Application of Electrochemical Processes to Classical Iodocyclisation: Utility for Selectivity and Mechanistic Insight
Citations Over Time
Abstract
Abstract The hazards and difficulties of handling elemental halogens such as I 2 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.
Related Papers
- → LiCl-Accelerated Multimetallic Cross-Coupling of Aryl Chlorides with Aryl Triflates(2019)216 cited
- → Exotic Electrophiles in Chlorinated and Chloraminated Water: When Conventional Kinetic Models and Reaction Pathways Fall Short(2020)54 cited
- → Rh-Catalyzed Reactions of 1,4-Benzoquinones with Electrophiles: C–H Iodination, Bromination, and Phenylselenation(2016)60 cited
- → Perspective Chapter: Electrophiles and Lewis Acids(2023)1 cited
- → Halogen exchange reactions of perhalo-3-azaalkenes and their subsequent dehalogenation to form hetero-1,3-dienes(1991)5 cited