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Research published in the Journal of the American Chemical Society (JACS)

24 August 2015

Synthesis of Enantioenriched Alkylfluorides by the Fluorination of Boronate Complexes

Congratulations to Professor Varinder Aggarwal and co-authors Ramesh Rassapan and Christopher Sandford, who's research paper 'Synthesis of Enantioenriched Alkylfluorides by the Fluorination of Boronate Complexes' has been published in the Journal of the American Chemical Society (JACS).
 

The paper describes a new stereospecific method for converting chiral seconadry alkyl boronic esters into seconadry alkyl fluorides. 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.

 

 

Further information

Synthesis of Enantioenriched Alkylfluorides by the Fluorination of Boronate Complexes

Christopher Sandford, Ramesh Rasappan, and Varinder K. Aggarwal*
School of Chemistry, University of Bristol, Cantock’s Close, Bristol BS8 1TS, United Kingdom
J. Am. Chem. Soc., 2015, 137 (32), pp 10100–10103
DOI: 10.1021/jacs.5b05848
Publication Date (Web): August 5, 2015

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