302664
Petrović, Nikola, Malviya, Bhanwar K., Kappe, C. Oliver and Cantillo, David (2023). Scaling-up electroorganic synthesis using a spinning electrode electrochemical reactor in batch and flow mode. Organic Process Research and Development, 27 (11), 2072-2081. doi: 10.1021/acs.oprd.3c00255
Ibrahim, Malek Y. S., Cumming, Graham R., Gonzalez de Vega, Raquel, Garcia-Losada, Pablo, de Frutos, Oscar, Kappe, C. Oliver and Cantillo, David (2023). Electrochemical nickel-catalyzed C(sp3)–C(sp3) cross-coupling of alkyl halides with alkyl tosylates. Journal of the American Chemical Society, 145 (31), 17023-17028. doi: 10.1021/jacs.3c07313
Castillo, Ismael, Rehrl, Jakob, Sagmeister, Peter, Lebl, Rene, Kruisz, Julia, Celikovic, Selma, Sipek, Martin, Kirschneck, Dirk, Horn, Martin, Sacher, Stephan, Cantillo, David, Williams, Jason D., Khinast, Johannes G. and Kappe, Oliver (2023). Control of a complex multistep process for the production of mesalazine. Journal of Process Control, 122, 59-68. doi: 10.1016/j.jprocont.2022.12.009
Cantillo, David, Monedero, Martin, Dapremont, Olivier, Lusso, Carlo, McLaws, Mark, Blocher, Thomas, Wiles, Charlotte, Houldsworth, Stephen, Vizza, Alessandra, Hornung, Christian H., Kaaden, Anne, Stam, Wouter, McKay, Chris, Katz, Marianna, Borukhova, Svetlana, Kirschneck, Dirk, Ni, Xiong-Wei, Guillermin, Jean-Baptiste, Rouchet, Jean-Baptiste, Yazdanpanah, Nima, Roletto, Jacopo, Jenkins, Gareth, Poechlauer, Peter, Nuño, Manuel and Adamo, Andrea (2022). Panel discussion on... FLOW CHEMISTRY. Chimica Oggi, 40 (4), 16-41.
Sommer, Florian, Gerber Aeschbacher, Roman, Thurnheer, Urs, Kappe, C. Oliver and Cantillo, David (2022). Sustainable synthesis of noroxymorphone via a key electrochemical N-demethylation step. ACS Sustainable Chemistry and Engineering, 10 (27), 8988-8996. doi: 10.1021/acssuschemeng.2c02824
Jud, Wolfgang, Salazar, Chase A., Imbrogno, Joseph, Verghese, Jenson, Guinness, Steven M., Desrosiers, Jean-Nicolas, Kappe, C. Oliver and Cantillo, David (2022). Electrochemical oxidation of alcohols using nickel oxide hydroxide as heterogeneous electrocatalyst in batch and continuous flow. Organic Process Research and Development, 26 (5), 1486-1495. doi: 10.1021/acs.oprd.2c00064
Lebl, Rene, Zhu, Yutong, Ng, Derrick, Hornung, Christian H., Cantillo, David and Kappe, C. Oliver (2022). Scalable continuous flow hydrogenations using Pd/Al2O3-coated rectangular cross-section 3D-printed static mixers. Catalysis Today, 383, 55-63. doi: 10.1016/j.cattod.2020.07.046
Cantillo, David (2022). Synthesis of active pharmaceutical ingredients using electrochemical methods: keys to improve sustainability. Chemical Communications, 58 (5), 619-628. doi: 10.1039/d1cc06296d
Glotz, Gabriel, Waniek, Katharina, Schöggl, Josef-Peter, Cantillo, David, Stueckler, Clemens, Arzt, Anton, Gollner, Andreas, Schipfer, Rudolf, Baumgartner, Rupert J. and Kappe, C. Oliver (2021). Continuous flow synthesis of a blocked polyisocyanate: process intensification, reaction monitoring via in-line FTIR analysis, and comparative life cycle assessment. Organic Process Research and Development, 25 (10), 2367-2379. doi: 10.1021/acs.oprd.1c00329
