David Cantillo

Summary

Affiliation: University of Extremadura
Country: Spain

Publications

  1. doi request reprint Stepwise cycloadditions of mesoionic systems: thionation of thioisomünchnones by isothiocyanates
    David Cantillo
    Departamento de Quimica Organica e Inorganica, QUOREX Research Group, Facultad de Ciencias, Universidad de Extremadura, Badajoz, Spain
    Org Lett 10:1079-82. 2008
  2. doi request reprint A unified mechanistic view on the Morita-Baylis-Hillman reaction: computational and experimental investigations
    David Cantillo
    Christian Doppler Laboratory for Microwave Chemistry CDLMC and Institute of Chemistry, Karl Franzens University Graz, Heinrichstrasse 28, A 8010 Graz, Austria
    J Org Chem 75:8615-26. 2010
  3. doi request reprint Unusual aryl migration in a mesomeric betaine in the solid and liquid state: mechanistic insights into the SNAr reaction
    David Cantillo
    Departamento de Quimica Organica e Inorganica, QUOREX Research Group, Facultad de Ciencias UEX, Avda de Elvas s n E 06071 Badajoz, Spain
    J Org Chem 75:4300-3. 2010
  4. doi request reprint On the prebiotic synthesis of D-sugars catalyzed by L-peptides: assessments from first-principles calculations
    David Cantillo
    Department of Organic and Inorganic Chemistry, University of Extremadura, Avda de Elvas s n, 06006 Badajoz, Spain
    Chemistry 18:8795-9. 2012
  5. doi request reprint Push-pull 1,3-thiazolium-5-thiolates. Formation via concerted and stepwise pathways, and theoretical evaluation of NLO properties
    David Cantillo
    Departamento de Quimica Organica e Inorganica, QUOREX Research Group, Facultad de Ciencias, Universidad de Extremadura, E 06006, Badajoz, Spain
    Org Biomol Chem 8:5367-74. 2010
  6. doi request reprint Dissecting competitive mechanisms: thionation vs. cycloaddition in the reaction of thioisomunchnones with isothiocyanates under microwave irradiation
    David Cantillo
    Departamento de Quimica Organica e Inorganica, QUOREX Research Group, Facultad de Ciencias, Universidad de Extremadura, E 06071 Badajoz, Spain
    J Org Chem 74:7644-50. 2009
  7. doi request reprint Assessing the whole range of CuAAC mechanisms by DFT calculations--on the intermediacy of copper acetylides
    David Cantillo
    Departamento de Quimica Organica e Inorganica, QUOREX Research Group, Facultad de Ciencias, Universidad de Extremadura, E 06006, Badajoz, Spain
    Org Biomol Chem 9:2952-8. 2011
  8. doi request reprint On the enhanced reactivity and selectivity of triazole formation in molecular flasks. A theoretical rationale
    David Cantillo
    Departamento de Quimica Organica e Inorganica, QUOREX Research Group, Facultad de Ciencias, Universidad de Extremadura, E 06006 Badajoz, Spain
    Org Biomol Chem 9:7638-42. 2011
  9. doi request reprint Thionation of mesoionics with isothiocyanates: evidence supporting a four-step domino process and ruling out a [2 + 2] mechanism
    David Cantillo
    Departamento de Quimica Organica e Inorganica, QUOREX Research Group, Facultad de Ciencias, Universidad de Extremadura, E 06071 Badajoz, Spain
    J Org Chem 74:3698-705. 2009
  10. doi request reprint Continuous flow α-trifluoromethylation of ketones by metal-free visible light photoredox catalysis
    David Cantillo
    Institute of Chemistry, University of Graz, Heinrichstrasse 28, A 8010 Graz, Austria
    Org Lett 16:896-9. 2014

