title: Synthesis of Enantioenriched Alkylfluorides by the Fluorination of Boronate Complexes.
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.
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, United Kingdom.
authors.forename: Christopher
authors.initials: C
authors.lastname: Sandford
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, United Kingdom.
authors.forename: Ramesh
authors.initials: R
authors.lastname: Rasappan
authors.affiliation: School of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, United Kingdom.
authors.forename: Varinder K
authors.initials: VK
authors.lastname: Aggarwal
mesh_terms: D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D003979:Diazonium Compounds / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D005459:Fluorides / Q000737:chemistry*; D054879:Halogenation; D013237:Stereoisomerism; D020058:Styrene / Q000737:chemistry; D013696:Temperature
chemical_list: D001896:Boron Compounds; D001897:Boronic Acids; D003979:Diazonium Compounds; D004952:Esters; D020058:Styrene; C408750:selectfluor; D005459:Fluorides