2038-62-2Relevant articles and documents
PREPARATION OF MONOFLUOROCARBOXYLIC ACIDS USING N,N-DIETHYL-1,1,2,3,3,3-HEXAFLUOROPROPYLAMINE
O'Hagan, D.
, p. 371 - 378 (1989)
A method is outlined for the preparation of monofluorocarboxylic acids using Ishikawa's reagent, (C2H5)2NCF2CHFCF3 (PPDA), directly from hydroxyesters, or indirectly from monofluorinated alkylbenzenes, followed by the oxidation of the phenyl ring to a carboxylic acid.The chiral fluorocarboxylic acids, (2S) and (2R)-3-fluoro-2-methylpropionates (>99percent ee) and (2S)-2-fluoropropionic acid (55percent ee) are prepared as are 3-fluoropropionate and 4-fluorobutyrate.
SUBSTITUENT CONSTANTS FOR ALIPHATIC FUNCTIONS OBTAINED FROM PARTITION
IWASA,FUJITA,HANSCH
, p. 150 - 153 (1965)
-
A facile conversion of primary or secondary alcohols with n-perfluorobutane-sulfonyl fluoride/1,8-diazabicyclo[5.4.0]undec-7-ene into their corresponding fluorides
Bennua-Skalmowski
, p. 2611 - 2614 (1995)
The combination of n-perfluorobutanesulfonyl fluoride (2) with 1,8-diazabicyclo-[5.4.0]undec-7-ene efficiently converts primary and secondary alcohols in unipolar solvents into their corresponding fluorides.
Efficient protocol for the SO2F2-mediated deoxyfluorination of aliphatic alcohols
Epifanov, Maxim,Lai, Joey,Lee, Cayo,Sammis, Glenn M.,Wang, Cindy Xinyun
supporting information, (2021/09/28)
Alkyl fluorides are prevalent in both the pharmaceutical and agrochemical industries. As such, there has been significant interest over the past 40 years in the development of new synthetic methods to access these important fluorinated motifs. Herein we report the sulfuryl fluoride-mediated deoxyfluorination of alcohols using room temperature reaction conditions in only an hour. A wide range of primary aliphatic alcohols were efficiently converted to the corresponding fluoride in 46-70% isolated yields. Secondary alcohols were also effectively deoxyfluorinated in 50–92% yields. Chiral secondary alcohols were cleanly converted to the corresponding alkyl fluoride with only a minor deterioration of the enantioenrichment. A steroid derivative also underwent deoxyfluorination in 50% yield and 5.9:1 dr, with the major product resulting from net inversion of the stereocenter.
A Series of Deoxyfluorination Reagents Featuring OCF2Functional Groups
Cao, Wei,Chen, Qing-Yun,Guo, Yong,Su, Zhaoben,Wu, Chengying,Zhao, Shiyu
supporting information, (2020/11/03)
Research on perfluoroalkyl ether carboxylic acids (PFECAs) as alternatives for perfluoroalkyl substances continues with the goal of protecting the environment. However, very little is known about the utilization of decomposition products of PFECAs. We report herein a new series of deoxyfluorination reagents featuring OCF2 functional groups derived from certain PFECAs. Alkyl fluorides were generated from various alcohols in ≤97% yield by these novel reagents. The mechanistic experiment verified in situ generation of carbonic difluoride (COF2).