Sommer, Florian, Cantillo, David and Kappe, C. Oliver (2021). A small footprint oxycodone generator based on continuous flow technology and real-time analytics. Journal of Flow Chemistry, 11 (4), 707-715. doi: 10.1007/s41981-021-00193-y
Jud, Wolfgang, Sommer, Florian, Kappe, C. Oliver and Cantillo, David (2021). Electrochemical α-arylation of ketones via anodic oxidation of in situ generated silyl enol ethers. The Journal of Organic Chemistry, 86 (22), 16026-16034. doi: 10.1021/acs.joc.1c01224
Jud, Wolfgang, Kappe, C. Oliver and Cantillo, David (2021). One-pot multistep electrochemical strategy for the modular synthesis of epoxides, glycols, and aldehydes from alkenes. Electrochemical Science Advances, 1 (3) e2100002, 1-9. doi: 10.1002/elsa.202100002
Cantillo, David, Sommer, Florian and Kappe, C. Oliver (2021). Chemoselective electrochemical oxidation of secondary alcohols using a recyclable chloride-based mediator. Synlett, 33 (02), 166-170. doi: 10.1055/a-1511-8869
Sagmeister, Peter, Lebl, Rene, Castillo, Ismael, Rehrl, Jakob, Kruisz, Julia, Sipek, Martin, Horn, Martin, Sacher, Stephan, Cantillo, David, Williams, Jason D. and Kappe, C. Oliver (2021). Advanced real-time process analytics for multistep synthesis in continuous flow. Angewandte Chemie-International Edition, 60 (15), 8139-8148. doi: 10.1002/anie.202016007
Musci, Pantaleo, von Keutz, Timo, Belaj, Ferdinand, Degennaro, Leonardo, Cantillo, David, Kappe, C. Oliver and Luisi, Renzo (2021). Flow technology for telescoped generation, lithiation and electrophilic (C3) functionalization of highly strained 1-azabicyclo[1.1.0]butanes. Angewandte Chemie-International Edition, 60 (12), 6395-6399. doi: 10.1002/anie.202014881
Sommer, Florian, Kappe, C. Oliver and Cantillo, David (2021). Electrochemically enabled one‐pot multistep synthesis of C19 androgen steroids. Chemistry: A European Journal, 27 (19), 6044-6049. doi: 10.1002/chem.202100446
Köckinger, Manuel, Hanselmann, Paul, Roberge, Dominique M., Geotti-Bianchini, Piero, Kappe, C. Oliver and Cantillo, David (2021). Sustainable electrochemical decarboxylative acetoxylation of aminoacids in batch and continuous flow. Green Chemistry, 23 (6), 2382-2390. doi: 10.1039/d1gc00201e
Prieschl, Michael, Cantillo, David and Kappe, C. Oliver (2020). A continuous flow bromodimethylsulfonium bromide generator: application to the synthesis of 2-arylaziridines from styrenes. Journal of Flow Chemistry, 11 (2), 117-125. doi: 10.1007/s41981-020-00125-2
Strauss, Franz J., Pöchlauer, Peter, Schuster, Christian, Kohls, Paul, Steinhofer, Stefan, Zinganell, Christopher, Gutmann, Bernhard, Cantillo, David and Kappe, C. Oliver (2020). Continuous on demand generation of acrolein from glycerol using a reactive distillation strategy. Chimica Oggi/Chemistry Today, 38 (6), 24-27.
