Synthesis of enantioenriched alkylfluorides by the fluorination of boronate complexes

Christopher Sandford; Ramesh Rasappan; Varinder K. Aggarwal

doi:10.1021/jacs.5b05848

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 journal › Article (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 language	English
Pages (from-to)	10100-10103
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	137
Issue number	32
Early online date	5 Aug 2015
DOIs	https://doi.org/10.1021/jacs.5b05848
Publication status	Published - 19 Aug 2015

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10.1021/jacs.5b05848

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2 Finished

3-month Core Capability for Chemistry Research
Crosby, J.
1/01/13 → 1/04/13
Project: Research
Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis
Aggarwal, V. K.
14/05/12 → 13/01/18
Project: Research

Professor Varinder K Aggarwal
- V.Aggarwal@bristol.ac.uk
- School of Chemistry - Alfred Capper Pass Chair of Chemistry
- Synthesis
- Supramolecular and Mechanistic Chemistry
- Catalysis
Person: Academic , Member

Cite this

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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.",

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AB - 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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Synthesis of enantioenriched alkylfluorides by the fluorination of boronate complexes

Abstract

Access to Document

3-month Core Capability for Chemistry Research

Changing the Synthesis Landscape with Boron at the Helm: from Chiral Organometallics to Assembly Line Synthesis

Professor Varinder K Aggarwal

Cite this