Premium
Anodic Olefin Coupling Reactions: Elucidating Radical Cation Mechanisms and the Interplay between Cyclization and Second Oxidation Steps
Author(s) -
Medcalf Zach,
Moeller Kevin D.
Publication year - 2021
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.202100118
Subject(s) - olefin fiber , chemistry , anode , anodic oxidation , radical ion , coupling reaction , reaction mechanism , redox , coupling (piping) , photochemistry , mechanism (biology) , combinatorial chemistry , catalysis , organic chemistry , materials science , electrode , ion , philosophy , epistemology , metallurgy
Anodic olefin coupling reactions generate new bonds and ring skeletons through a net two electron process that reverses the polarity of a known, electron‐rich functional group. While much of the early work on the mechanism of these reactions focused on the initial oxidation and cyclization steps of the process, the second oxidation step also plays a central role in determining the success of the reaction. Evidence supporting this observation is presented, along with evidence that optimization of this second oxidation step is not enough to pull a poor cyclization to the desired product. Successful cyclization reactions require optimization of both processes.