Jud, Wolfgang, Kappe, C. Oliver and Cantillo, David (2020). Development and assembly of a flow cell for single‐pass continuous electroorganic synthesis using laser‐cut components. Chemistry–Methods, 1 (1), 36-41. doi: 10.1002/cmtd.202000042
von Keutz, Timo, Cantillo, David and Kappe, C. Oliver (2020). Organomagnesium based flash chemistry: continuous flow generation and utilization of halomethylmagnesium intermediates. Organic Letters, 22 (19), 7537-7541. doi: 10.1021/acs.orglett.0c02725
Glotz, Gabriel, Kappe, C. Oliver and Cantillo, David (2020). Electrochemical N-demethylation of 14-hydroxy morphinans: sustainable access to opioid antagonists. Organic Letters, 22 (17), 6891-6896. doi: 10.1021/acs.orglett.0c02424
Jud, Wolfgang, Kappe, C. Oliver and Cantillo, David (2020). A continuous flow cell for high‐temperature/high‐pressure electroorganic synthesis. ChemElectroChem, 7 (13), 2777-2783. doi: 10.1002/celc.202000696
Chen, Yuesu, Glotz, Gabriel, Cantillo, David and Kappe, C. Oliver (2020). Organophotocatalytic N‐demethylation of oxycodone using molecular oxygen. Chemistry: A European Journal, 26 (13), 2973-2979. doi: 10.1002/chem.201905505
Maljuric, Snjezana, Jud, Wolfgang, Kappe, C. Oliver and Cantillo, David (2020). Translating batch electrochemistry to single-pass continuous flow conditions: an organic chemist’s guide. Journal of Flow Chemistry, 10 (1), 181-190. doi: 10.1007/s41981-019-00050-z
von Keutz, Timo, Cantillo, David and Kappe, C. Oliver (2019). Continuous flow synthesis of terminal epoxides from ketones using in situ generated bromomethyl lithium. Organic Letters, 21 (24), 10094-10098. doi: 10.1021/acs.orglett.9b04072
Lebl, René, Murray, Trevor, Adamo, Andrea, Cantillo, David and Kappe, C. Oliver (2019). Continuous flow synthesis of methyl oximino acetoacetate: accessing greener purification methods with inline liquid–liquid extraction and membrane separation technology. ACS Sustainable Chemistry and Engineering, 7 (24), 20088-20096. doi: 10.1021/acssuschemeng.9b05954
Jud, Wolfgang, Maljuric, Snjezana, Kappe, C. Oliver and Cantillo, David (2019). Cathodic C–H trifluoromethylation of arenes and heteroarenes enabled by an in situ-generated triflyltriethylammonium complex. Organic Letters, 21 (19), 7970-7975. doi: 10.1021/acs.orglett.9b02948
Lebl, Rene, Cantillo, David and Kappe, C. Oliver (2019). Continuous generation, in-line quantification and utilization of nitrosyl chloride in photonitrosation reactions. Reaction Chemistry and Engineering, 4 (4), 738-746. doi: 10.1039/c8re00323h
Chen, Yuesu, Cantillo, David and Kappe, C. Oliver (2019). Visible light‐promoted Beckmann rearrangements: separating sequential photochemical and thermal phenomena in a continuous flow reactor. European Journal of Organic Chemistry, 2019 (11), 2163-2171. doi: 10.1002/ejoc.201900231
von Keutz, Timo, Cantillo, David and Kappe, C. Oliver (2019). Enhanced mixing of biphasic liquid-liquid systems for the synthesis of gem-dihalocyclopropanes using packed bed reactors. Journal of Flow Chemistry, 9 (1), 27-34. doi: 10.1007/s41981-018-0026-1
Aguiar, Renata M., Leão, Raquel A. C., Mata, Alejandro, Cantillo, David, Kappe, C. Oliver, Miranda, Leandro S. M. and de Souza, Rodrigo O. M. A. (2019). Continuous-flow protocol for the synthesis of enantiomerically pure intermediates of anti epilepsy and anti tuberculosis active pharmaceutical ingredients. Organic and Biomolecular Chemistry, 17 (6), 1552-1557. doi: 10.1039/c8ob03088j
