Radical 1,4/5-Amino Shift Enables Access to Fluoroalkyl-Containing Primary β(γ)-Aminoketones under Metal-Free Conditions

Autor:	Bang-Yi Wei, Dian Wei, Jian-Wu Zhang, Tuming Liu, Ning Jiao, Yi-Heng He, Bing Han, Jiahao Pan
Rok vydání:	2021
Předmět:	chemistry.chemical_classification Primary (chemistry) Chemistry Alkene chemistry.chemical_element Sequence (biology) General Chemistry General Medicine Oxygen Catalysis chemistry.chemical_compound Reagent Polymer chemistry Dehydrogenation Bond cleavage Quinuclidine
Zdroj:	Angewandte Chemie (International ed. in English). 60(50)
ISSN:	1521-3773
Popis:	A novel radical 1,4/5-amino shift from the oxygen center of alkene-tethered diphenyl ketoxime ethers to the carbon center to achieve high value-added fluoroalkyl-containing primary β(γ)-amino-ketones is reported. Mechanism studies reveal that the migration is triggered by the alkene addition of fluoroalkyl radical derived from the electron donor-acceptor (EDA) complex of Togni's reagent II or fluoroalkyl iodides and quinuclidine, and involves a unique 5(6)-exo-trig cyclization of the carbon-centered radical onto the N-atom of ketoxime ethers followed by a cascade sequence of N-O bond cleavage and dehydrogenation. Notably, besides Togni's reagent II and fluoroalkyl iodides, this protocol is also compatible with other radical precursors to provide various functionalized primary aminoketones.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::83113ef69e854ea0c4df614595b5e77d https://pubmed.ncbi.nlm.nih.gov/34783428 Zobrazit plný text záznamu Plný text