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benzyl radical turned out to present significant differences in
their late stage depending on the substrate and solvent em-
ployed for the transformation.
[7]
Experimental Section
To a flame-dried flask equipped with a magnetic stir bar are added
I, II or III (0.4 mmol, 1 equiv.), alkyl radical precursor 1 or 6
(0.4 mmol, 1.0 equiv.), potassium persulfate (for silane derivatives
only: 0.4 mmol, 1.0 equiv.), Mesitylacridinium perchlorate PCI
(0.02 mmol, 5 mol-%), and anhydrous solvent (0.5 mL). The reaction
is stirred at 25 °C under blue LED irradiation for 16 hours. Conver-
sion is checked by 19F NMR with PhOCF3 as internal standard. The
reaction mixture is partitioned between n-pentane or Et2O and
water. The aqueous layer is extracted with n-pentane or Et2O and
the combined organic layers are dried with MgSO4, filtered and
concentrated to dryness. The crude residue is purified by chroma-
tography to afford the desired product 2, 3 or 4.
[8]
[9]
Acknowledgments
C. G. held a doctoral fellowship from la region Rhône Alpes. The
authors are grateful to the CNRS, ICBMS (UMR 5246), ICL (Insti-
tut de Chimie de Lyon) for financial support. The French Fluor-
ine Network as well as the fédération RENARD and The Départe-
ment de Chimie Moléculaire, Université Grenoble Alpes, are also
acknowledged for their support.
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Keywords: Trifluoromethylselenolation · Acridinium ·
Photochemistry · Alkylsilanes · Potassium
alkyltrifluoroborates · Reaction mechanisms
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Received: July 22, 2019
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