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Organoselenium-Catalyzed Oxidative Allylic Fluorination with Electrophilic N–F Reagent
ACS Catalysis ( IF 12.9 ) Pub Date : 2018-01-05 00:00:00 , DOI: 10.1021/acscatal.7b03829
Ruizhi Guo 1 , Jiachen Huang 1 , Xiaodan Zhao 1
Affiliation  

An efficient route of organoselenium-catalyzed oxidative allylic fluorination has been developed. In this transformation, bulky electrophilic fluorinating reagent N-fluoro-2,4,6-trimethylpyridinium triflate (TMFP-OTf) was employed as the oxidant and fluorine source. Notably, TEMPO as an additive affects the fluorination and leads to better substrate scope and excellent functional group tolerance. By this protocol, a variety of allylic fluorides were synthesized in good to excellent yields. The obtained allylic fluorides could be converted into vinyl fluorides efficiently in the presence of an appropriate base.

中文翻译:

亲电子NF试剂催化有机硒催化氧化烯丙基氟化

已经开发出有机硒催化的氧化烯丙基氟化的有效途径。在该转化中,使用大体积的亲电氟化试剂三氟甲磺酸N-氟-2,4,6-三甲基吡啶鎓(TMFP-OTf)作为氧化剂和氟源。值得注意的是,TEMPO作为添加剂会影响氟化作用,并导致更好的基材范围和出色的官能团耐受性。通过该方案,合成了多种烯丙基氟化物,收率良好至极佳。在适当的碱的存在下,可以将获得的烯丙基氟化物有效地转化为氟乙烯。
更新日期:2018-01-05
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