Open Access
Catalytic hydrotrifluoromethylation of styrenes and unactivated aliphatic alkenes via an organic photoredox system
Publication type: Journal Article
Publication date: 2013-05-21
scimago Q1
wos Q1
SJR: 2.138
CiteScore: 12.6
Impact factor: 7.4
ISSN: 20416520, 20416539
General Chemistry
Abstract
Herein is presented a direct method for the metal-free hydrotrifluoromethylation of alkenes. The method relies on the single electron oxidation of a commercially available sodium trifluoromethanesulfinate salt (CF3SO2Na, Langlois reagent) by N-Me-9-mesityl acridinium as a photoredox catalyst. Methyl thiosalicylate is used as a substoichiometric H-atom donor for aliphatic alkenes, and thiophenol is used as a stoichiometric H-atom donor for styrenyl substrates. The substrate scope for the transformation is broad, including mono-, di- and trisubstituted aliphatic and styrenyl alkenes, with high regioselectivity in nearly all cases examined.
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Metrics
418
Total citations:
418
Citations from 2025:
12
(2.87%)
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GOST
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Wilger D. J., Gesmundo N. J., Nicewicz D. A. Catalytic hydrotrifluoromethylation of styrenes and unactivated aliphatic alkenes via an organic photoredox system // Chemical Science. 2013. Vol. 4. No. 8. p. 3160.
GOST all authors (up to 50)
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Wilger D. J., Gesmundo N. J., Nicewicz D. A. Catalytic hydrotrifluoromethylation of styrenes and unactivated aliphatic alkenes via an organic photoredox system // Chemical Science. 2013. Vol. 4. No. 8. p. 3160.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1039/c3sc51209f
UR - https://doi.org/10.1039/c3sc51209f
TI - Catalytic hydrotrifluoromethylation of styrenes and unactivated aliphatic alkenes via an organic photoredox system
T2 - Chemical Science
AU - Wilger, Dale J.
AU - Gesmundo, Nathan J
AU - Nicewicz, David A
PY - 2013
DA - 2013/05/21
PB - Royal Society of Chemistry (RSC)
SP - 3160
IS - 8
VL - 4
SN - 2041-6520
SN - 2041-6539
ER -
Cite this
BibTex (up to 50 authors)
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@article{2013_Wilger,
author = {Dale J. Wilger and Nathan J Gesmundo and David A Nicewicz},
title = {Catalytic hydrotrifluoromethylation of styrenes and unactivated aliphatic alkenes via an organic photoredox system},
journal = {Chemical Science},
year = {2013},
volume = {4},
publisher = {Royal Society of Chemistry (RSC)},
month = {may},
url = {https://doi.org/10.1039/c3sc51209f},
number = {8},
pages = {3160},
doi = {10.1039/c3sc51209f}
}
Cite this
MLA
Copy
Wilger, Dale J., et al. “Catalytic hydrotrifluoromethylation of styrenes and unactivated aliphatic alkenes via an organic photoredox system.” Chemical Science, vol. 4, no. 8, May. 2013, p. 3160. https://doi.org/10.1039/c3sc51209f.