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Synthesis and applications of highly functionalized 1-halo-3-substituted bicyclo[1.1.1]pentanes

Abstract:

Bicyclo[1.1.1]pentanes (BCPs) are important bioisosteres of 1,4-disubstituted arenes, tert-butyl and acetylenic groups that can impart physicochemical benefits on drug candidates. Here we describe the synthesis of BCPs bearing carbon and halogen substituents under exceptionally mild reaction conditions, via triethylborane-initiated atom-transfer radical addition ring-opening of tricyclo[1.1.1.01,3]pentane (TCP) with alkyl halides. This chemistry displays broad substrate scope and functional g...

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Publication status:
Published
Peer review status:
Peer reviewed
Version:
Publisher's version

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Publisher copy:
10.1039/C8SC01355A

Authors


More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
ORCID:
0000-0002-5821-1965
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
ORCID:
0000-0002-3513-8267
More by this author
Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry; Organic Chemistry
Mousseau, JJ More by this author
Stepan, AF More by this author
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Publisher:
Royal Society of Chemistry Publisher's website
Journal:
Chemical Science Journal website
Volume:
9
Issue:
23
Pages:
5295-5300
Publication date:
2018-05-21
Acceptance date:
2018-05-20
DOI:
EISSN:
2041-6539
ISSN:
2041-6520
Pubs id:
pubs:858456
URN:
uri:22098225-945d-4121-9683-5c44f6df7334
UUID:
uuid:22098225-945d-4121-9683-5c44f6df7334
Local pid:
pubs:858456

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