Collaborators

Detail Information

Publications22

  1. doi request reprint Stepwise cycloadditions of mesoionic systems: thionation of thioisomünchnones by isothiocyanates
    David Cantillo
    Departamento de Quimica Organica e Inorganica, QUOREX Research Group, Facultad de Ciencias, Universidad de Extremadura, Badajoz, Spain
    Org Lett 10:1079-82. 2008
    ..The mechanistic pathway of such a transformation most likely involves a stepwise 1,3-dipolar cycloaddition, which is supported by theoretical calculations performed with a two-layer hybrid method (B3LYP/6-31G(d):PM3)...
  2. doi request reprint A unified mechanistic view on the Morita-Baylis-Hillman reaction: computational and experimental investigations
    David Cantillo
    Christian Doppler Laboratory for Microwave Chemistry CDLMC and Institute of Chemistry, Karl Franzens University Graz, Heinrichstrasse 28, A 8010 Graz, Austria
    J Org Chem 75:8615-26. 2010
    ..Depending on the specific reaction conditions both suggested pathways are competing mechanisms, and depending on the amount of protic species and the reaction progress (early or late stage) either of the two mechanisms will be favored...
  3. doi request reprint Unusual aryl migration in a mesomeric betaine in the solid and liquid state: mechanistic insights into the SNAr reaction
    David Cantillo
    Departamento de Quimica Organica e Inorganica, QUOREX Research Group, Facultad de Ciencias UEX, Avda de Elvas s n E 06071 Badajoz, Spain
    J Org Chem 75:4300-3. 2010
    ..The process changes drastically the optical and spectroscopic properties and should be a valuable model for related heteroaromatic systems...
  4. doi request reprint On the prebiotic synthesis of D-sugars catalyzed by L-peptides: assessments from first-principles calculations
    David Cantillo
    Department of Organic and Inorganic Chemistry, University of Extremadura, Avda de Elvas s n, 06006 Badajoz, Spain
    Chemistry 18:8795-9. 2012
    ....
  5. doi request reprint Push-pull 1,3-thiazolium-5-thiolates. Formation via concerted and stepwise pathways, and theoretical evaluation of NLO properties
    David Cantillo
    Departamento de Quimica Organica e Inorganica, QUOREX Research Group, Facultad de Ciencias, Universidad de Extremadura, E 06006, Badajoz, Spain
    Org Biomol Chem 8:5367-74. 2010
    ....
  6. doi request reprint Dissecting competitive mechanisms: thionation vs. cycloaddition in the reaction of thioisomunchnones with isothiocyanates under microwave irradiation
    David Cantillo
    Departamento de Quimica Organica e Inorganica, QUOREX Research Group, Facultad de Ciencias, Universidad de Extremadura, E 06071 Badajoz, Spain
    J Org Chem 74:7644-50. 2009
    ..The protocol is quite simple and should convince many organic chemists that certain daunting theoretical treatments can be made easy...
  7. doi request reprint Assessing the whole range of CuAAC mechanisms by DFT calculations--on the intermediacy of copper acetylides
    David Cantillo
    Departamento de Quimica Organica e Inorganica, QUOREX Research Group, Facultad de Ciencias, Universidad de Extremadura, E 06006, Badajoz, Spain
    Org Biomol Chem 9:2952-8. 2011
    ..The total proton/deuterium exchange in the afforded triazole demonstrates the formation of a copper acetylide intermediate during the transformation...
  8. doi request reprint On the enhanced reactivity and selectivity of triazole formation in molecular flasks. A theoretical rationale
    David Cantillo
    Departamento de Quimica Organica e Inorganica, QUOREX Research Group, Facultad de Ciencias, Universidad de Extremadura, E 06006 Badajoz, Spain
    Org Biomol Chem 9:7638-42. 2011
    ....
  9. doi request reprint Thionation of mesoionics with isothiocyanates: evidence supporting a four-step domino process and ruling out a [2 + 2] mechanism
    David Cantillo
    Departamento de Quimica Organica e Inorganica, QUOREX Research Group, Facultad de Ciencias, Universidad de Extremadura, E 06071 Badajoz, Spain
    J Org Chem 74:3698-705. 2009
    ..The mechanistic hypothesis has further been corroborated by an experiment with isotopically (13)C-labeled PhNCS that unambiguously shows the way in which the exchange reaction occurs...
  10. doi request reprint Continuous flow α-trifluoromethylation of ketones by metal-free visible light photoredox catalysis
    David Cantillo
    Institute of Chemistry, University of Graz, Heinrichstrasse 28, A 8010 Graz, Austria
    Org Lett 16:896-9. 2014
    ..The continuous protocol uses Eosin Y as an inexpensive photoredox catalyst and requires only 20 min to complete the two reaction steps. ..
  11. ncbi request reprint Stepwise Formation of 1,3-Diazolium-4-thiolates by Münchnone Cycloadditions: Promising Candidates for Nonlinear Optics
    David Cantillo
    Departamento de Quimica Organica e Inorganica, QUOREX Research Group, Facultad de Ciencias, Universidad de Extremadura, E 06006, Badajoz, Spain
    J Org Chem 79:4201-5. 2014
    ..Given the pattern substitution around the mesoionic ring resulting in a push-pull system, theoretical estimations predict large hyperpolarizabilities in some cases, which is typical of molecules exhibiting nonlinear optical responses. ..
  12. doi request reprint A continuous-flow protocol for light-induced benzylic fluorinations
