A general and atom-efficient continuous-flow approach to prepare amines, amides and imines via reactive N-chloramines

Katherine E. Jolley, Michael R. Chapman and A. John Blacker
Beilstein J. Org. Chem. 2018, 14, 2220–2228. https://doi.org/10.3762/bjoc.14.196

Supporting Information

Supporting Information File 1: Details of reactor assembly, NaOCl titration and NMR spectra.
Format: PDF Size: 2.2 MB Download

Cite the Following Article

A general and atom-efficient continuous-flow approach to prepare amines, amides and imines via reactive N-chloramines
Katherine E. Jolley, Michael R. Chapman and A. John Blacker
Beilstein J. Org. Chem. 2018, 14, 2220–2228. https://doi.org/10.3762/bjoc.14.196

How to Cite

Jolley, K. E.; Chapman, M. R.; Blacker, A. J. Beilstein J. Org. Chem. 2018, 14, 2220–2228. doi:10.3762/bjoc.14.196

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 155.1 KB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Constantinou, C. T.; Gkizis, P. L.; Lagopanagiotopoulou, O. T. G.; Skolia, E.; Nikitas, N. F.; Triandafillidi, I.; Kokotos, C. G. Photochemical Aminochlorination of Alkenes without the Use of an External Catalyst. Chemistry (Weinheim an der Bergstrasse, Germany) 2023, 29, e202301268. doi:10.1002/chem.202301268
  • Gaspa, S.; Sciortino, G.; Porcheddu, A.; Dell'Osa, C.; Satta, G.; Azzena, U.; Pisano, L.; Carraro, M.; Sanna, D.; Garribba, E.; Maseras, F.; De Luca, L. Oxidovanadium(IV) sulfate catalyses light-driven C–N bond formation. Molecular Catalysis 2023, 541, 113054. doi:10.1016/j.mcat.2023.113054
  • Polterauer, D.; Roberge, D. M.; Hanselmann, P.; Littich, R.; Hone, C. A.; Kappe, C. O. A continuous flow investigation of sulfonyl chloride synthesis using N-chloroamides: optimization, kinetics and mechanism. Reaction Chemistry & Engineering 2022, 7, 2582–2592. doi:10.1039/d2re00280a
  • Govada, G. V.; Sabbasani, R. R. A new outlook in oxidative transformations and coupling reactions via in situ generation of organic chloramines. Applied Organometallic Chemistry 2022, 36. doi:10.1002/aoc.6518
  • Li, B.; Yuan, J.; Ye, X.; Zhang, R.; Li, J.; Wang, Y.; Hu, J.; Dong, D. PIFA-Mediated Tandem Hofmann-Type Rearrangement and Cyclization Reaction of α-Acyl-β-aminoacrylamides: Access to Polysubstituted Oxazol-2(3H)-ones. The Journal of organic chemistry 2021, 86, 17944–17954. doi:10.1021/acs.joc.1c02276
  • Steiner, A.; de Frutos, O.; Rincón, J. A.; Mateos, C.; Williams, J. D.; Kappe, C. O. N-Chloroamines as substrates for metal-free photochemical atom-transfer radical addition reactions in continuous flow. Reaction Chemistry & Engineering 2021, 6, 2434–2441. doi:10.1039/d1re00429h
  • Morvan, J.; McBride, T.; Curbet, I.; Colombel‐Rouen, S.; Roisnel, T.; Crévisy, C.; Browne, D. L.; Mauduit, M. Continuous Flow Z‐Stereoselective Olefin Metathesis: Development and Applications in the Synthesis of Pheromones and Macrocyclic Odorant Molecules**. Angewandte Chemie 2021, 133, 19837–19842. doi:10.1002/ange.202106410
  • Morvan, J.; McBride, T.; Curbet, I.; Colombel-Rouen, S.; Roisnel, T.; Crévisy, C.; Browne, D. L.; Mauduit, M. Continuous Flow Z-Stereoselective Olefin Metathesis: Development and Applications in the Synthesis of Pheromones and Macrocyclic Odorant Molecules**. Angewandte Chemie (International ed. in English) 2021, 60, 19685–19690. doi:10.1002/anie.202106410
  • Engl, S.; Reiser, O. Catalyst-Free Visible-Light-Mediated Iodoamination of Olefins and Synthetic Applications. Organic letters 2021, 23, 5581–5586. doi:10.1021/acs.orglett.1c02035
  • Victoria, G. G.; Reddy, S. R. Recent advances in the synthesis of organic chloramines and their insights into health care. New Journal of Chemistry 2021, 45, 8386–8408. doi:10.1039/d1nj01086g
  • Taylor, C. J. Ph.D. Thesis, Dec 1, 2020.
  • Liao, J.; Zhang, S.; Wang, Z.; Song, X.; Zhang, D.; Kumar, R.; Jin, J.; Ren, P.; You, H.; Chen, F.-E. Transition-metal catalyzed asymmetric reactions under continuous flow from 2015 to early 2020. Green Synthesis and Catalysis 2020, 1, 121–133. doi:10.1016/j.gresc.2020.08.001
  • Danahy, K. E.; Styduhar, E. D.; Fodness, A. M.; Heckman, L. M.; Jamison, T. F. On-Demand Generation and Use in Continuous Synthesis of the Ambiphilic Nitrogen Source Chloramine. Organic letters 2020, 22, 8392–8395. doi:10.1021/acs.orglett.0c03021
  • Niño, C. G. Ph.D. Thesis, Aug 10, 2020.
  • Hafner, A.; Sedelmeier, J. Organometallic Chemistry in Industry; Wiley, 2020; pp 61–90. doi:10.1002/9783527819201.ch3
  • Wang, J.; Yi, W.-J. Practical N-Hydroxyphthalimide-Mediated Oxidation of Sulfonamides to N-Sulfonylimines. Molecules (Basel, Switzerland) 2019, 24, 3771. doi:10.3390/molecules24203771
Other Beilstein-Institut Open Science Activities