59456-20-1Relevant articles and documents
Enhancing the leaving group ability of alkyl fluorides: I/F exchange reactions mediated by LiI
Zerban, Jensen J.,Bagnall, Brody,Davis, Todd A.
supporting information, (2022/01/28)
The carbon–fluorine (C–F) bond is one of the strongest bonds in organic chemistry and generally inert toward nucleophilic substitution reactions. To overcome the relative inertness of the C–F bond, this work focused on the ability of simple lithium salts
One-Pot Deoxygenation and Substitution of Alcohols Mediated by Sulfuryl Fluoride
Epifanov, Maxim,Mo, Jia Yi,Dubois, Rudy,Yu, Hao,Sammis, Glenn M.
supporting information, p. 3768 - 3777 (2021/03/01)
Sulfuryl fluoride is a valuable reagent for the one-pot activation and derivatization of aliphatic alcohols, but the highly reactive alkyl fluorosulfate intermediates limit both the types of reactions that can be accessed as well as the scope. Herein, we report the SO2F2-mediated alcohol substitution and deoxygenation method that relies on the conversion of fluorosulfates to alkyl halide intermediates. This strategy allows the expansion of SO2F2-mediated one-pot processes to include radical reactions, where the alkyl halides can also be exploited in the one-pot deoxygenation of primary alcohols under mild conditions (52-95% yield). This strategy can also enhance the scope of substitutions to nucleophiles that are previously incompatible with one-pot SO2F2-mediated alcohol activation and enables substitution of primary and secondary alcohols in 54-95% yield. Chiral secondary alcohols undergo a highly stereospecific (90-98% ee) double nucleophilic displacement with an overall retention of configuration.
Stereospecific Electrophilic Fluorination of Alkylcarbastannatrane Reagents
Ma, Xinghua,Diane, Mohamed,Ralph, Glenn,Chen, Christine,Biscoe, Mark R.
supporting information, p. 12663 - 12667 (2017/09/11)
We report the use of isolable primary and secondary alkylcarbastannatrane nucleophiles in site-specific fluorination reactions. These reactions occur without the need for transition metal catalysis or in situ activation of the nucleophile. In the absence of the carbastannatrane backbone, alkyltin nucleophiles exhibit no activity towards fluorination. When enantioenriched alkylcarbastannatranes are employed, fluorination occurs predominately via a stereoinvertive mechanism to generate highly enantioenriched alkyl fluoride compounds. These conditions can also be extended to stereospecific chlorination, bromination, and iodination reactions.