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The dual role of thiourea in the thiotrifluoromethylation of alkenes

Abstract:

Alkenes substituted with a thiourea undergo C-CF3 followed by intramolecular C-S bond formation with the Togni reagent and trifluoroacetic acid (TFA) at room temperature; thiols and thioamides are not suitable S-sources for this reaction. This anti-addition process involves a CF3 radical, and affords CF3-substituted thiazolines and thiazines for medicinal applications. A metal or photoredox catalyst is not required as the thiourea acts as a reductant, as well as serving as an S-source capable...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1039/c6sc02790c

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Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Role:
Author
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Institution:
University of Oxford
Division:
MPLS Division
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
ORCID:
0000-0002-8461-3909
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Funding agency for:
Ricci, P
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Funding agency for:
Pfeifer, L
Grant:
316882
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Funding agency for:
Gouverneur, V
Grant:
Wolfson Research Merit Award
Publisher:
Royal Society of Chemistry Publisher's website
Journal:
Chemical Science Journal website
Volume:
8
Issue:
2
Pages:
1195-1199
Publication date:
2016-09-30
Acceptance date:
2016-09-30
DOI:
EISSN:
2041-6539
ISSN:
2041-6520
Pmid:
28451260
Source identifiers:
679686
Language:
English
Keywords:
Pubs id:
pubs:679686
UUID:
uuid:4f1e7529-6415-4e8a-886a-a1637bda9e07
Local pid:
pubs:679686
Deposit date:
2018-10-17

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