A Triazole‐Substituted Aryl Iodide with Omnipotent Reactivity in Enantioselective Oxidations. (12th December 2019)

• Record Type: Journal Article
• Authors: Abazid, Ayham H.; Nachtsheim, Boris J.
• Is Part Of: Angewandte Chemie. Volume 132:Number 4(2020)
• Page Start: 1495
• Page End: 1500
• Publication Date: 2019-12-12
• Subjects: Asymmetrische Oxidation -- Chirale hypervalente Iodverbindungen -- Organokatalyse -- Oxidation -- Stereoselektive Synthese; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201912023
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: 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. Abstract : Der Alleskönner : Ein einfach synthetisierbares chirales Triazol‐substituiertes Aryliodid stellt einen vielseitigen Katalysator für eine Vielzahl Iod‐vermittelter enantioselektiver Oxidationen dar. Es übertrifft alle bislang bekannten chiralen hypervalenten Iod‐Vorläufer.