Synthesis of enantioenriched alkylfluorides by the fluorination of boronate complexes

Christopher Sandford, Ramesh Rasappan, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

43 Citations (Scopus)
310 Downloads (Pure)

Abstract

The enantiospecific conversion of chiral secondary boronic esters into alkylfluorides is reported. Boronate complexes derived from boronic esters and PhLi were used as nucleophiles, with Selectfluor II as the electrophilic fluorinating agent, to afford alkylfluorides in short reaction times. The addition of styrene as a radical trap was found to enhance enantiospecificity. A broad range of alkyl boronic esters were converted into alkylfluorides with almost complete enantiospecificity by this method.

Original languageEnglish
Pages (from-to)10100-10103
Number of pages4
JournalJournal of the American Chemical Society
Volume137
Issue number32
Early online date5 Aug 2015
DOIs
Publication statusPublished - 19 Aug 2015

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