Li, D;
Seavill, PW;
Wilden, JD;
(2019)
Application of Electrochemical Processes to Classical Iodocyclisation: Utility for Selectivity and Mechanistic Insight.
ChemElectroChem
, 6
(23)
pp. 5829-5835.
10.1002/celc.201901502.
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Abstract
The hazards and difficulties of handling elemental halogens such as I2 can be circumvented through the electrochemical generation of these species in situ and ‘on‐demand’. Advantages of this approach include the halogen being introduced into the reaction mixture at a steady rate, ensuring low concentrations to prevent halogenation of reactive aromatic rings. We also demonstrate that the Lewis acid required to promote this reaction, a Zn(II) salt, can also be generated in situ from a zinc‐coated graphite electrode in a clean and energy‐efficient manner. Mechanistic studies indicate an unusual pathway, which provides selectivity for the iodocyclisation without the often‐problematic electrophilic aromatic iodination of the aryl ring.
| Type: | Article |
|---|---|
| Title: | Application of Electrochemical Processes to Classical Iodocyclisation: Utility for Selectivity and Mechanistic Insight |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1002/celc.201901502 |
| Publisher version: | https://doi.org/10.1002/celc.201901502 |
| Language: | English |
| Additional information: | This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions. |
| Keywords: | electrochemistry, synthesis, mechanisms, processes, iodocyclisation |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices UCL > Provost and Vice Provost Offices > UCL BEAMS UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry |
| URI: | https://discovery.ucl.ac.uk/id/eprint/10085593 |
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