Direct Synthesis of 4‑Fluoroisoxazoles through Gold-Catalyzed Cascade Cyclization–Fluorination of 2‑Alkynone O‑Methyl Oximes

A tandem protocol for the synthesis of fluorinated isoxazoles has been developed via catalytic intramolecular cyclizations of 2-alkynone O-methyl oximes and ensuing fluorination. The reactions proceed smoothly at room temperature in the presence of 5 mol % of (IPr)AuCl, 5 mol % of AgOTs, 2.5 equiv o...

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Bibliographic Details
Published in:Journal of organic chemistry 2014-07, Vol.79 (14), p.6444-6455
Main Authors: Jeong, Yunkyung, Kim, Bom-I, Lee, Jae Kyun, Ryu, Jae-Sang
Format: Article
Language:English
Subjects:
Catalysis
Cyclization
Hydrocarbons, Fluorinated - chemical synthesis
Hydrocarbons, Fluorinated - chemistry
Isoxazoles - chemical synthesis
Isoxazoles - chemistry
Molecular Structure
Organogold Compounds - chemistry
Oximes - chemistry
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Summary:A tandem protocol for the synthesis of fluorinated isoxazoles has been developed via catalytic intramolecular cyclizations of 2-alkynone O-methyl oximes and ensuing fluorination. The reactions proceed smoothly at room temperature in the presence of 5 mol % of (IPr)AuCl, 5 mol % of AgOTs, 2.5 equiv of Selectfluor, and 2 equiv of NaHCO3. This process features an efficient one-pot cascade route to fluoroisoxazoles with high yields and high selectivity under mild reaction conditions.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo5008702