Journal
ACS CATALYSIS
Volume 8, Issue 2, Pages 926-930Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b03829
Keywords
selenium catalysis; alkene; electrophilic fluorinating reagents; fluorination; allylic reaction
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Funding
- Sun Yat-Sen University
- One Thousand Youth Talents Program of China
- Natural Science Foundation of Guangdong Province [2014A030312018]
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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.
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