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A Triazole‐Substituted Aryl Iodide with Omnipotent Reactivity in Enantioselective Oxidations
Author(s) -
Abazid Ayham H.,
Nachtsheim Boris J.
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201912023
Subject(s) - enantioselective synthesis , reactivity (psychology) , substituent , iodide , chemistry , aryl , selectivity , combinatorial chemistry , triazole , catalysis , organic chemistry , medicine , alkyl , alternative medicine , pathology
A widely applicable triazole‐substituted chiral aryl iodide is described as catalyst for enantioselective oxidation reactions. The introduction of a substituent in ortho‐position to the iodide is key for its high reactivity and selectivity. Besides a robust and modular synthesis, the main advantage of this catalyst is the excellent performance in a plethora of mechanistically diverse enantioselective transformations, such as spirocyclizations, phenol dearomatizations, α‐oxygenations, and oxidative rearrangements. DFT‐calculations of in situ generated [hydroxy(tosyloxy)iodo]arene isomers give an initial rational for the observed reactivity.