    David Cantillo
    Institute of Chemistry, University of Graz, Heinrichstrasse 28, A 8010 Graz, Austria
    J Org Chem 79:8486-90. 2014
    ..Good to excellent isolated yields were obtained for a variety of substrates bearing different functional groups applying residence times below 30 min. ..
  13. doi request reprint Mechanistic insights on azide-nitrile cycloadditions: on the dialkyltin oxide-trimethylsilyl azide route and a new Vilsmeier-Haack-type organocatalyst
    David Cantillo
    Christian Doppler Laboratory for Microwave Chemistry CDLMC and Institute of Chemistry, Karl Franzens University Graz, Heinrichstrasse 28, A 8010 Graz, Austria
    J Am Chem Soc 133:4465-75. 2011
    ..As compared to the dialkylltin oxide-trimethylsilyl azide method, the organocatalytic system presented herein has the advantage of higher reactivity, in situ generation from inexpensive materials, and low toxicity...
  14. pmc Can electromagnetic fields influence the structure and enzymatic digest of proteins? A critical evaluation of microwave-assisted proteomics protocols
    Markus Damm
    Christian Doppler Laboratory for Microwave Chemistry CDLMC and Institute of Chemistry, Karl Franzens University Graz, Heinrichstrasse 28 I, A 8010 Graz, Austria
    J Proteomics 75:5533-43. 2012
    ..These simulations revealed that the applied field in a typical laboratory microwave reactor is 3-4 orders of magnitude too low to induce conformational changes in proteins or enzymes...
  15. doi request reprint An experimental and computational assessment of acid-catalyzed azide-nitrile cycloadditions
    David Cantillo
    Christian Doppler Laboratory for Microwave Chemistry and Institute of Chemistry, Karl Franzens University Graz, Heinrichstrasse 28, A 8010 Graz, Austria
    J Org Chem 77:10882-90. 2012
    ..The efficiency of this catalyst has been examined by preparation of a series of 5-substituted-1H-tetrazoles. The desired tetrazole structures were obtained in high yields within 3-10 min employing controlled microwave heating...
  16. doi request reprint Flash flow pyrolysis: mimicking flash vacuum pyrolysis in a high-temperature/high-pressure liquid-phase microreactor environment
    David Cantillo
    Christian Doppler Laboratory for Microwave Chemistry and Institute of Chemistry, Karl Franzens University Graz, Heinrichstrasse 28, A 8010 Graz, Austria
    J Org Chem 77:2463-73. 2012
    ..A correlation between computed activation energies and experimental gas-phase FVP (molecule-wall collisions) and liquid-phase FFP (molecule-molecule collisions) pyrolysis temperatures was derived...
  17. doi request reprint A scalable procedure for light-induced benzylic brominations in continuous flow
    David Cantillo
    Institute of Chemistry, University of Graz, Heinrichstrasse 28, A 8010 Graz, Austria
    J Org Chem 79:223-9. 2014
    ..For the bromination of phenylacetone as a model, a productivity of 180 mmol h(-1) for the desired bromide was achieved. ..
  18. doi request reprint Direct preparation of nitriles from carboxylic acids in continuous flow
    David Cantillo
    Institute of Chemistry, University of Graz, Heinrichstrasse 28, A 8010 Graz, Austria
    J Org Chem 78:10567-71. 2013
    ..The protocol has been tested for a variety of nitriles, including aromatic and aliphatic substrates. ..
  19. doi request reprint Hydrazine-mediated reduction of nitro and azide functionalities catalyzed by highly active and reusable magnetic iron oxide nanocrystals
    David Cantillo
    Christian Doppler Laboratory for Microwave Chemistry CDLMC and Institute of Chemistry, Karl Franzens University Graz, Heinrichstrasse 28, A 8010 Graz, Austria
    J Org Chem 78:4530-42. 2013
    ..Selected examples of anilines of industrial importance have been prepared in a continuous regime using this protocol...
  20. ncbi request reprint In Situ Generated Iron Oxide Nanocrystals as Efficient and Selective Catalysts for the Reduction of Nitroarenes using a Continuous Flow Method
    David Cantillo
    Christian Doppler Laboratory for Microwave Chemistry CDLMC and Institute of Chemistry, Karl Franzens University Graz, Heinrichstrasse 28, 8010 Graz Austria http www maos net
    Angew Chem Int Ed Engl 51:10190-3. 2012
    ..After completion of the reaction, the nanoparticles aggregate and can be recovered by a magnet...
  21. ncbi request reprint Direct arylation of benzene with aryl bromides using high-temperature/high-pressure process windows: expanding the scope of C-H activation chemistry
    Bartholomäus Pieber
    Christian Doppler Laboratory for Microwave Chemistry CDLMC and Institute of Chemistry, Karl Franzens University Graz, Heinrichstrasse 28, 8010 Graz, Austria
    Chemistry 18:5047-55. 2012
    ..In addition to metal-based catalysts, high-T/p process windows were also successfully applied to transition-metal-free systems, utilizing 1,10-phenanthroline as organocatalyst...
  22. doi request reprint Safe generation and use of bromine azide under continuous flow conditions--selective 1,2-bromoazidation of olefins
    David Cantillo
    Institute of Chemistry, University of Graz, NAWI Graz, Heinrichstrasse 28, A 8010 Graz, Austria
    Org Biomol Chem 14:853-7. 2016
    ..The resulting addition products have been used for the preparation of several useful building blocks. ..