Jud, Wolfgang, Kappe, C. Oliver and Cantillo, David (2019). On the reactivity of anodically generated trifluoromethyl radicals toward aryl alkynes in organic/aqueous media. Organic and Biomolecular Chemistry, 17 (14), 3529-3537. doi: 10.1039/c9ob00456d
Jud, Wolfgang, Kappe, C. Oliver and Cantillo, David (2018). Catalyst‐free oxytrifluoromethylation of alkenes through paired electrolysis in organic‐aqueous media. Chemistry: A European Journal, 24 (65), 17234-17238. doi: 10.1002/chem.201804708
Chen, Yuesu, de Frutos, Oscar, Mateos, Carlos, Rincon, Juan A., Cantillo, David and Kappe, C. Oliver (2018). Continuous flow photochemical benzylic bromination of a key intermediate in the synthesis of a 2-oxazolidinone. Chemphotochem, 2 (10), 906-912. doi: 10.1002/cptc.201800114
von Keutz, Timo, Strauss, Franz J., Cantillo, David and Kappe, C. Oliver (2018). Continuous flow multistep synthesis of α-functionalized esters via lithium enolate intermediates. Tetrahedron, 74 (25), 3113-3117. doi: 10.1016/j.tet.2017.11.063
Cantillo, David (2018). Review of Timothy Noël (ed): photochemical processes in continuous flow reactors: from engineering principles to chemical applications. Journal of Flow Chemistry, 8 (2), 107-108. doi: 10.1007/s41981-018-0011-8
Znidar, Desiree, Cantillo, David, Inglesby, Phillip, Boyd, Alistair and Kappe, C. Oliver (2018). Process intensification and integration studies for the generation of a key aminoimidazole intermediate in the synthesis of lanabecestat. Organic Process Research and Development, 22 (5), 633-640. doi: 10.1021/acs.oprd.8b00089
Rossa, Thais A., Suveges, Nicolas S., Sa, Marcus M., Cantillo, David and Kappe, C. Oliver (2018). Continuous multistep synthesis of 2-(azidomethyl)oxazoles. Beilstein Journal of Organic Chemistry, 14, 506-514. doi: 10.3762/bjoc.14.36
Mata, Alejandro, Cantillo, David and Kappe, C. Oliver (2017). An integrated continuous-flow synthesis of a key oxazolidine intermediate to noroxymorphone from naturally occurring opioids. European Journal of Organic Chemistry, 2017 (44), 6505-6510. doi: 10.1002/ejoc.201700811
Cantillo, David, Inglesby, Phillip A., Boyd, Alistair and Kappe, C. Oliver (2017). Hydrogen sulfide chemistry in continuous flow: Efficient synthesis of 2-oxopropanethioamide. Journal of Flow Chemistry, 7 (2), 29-32. doi: 10.1556/1846.2017.00006
Cantillo, David and Kappe, C. Oliver (2017). Halogenation of organic compounds using continuous flow and microreactor technology. Reaction Chemistry and Engineering, 2 (1), 7-19. doi: 10.1039/c6re00186f
Gutmann, Bernhard, Cantillo, David, Weigl, Ulrich, Cox, D. Phillip and Kappe, C. Oliver (2017). Design and development of Pd-catalyzed aerobic N-demethylation strategies for the synthesis of noroxymorphone in continuous flow mode. European Journal of Organic Chemistry, 2017 (4), 914-927. doi: 10.1002/ejoc.201601453
Cantillo, David, Wolf, Bernd, Goetz, Roland and Kappe, C. Oliver (2017). Continuous flow synthesis of a key 1,4-benzoxazinone intermediate via a nitration/hydrogenation/cyclization sequence. Organic Process Research and Development, 21 (1), 125-132. doi: 10.1021/acs.oprd.6b00409
