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Application of Electrochemical Processes to Classical Iodocyclisation: Utility for Selectivity and Mechanistic Insight
Author(s) -
Li Diyuan,
Seavill Peter W.,
Wilden Jonathan D.
Publication year - 2019
Publication title -
chemelectrochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.182
H-Index - 59
ISSN - 2196-0216
DOI - 10.1002/celc.201901502
Subject(s) - halogenation , electrophile , selectivity , halogen , electrochemistry , chemistry , lewis acids and bases , graphite , combinatorial chemistry , ring (chemistry) , aryl , zinc , organic chemistry , electrode , catalysis , alkyl
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.