Organophotocatalyzed Synthesis of Vinyl‐SCF3 and Benzoyl‐SCF3 Using a New N‐(SCF3)(CF3)‐Shelf‐Stable Reagent

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(2023)

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Abstract
We report the photocatalyzed C-SCF3 bond formation using a new shelf-stable PhPh-N-(SCF3)(CF3) reagent I in combination with 4CzIPN as organophotocatalyst under blue LED irradiation. While the synthesis of vinyl-SCF3 is performed in the presence of bromide salts as an activator of reagent I, the synthesis of trifluoromethylthioesters was undertaken using aldehydes as starting material in the presence of a hydrogen atom transfer catalyst (HAT). Preliminary mechanistic investigations including EPR spectroscopy and cyclic voltammetry analysis shed the light on the reaction mechanisms.
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Key words
Trifluoromethylthiolation,Photocatalysis,radicals,EPR,HAT
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