Guerra, Javier, Cantillo, David and Kappe, C. Oliver (2016). Visible-light photoredox catalysis using a macromolecular ruthenium complex: reactivity and recovery by size-exclusion nanofiltration in continuous flow. Catalysis Science and Technology, 6 (13), 4695-4699. doi: 10.1039/c6cy00070c
Nikolaev, Valerij A., Cantillo, David, Kappe, C. Oliver, Medvedev, Jury J., Prakash, G. K. Surya and Supurgibekov, Murat B. (2016). Diazo strategy for the synthesis of pyridazines: pivotal impact of the configuration of the diazo precursor on the process. Chemistry: A European Journal, 22 (1), 174-184. doi: 10.1002/chem.201503448
Cantillo, David, Gutmann, Bernhard and Kappe, C. Oliver (2016). Safe generation and use of bromine azide under continuous flow conditions - selective 1,2-bromoazidation of olefins. Organic and Biomolecular Chemistry, 14 (3), 853-857. doi: 10.1039/c5ob02425k
Strauss, Franz J., Cantillo, David, Guerra, Javier and Kappe, C. Oliver (2016). A laboratory-scale continuous flow chlorine generator for organic synthesis. Reaction Chemistry and Engineering, 1 (5), 472-476. doi: 10.1039/c6re00135a
David Cantillo (2015). A pioneering early microreactor concept for ultrafast nitration reactions — Placing the seminal Brennecke and Kobe 1956 contribution into perspective. Journal of Flow Chemistry, 5 (4), 195-196. doi: 10.1556/1846.2015.00021
Cantillo, David, Mateos, Carlos, Rincon, Juan A., de Frutos, Oscar and Oliver Kappe, C. (2015). Light-induced C-H arylation of (hetero)arenes by in situ generated diazo anhydrides. Chemistry: A European Journal, 21 (37), 12894-12898. doi: 10.1002/chem.201502357
Cantillo, David and Kappe, C. Oliver (2015). Homogeneous vs immobilized palladium catalysts for continuous flow cross-coupling chemistry. Chimica Oggi, 33 (4), 6-10.
Gutmann, Bernhard, Cantillo, David and Kappe, C. Oliver (2015). Continuous-flow technology - A tool for the safe manufacturing of active pharmaceutical ingredients. Angewandte Chemie (International Edition), 54 (23), 6688-6728. doi: 10.1002/anie.201409318
Ullen, Andreas, Nusshold, Christoph, Glasnov, Toma, Saf, Robert, Cantillo, David, Eibinger, Gerald, Reicher, Helga, Fauler, Guenter, Bernhart, Eva, Hallstrom, Seth, Kogelnik, Nora, Zangger, Klaus, Kappe, C. Oliver, Malle, Ernst and Sattler, Wolfgang (2015). Covalent adduct formation between the plasmalogen-derived modification product 2-chlorohexadecanal and phloretin. Biochemical Pharmacology, 93 (4), 470-481. doi: 10.1016/j.bcp.2014.12.017
Greco, Roberto, Goessler, Walter, Cantillo, David and Kappe, C. Oliver (2015). Benchmarking immobilized Di- and triarylphosphine palladium catalysts for continuous-flow cross-coupling reactions: efficiency, durability, and metal leaching studies. ACS Catalysis, 5 (2), 1303-1312. doi: 10.1021/cs5020089
Cantillo, David and Kappe, C. Oliver (2014). Immobilized transition metals as catalysts for cross-couplings in continuous flow-a critical assessment of the reaction mechanism and metal leaching. ChemCatChem, 6 (12), 3286-3305. doi: 10.1002/cctc.201402483
Cantillo, David, Damm, Markus, Dallinger, Doris, Bauser, Marcus, Berger, Markus and Kappe, C. Oliver (2014). Sequential nitration/hydrogenation protocol for the synthesis of triaminophloroglucinol: safe generation and use of an explosive intermediate under continuous-flow conditions. Organic Process Research and Development, 18 (11), 1360-1366. doi: 10.1021/op5001435
