| MEYER, Andreas U., Tomáš SLANINA, Chang-Jiang YAO a Burkhard KÖNIG. Metal-Free Perfluoroarylation by Visible Light Photoredox Catalysis. ACS Catalysis. WASHINGTON: AMER CHEMICAL SOC, roč. 6, č. 1, s. 369-375. ISSN 2155-5435. doi:10.1021/acscatal.5b02410. 2016. |
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@article{1345777,
author = {Meyer, Andreas U. and Slanina, Tomáš and Yao, ChangandJiang and König, Burkhard},
article_location = {WASHINGTON},
article_number = {1},
doi = {http://dx.doi.org/10.1021/acscatal.5b02410},
keywords = {perfluorophenyl; photocatalysis; visible light; metal-free conditions; C-H arylation; transient spectroscopy},
language = {eng},
issn = {2155-5435},
journal = {ACS Catalysis},
title = {Metal-Free Perfluoroarylation by Visible Light Photoredox Catalysis},
url = {http://pubs.acs.org/doi/abs/10.1021/acscatal.5b02410},
volume = {6},
year = {2016}
}
TY - JOUR
ID - 1345777
AU - Meyer, Andreas U. - Slanina, Tomáš - Yao, Chang-Jiang - König, Burkhard
PY - 2016
TI - Metal-Free Perfluoroarylation by Visible Light Photoredox Catalysis
JF - ACS Catalysis
VL - 6
IS - 1
SP - 369-375
EP - 369-375
PB - AMER CHEMICAL SOC
SN - 21555435
KW - perfluorophenyl
KW - photocatalysis
KW - visible light
KW - metal-free conditions
KW - C-H arylation
KW - transient spectroscopy
UR - http://pubs.acs.org/doi/abs/10.1021/acscatal.5b02410
L2 - http://pubs.acs.org/doi/abs/10.1021/acscatal.5b02410
N2 - Visible light and eosin Y catalyze the direct arylation of simple arenes with fluorinated aryl bromides by a photoredox process. The reaction scope is broad in fluorinated compounds and arenes and the general and simple procedure provides a metal-free alternative for the synthesis of synthetically valuable polyfluorinated biaryl structures. The mild reaction conditions allow a selective reaction with the alkaloid brucine without protection of functional groups illustrating the potential of the process for late stage functionalization. Mechanistic investigations reveal the photoreduction of eosin Y via its triplet state by triethylamine and subsequent electron transfer from the eosin Y radical anion to the polyfluorinated bromoarene, which fragments into the polyfluorinated aryl radical and a bromide anion. A radical chain reaction mechanism was excluded by a quenching factor analysis.
ER -
MEYER, Andreas U., Tomáš SLANINA, Chang-Jiang YAO a Burkhard KÖNIG. Metal-Free Perfluoroarylation by Visible Light Photoredox Catalysis. \textit{ACS Catalysis}. WASHINGTON: AMER CHEMICAL SOC, roč.~6, č.~1, s.~369-375. ISSN~2155-5435. doi:10.1021/acscatal.5b02410. 2016.
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