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Hydrogen bonding phase-transfer catalysis with Potassium Fluoride: enantioselective synthesis of β-fluoroamines

Abstract:

Potassium fluoride (KF) is an ideal reagent for fluorination because it is safe, easy to handle and low-cost. However, poor solubility in organic solvents coupled with limited strategies to control its reactivity has discouraged its use for asymmetric C-F bond formation. Here, we demonstrate that hydrogen bonding phase-transfer catalysis with KF provides access to valuable β-fluoroamines in high yields and enantioselectivities. This methodology employs a chiral N-ethyl bis-urea catalyst that ...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1021/jacs.8b12568

Authors


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Role:
Author
ORCID:
0000-0003-3084-3888
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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
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Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
ORCID:
0000-0002-2739-4156
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Sub department:
Inorganic Chemistry
Role:
Author
ORCID:
0000-0003-1683-2066
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Publisher:
American Chemical Society Publisher's website
Journal:
Journal of the American Chemical Society Journal website
Volume:
141
Issue:
7
Pages:
2878-2883
Publication date:
2019-01-28
Acceptance date:
2019-01-28
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
Pmid:
30689372
Source identifiers:
969006
Language:
English
Pubs id:
pubs:969006
UUID:
uuid:ca83b822-2e5d-4612-9c72-16580c155d92
Local pid:
pubs:969006
Deposit date:
2019-03-01

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