Cantillo, David, de Frutos, Oscar, Rincon, Juan A., Mateos, Carlos and Kappe, C. Oliver (2014). A continuous-flow protocol for light-induced benzylic fluorinations. The Journal of Organic Chemistry, 79 (17), 8486-8490. doi: 10.1021/jo5016757
Cantillo, David, Avalos, Martin, Babiano, Reyes, Cintas, Pedro, Jimenez, Jose L., Light, Mark E., Palacios, Juan C. and Porro, Rocio (2014). Stepwise formation of 1,3-diazolium-4-thiolates by munchnone cycloadditions: promising candidates for nonlinear optics. The Journal of Organic Chemistry, 79 (9), 4201-4205. doi: 10.1021/jo500349g
Cantillo, David, de Frutos, Oscar, Rincon, Juan A., Mateos, Carlos and Kappe, C. Oliver (2014). Continuous flow α-trifluoromethylation of ketones by metal-free visible light photoredox catalysis. Organic Letters, 16 (3), 896-899. doi: 10.1021/ol403650y
Supurgibekov, Murat B., Cantillo, David, Kappe, C. Oliver, Prakash, G. K. Surya and Nikolaev, Valerij A. (2014). Effect of configuration of 2-vinyldiazocarbonyl compounds on their reactivity: experimental and computational study. Organic and Biomolecular Chemistry, 12 (4), 682-689. doi: 10.1039/c3ob42102c
Cantillo, David, de Frutos, Oscar, Rincon, Juan A., Mateos, Carlos and Kappe, C. Oliver (2014). A scalable procedure for light-induced benzylic brominations in continuous flow. The Journal of Organic Chemistry, 79 (1), 223-229. doi: 10.1021/jo402409k
Cantillo, David and Kappe, C. Oliver (2013). Direct preparation of nitriles from carboxylic acids in continuous flow. The Journal of Organic Chemistry, 78 (20), 10567-10571. doi: 10.1021/jo401945r
Pieber, Bartholomaeus, Martinez, Sabrina Teixeira, Cantillo, David and Kappe, C. Oliver (2013). In situ generation of diimide from hydrazine and oxygen: continuous-flow transfer hydrogenation of olefins. Angewandte Chemie (International Edition), 52 (39), 10241-10244. doi: 10.1002/anie.201303528
Cantillo, David, Moghaddam, Mojtaba Mirhosseini and Kappe, C. Oliver (2013). Hydrazine-mediated Reduction of Nitro and Azide Functionalities Catalyzed by Highly Active and Reusable Magnetic Iron Oxide Nanocrystals. Journal of Organic Chemistry, 78 (9), 4530-4542. doi: 10.1021/jo400556g
Gutmann, Bernhard, Gottsponer, Michael, Elsner, Petteri, Cantillo, David, Roberge, Dominique M. and Kappe, C. Oliver (2013). On the Fischer indole synthesis of 7-ethyltryptophol-mechanistic and process intensification studies under continuous flow conditions. Organic Process Research and Development, 17 (2), 294-302. doi: 10.1021/op300363s
Cantillo, David, Gutmann, Bernhard and Kappe, C. Oliver (2012). An experimental and computational assessment of acid-catalyzed azide-nitrile cycloadditions. The Journal of Organic Chemistry, 77 (23), 10882-10890. doi: 10.1021/jo3022742
Damm, Markus, Nusshold, Christoph, Cantillo, David, Rechberger, Gerald N., Gruber, Karl, Sattler, Wolfgang and Kappe, C. Oliver (2012). Can electromagnetic fields influence the structure and enzymatic digest of proteins? A critical evaluation of microwave-assisted proteomics protocols. Journal of Proteomics, 75 (18), 5533-5543. doi: 10.1016/j.jprot.2012.07.043
Cantillo, David, Avalos, Martin, Babiano, Reyes, Cintas, Pedro, Jimenez, Jose L. and Palacios, Juan C. (2012). On the prebiotic synthesis of D-sugars catalyzed by L-peptides: assessments from first-principles calculations. Chemistry: A European Journal, 18 (28), 8795-8799. doi: 10.1002/chem.201200466
