Fluoroalkylselenolation of Alkyl Silanes/Trifluoroborates under Metal-Free Visible-Light Photoredox Catalysis
Herein a metal-free fluoroalkylselenolation of alkylsilanes as well as potassium alkyltrifluoroborates under visible light photocatalysis is disclosed. The developed methodologies are performed under mild conditions, room temperature in the presence of an organic photocatalyst and blue LED irradiation. Mechanistic investigations including luminescence and EPR spectroscopy allow us to shed light on both mechanisms.
Synthesis of Polysubstituted Iodoarenes Enabled by Iterative Iodine-Directed para and ortho C?H Functionalization
Among halogenated aromatics, iodoarenes are unique in their ability to produce the bench-stable halogen(III) form. Earlier, such iodine(III) centers were shown to enable C?H functionalization ortho to iodine via halogen-centered rearrangement. The broader implications of this phenomenon are explored by testing the extent of an unusual iodane-directed para C?H benzylation, as well as by developing an efficient C?H coupling with sulfonyl-substituted allylic silanes. Through the combination of the one-shot nature of the coupling event and the iodine retention, multisubstituted arenes can be prepared by sequentially engaging up to three aromatic C?H sites. This type of iodine-based iterative synthesis will serve as a tool for the formation of value-added aromatic cores.
Wu, Yichen,Bouvet, Sébastien,Izquierdo, Susana,Shafir, Alexandr
supporting information
p. 2617 - 2621
(2019/01/04)
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