Synthesis of Enantioenriched Alkylfluorides by the Fluorination of Boronate Complexes | Zendy

Christopher Sandford | Zendy; Ramesh Rasappan | Zendy; Varinder K. Aggarwal | Zendy

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Synthesis of Enantioenriched Alkylfluorides by the Fluorination of Boronate Complexes

Author(s) -

Christopher Sandford,

Ramesh Rasappan,

Varinder K. Aggarwal

Publication year - 2015

Publication title -

journal of the american chemical society

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 7.115

H-Index - 612

eISSN - 1520-5126

pISSN - 0002-7863

DOI - 10.1021/jacs.5b05848

Subject(s) - chemistry , selectfluor , nucleophile , electrophile , alkyl , styrene , organic chemistry , electrophilic fluorination , boronic acid , combinatorial chemistry , reagent , catalysis , polymer , copolymer

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.

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