Pieber, Bartholomaus, Cantillo, David and Kappe, C. Oliver (2012). Direct arylation of benzene with aryl bromides using high-temperature/high-pressure process windows: expanding the scope of C-H activation chemistry. Chemistry: A European Journal, 18 (16), 5047-5055. doi: 10.1002/chem.201103748
Cantillo, David, Sheibani, Hassan and Kappe, C. Oliver (2012). Flash flow pyrolysis: mimicking flash vacuum pyrolysis in a high-temperature/high-pressure liquid-phase microreactor environment. The Journal of Organic Chemistry, 77 (5), 2463-2473. doi: 10.1021/jo3001645
Dalla-Vechia, Luciana, Santos, Vanessa G., Godoi, Marla N., Cantillo, David, Kappe, C. Oliver, Eberlin, Marcos N., de Souza, Rodrigo O. M. A. and Miranda, Leandro S. M. (2012). On the mechanism of the Dakin-West reaction. Organic and Biomolecular Chemistry, 10 (45), 9013-9020. doi: 10.1039/c2ob26560e
Cantillo, David, Avalos, Martin, Babiano, Reyes, Cintas, Pedro, Jimenez, Jose L. and Palacios, Juan C. (2012). Fast and reliable location of stationary points in a reaction path. Journal of Physical Organic Chemistry, 25 (1), 77-82. doi: 10.1002/poc.1877
Cantillo, David, Baghbanzadeh, Mostafa and Kappe, C. Oliver (2012). In situ generated iron oxide nanocrystals as efficient and selective catalysts for the reduction of nitroarenes using a continuous flow method. Angewandte Chemie (International Edition), 51 (40), 10190-10193. doi: 10.1002/anie.201205792
Cantillo, David (2011). Mechanistic insights on the ruthenium-catalyzed hydrogenation of amides - C-N vs. C-O cleavage. European Journal of Inorganic Chemistry, 2011 (19), 3008-3013. doi: 10.1002/ejic.201100443
Cantillo, David, Gutmann, Bernhard and Kappe, C. Oliver (2011). Mechanistic insights on azide-nitrile cycloadditions: On the dialkyltin oxide-trimethylsilyl azide route and a new vilsmeier-haack-type organocatalyst. Journal of the American Chemical Society, 133 (12), 4465-4475. doi: 10.1021/ja109700b
Cantillo, David, Avalos, Martin, Babiano, Reyes, Cintas, Pedro, Jimenez, Jose L. and Palacios, Juan C. (2011). Assessing the whole range of CuAAC mechanisms by DFT calculations-on the intermediacy of copper acetylides. Organic and Biomolecular Chemistry, 9 (8), 2952-2958. doi: 10.1039/c0ob01001d
Cantillo, David, Avalos, Martin, Babiano, Reyes, Cintas, Pedro, Jimenez, Jose L. and Palacios, Juan C. (2011). On the enhanced reactivity and selectivity of triazole formation in molecular flasks. A theoretical rationale. Organic and Biomolecular Chemistry, 9 (22), 7638-7642. doi: 10.1039/c1ob06206a
Cantillo, David and Kappe, C. Oliver (2010). A unified mechanistic view on the Morita-Baylis-Hillman reaction: computational and experimental investigations. The Journal of Organic Chemistry, 75 (24), 8615-8626. doi: 10.1021/jo102094h
Cantillo, David, Avalos, Martin, Babiano, Reyes, Cintas, Pedro, Jimenez, Jose L., Light, Mark E. and Palacios, Juan C. (2010). Unusual aryl migration in a mesmeric betaine in the solid and liquid state: mechanistic insights into the SNAr reaction. The Journal of Organic Chemistry, 75 (12), 4300-4303. doi: 10.1021/jo100350t
Cantillo, David, Avalos, Martin, Babiano, Reyes, Cintas, Pedro, Jimenez, Jose L., Light, Mark E., Palacios, Juan C. and Rodriguez, Valentin (2010). Push-pull 1,3-thiazolium-5-thiolates. Formation via concerted and stepwise pathways, and theoretical evaluation of NLO properties. Organic and Biomolecular Chemistry, 8 (23), 5367-5374. doi: 10.1039/c0ob00416b
