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Controlled single and double iodofluorination of alkynes with DIH- and HF-based reagents

Abstract:
A novel protocol for the regio- and stereoselective iodofluorination of internal and terminal alkynes using 1,3-diiodo-5,5,-dimethylhydantoin and HF-based reagents is disclosed. This approach is used to prepare a fluorinated tamoxifen derivative in two steps from commercially available starting materials. A facile method enabling controlled regioselective double iodofluorination of terminal alkynes is also presented.
Publication status:
Published
Peer review status:
Peer reviewed
Version:
Accepted Manuscript

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Publisher copy:
10.1021/acs.orglett.8b00321

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Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
ORCID:
0000-0002-8461-3909
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Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Subgroup:
Organic Chemistry
Oxford college:
Merton College
ORCID:
0000-0001-8638-5308
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Funding agency for:
Pfeifer, L
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Funding agency for:
Gouverneur, V
Publisher:
American Chemical Society Publisher's website
Journal:
Organic Letters Journal website
Volume:
20
Issue:
6
Pages:
1576–1579
Publication date:
2018-03-01
Acceptance date:
2018-02-14
DOI:
EISSN:
1523-7052
ISSN:
1523-7060
Pubs id:
pubs:828632
URN:
uri:7e709092-3c7a-4c89-a854-636c3e2df48a
UUID:
uuid:7e709092-3c7a-4c89-a854-636c3e2df48a
Local pid:
pubs:828632
Language:
English

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