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A Triazole-Substituted Aryl Iodide with Omnipotent Reactivity in Enantioselective Oxidations.

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.

SUBMITTER: Abazid AH

PROVIDER: S-EPMC7003988 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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A Triazole-Substituted Aryl Iodide with Omnipotent Reactivity in Enantioselective Oxidations.

Abazid Ayham H AH Nachtsheim Boris J BJ

Angewandte Chemie (International ed. in English) 20191212 4

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 oxidati ...[more]

PMID: 31600009

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