Cantillo, David, Avalos, Martin, Babiano, Reyes, Cintas, Pedro, Jimenez, Jose L., Light, Mark E. and Palacios, Juan C. (2009). Dissecting competitive mechanisms: thionation vs. cycloaddition in the reaction of thioisomunchnones with isothiocyanates under microwave irradiation. The Journal of Organic Chemistry, 74 (20), 7644-7650. doi: 10.1021/jo900960a
Cantillo, David, Avalos, Martin, Babiano, Reyes, Cintas, Pedro, Jimenez, Jose L., Light, Mark E. and Palacios, Juan C. (2009). Thionation of mesoionics with isothiocyanates: evidence supporting a four-step domino process and ruling out a [2+2] mechanism. The Journal of Organic Chemistry, 74 (10), 3698-3705. doi: 10.1021/jo900028c
Cantillo, David, Avalos, Martin, Babiano, Reyes, Cintas, Pedro, Jimenez, Jose L., Light, Mark E. and Palacios, Juan C. (2008). Stepwise cycloadditions of mesoionic systems: thionation of thioisomunchnones by isothlocyanates. Organic Letters, 10 (6), 1079-1082. doi: 10.1021/ol702929k
Conference Papers
Cantillo, David, Wolf, Bernd, Goetz, Roland and Kappe, C. (2017). Continuous flow synthesis of 1,4-benzoxazinones via a fully integrated nitration/hydrogenation/cyclization sequence. 254th National Meeting and Exposition of the American-Chemical-Society (ACS) on Chemistry's Impact on the Global Economy, Washington, DC United States, 20-24 August 2017. Washington, DC United States: American Chemical Society.
Kappe, C. Oliver and Cantillo, David (2014). α-Trifluoromethylation of ketones by metal-free visible light photoredox catalysis: Batch and continuous flow strategies. 248th National Meeting of the American-Chemical-Society (ACS), San Francisco, CA United States, 10-14 August 2014. Washington, DC United States: American Chemical Society.
Kappe, C. Oliver, Cantillo, David and Gutmann, Bernhard (2013). In search for an efficient catalyst for azide-nitrile cycloadditions: The synthesis of 5-substituted-1H-tetrazoles under batch and continuous flow conditions. 245th National Spring Meeting of the American-Chemical-Society (ACS), New Orleans, LA United States, 7-11 April 2013. Washington, DC United States: American Chemical Society.
Kappe, C. Oliver, Cantillo, David, Baghbanzadeh, Mostafa and Moghaddam, Mojtaba Mirhosseini (2013). In situ generated iron oxide nanocrystals as efficient and selective catalysts for the reduction of nitroarenes in batch and continuous flow formats. 245th National Spring Meeting of the American-Chemical-Society (ACS), New Orleans, LA United States, 7-11 April 2013. Washington, DC United States: American Chemical Society.
Kappe, C. Oliver, Cantillo, David and Gutmann, Bernhard (2011). Safe and scalable synthesis of 5-aryl-1H-tetrazoles in batch and continuous flow mode. 242nd National Meeting of the American-Chemical-Society (ACS), Denver, CO United States, 28 August - 1 September 2011. Washington, DC United States: American Chemical Society.
Patents
Kappe, Oliver, Sommer, Florian and Cantillo, David (2023). Electrochemical reactor and processes using the electrochemical reactor. WO2023180283A2.
Wolf, Bernd, Goetz, Roland, Kappe, C. Oliver and Cantillo, David (2017). Process for manufacturing 1,4-benzoxazinones. EP3184515A1.