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Stereospecific Electrophilic Fluorination of Alkylcarbastannatrane Reagents.

ABSTRACT: 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.

SUBMITTER: Ma X

PROVIDER: S-EPMC8054978 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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Stereospecific Electrophilic Fluorination of Alkylcarbastannatrane Reagents.

Ma Xinghua X Diane Mohamed M Ralph Glenn G Chen Christine C Biscoe Mark R MR

Angewandte Chemie (International ed. in English) 20170904 41

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 enan ...[more]

PMID: 28833888

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