Chai Hongli, Zhen Xiang, Wang Xueqing, Qi Liang, Qin Yuji, Xue Jijun, Xu Zhaoqing, Zhang Hongrui, Zhu Weiwei
Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Science, Lanzhou University, Lanzhou 730000, China.
Department of Pharmacy, College of Life Sciences, China Jiliang University, Hangzhou 310018, China.
ACS Omega. 2022 Jun 1;7(23):19988-19996. doi: 10.1021/acsomega.2c01791. eCollection 2022 Jun 14.
Hypervalent iodine catalyst-catalyzed nucleophilic fluorination of unsaturated amides using BF·EtO 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.
报道了使用BF·EtO作为氟源和活化试剂,在高价碘催化剂催化下不饱和酰胺的亲核氟化反应。在10分钟内以良好至优异的产率(高达95%的分离产率)合成了各种5-氟-2-恶唑啉衍生物。该过程在温和条件下高效且无金属。基于先前的工作和实验结果,提出了一种涉及氟化/1,2-芳基迁移/环化级联的机理。