期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 41, 页码 12663-12667出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201704672
关键词
carbastannatrane; fluorination; halogenation; Selectfluor; stereospecificity
资金
- National Institutes of Health [1SC1GM110010]
- Alfred P. Sloan Foundation
- PSC-CUNY
- National Science Foundation [CHE-0840498]
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.
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