Journal
ACS OMEGA
Volume 7, Issue 23, Pages 19988-19996Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acsomega.2c01791
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Funding
- National Natural Science Foundation of China [91853106]
- Program for Guangdong Introducing Innovative and Enterpreneurial Teams [2016ZT06Y337]
- Guangdong Provincial Key Laboratory of Construction Foundation [2019B030301005]
- Shenzhen Science and Technology Program [JSGG20200225153121723]
- Fundamental Research Funds for the Central Universities [19ykzd25]
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In this study, a hypervalent iodine catalyst was utilized for the nucleophilic fluorination of unsaturated amides, using BF3·Et2O as the fluorine source and activating reagent. Various 5-fluoro-2-oxazoline derivatives were synthesized with good to excellent yields (up to 95% isolated yield) within a short time of 10 minutes. The process was efficient, metal-free, and conducted under mild conditions. A proposed mechanism involving fluorination/1,2-aryl migration/cyclization cascade was based on previous studies and experimental results.
Hypervalent iodine catalyst-catalyzed nucleophilic fluorination of unsaturated amides using BF3 center dot Et2O as the fluorine source and activating reagent was reported. Various 5-fluoro-2-oxazoline derivatives were synthesized in good to excellent yields (up to 95% isolated yield) within 10 min. The process was efficient and metal-free under mild conditions. A mechanism involving a fluorination/1,2-aryl migration/cyclization cascade was proposed on the basis of previous work and experimental results.
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