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Stereospecific Electrophilic Fluorination of Alkylcarbastannatrane Reagents
Author(s) -
Ma Xinghua,
Diane Mohamed,
Ralph Glenn,
Chen Christine,
Biscoe Mark R.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201704672
Subject(s) - nucleophile , stereospecificity , halogenation , chemistry , electrophile , electrophilic fluorination , reagent , fluoride , alkyl , catalysis , organic chemistry , combinatorial chemistry , medicinal chemistry , inorganic chemistry
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.