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A Strategic Synthesis of Fluoroethers via Ring-Opening Fluorinative Beckmann Fragmentation
Chae Yeon Lee1, Su Eun Lee1, Hee Nam Lim1
1Department of Chemistry, Yeungnam University, 280 Daehak-Ro, Gyeongsan, Gyeongbuk 38541, Republic of Korea.
Abstract:
An SN1-type fluorination method for monofluoroethers is developed. The key to this reaction is fluorinative C-C bond cleavage that is driven by oxygen-assisted Beckmann fragmentation. To enable this transformation, cyclic α-aryloxyoximes derived from 3-coumaranone and 1-indanones were investigated as substrates, using N,N-diethylaminosulfur trifluoride (DAST) as a dual-role reagent of an oxime activator and fluoride donor. This method features the synthesis of an underdeveloped chemical motif with simple and mild operating conditions.
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