jo0c01135_si_001.pdf (16.78 MB)
In Situ-Generated Halogen-Bonding Complex Enables Atom Transfer Radical Addition (ATRA) Reactions of Olefins
journal contribution
posted on 2020-08-07, 02:29 authored by Kazuki Matsuo, Eiji Yamaguchi, Akichika ItohAlthough
organic-based photocatalysts provide an inexpensive, environmentally
friendly alternative, many are incapable of absorption within the
visible wavelength range; this ultimately influences their effectiveness.
Photocatalytic reactions usually proceed via single electron transfer
(SET) or energy transfer (ET) processes from the photoexcited molecules
to the various substrates. In our study, the carbohalogenation of
olefins was accomplished by combining CBr4 and 4-Ph-pyridine
under irradiation. The atom transfer radical addition reaction of
olefins was catalyzed by an in situ-formed photocatalyst via halogen
bonding to afford a variety of products in moderate to good yields.
Essential to the reaction is the formation of a CT complex with the
haloalkene, which triggers charge separation processes and, ultimately,
leads to the formation of the C-centered radical. While taking advantage
of relatively inexpensive, readily available, and environmentally
friendly reagents, the indirect activation of the substrate via the
photoexcited catalyst paves the way for more efficient routes, especially
for otherwise challenging chemical syntheses.
History
Usage metrics
Categories
Keywords
chemical syntheseswavelength range4- Ph-pyridineolefinsenergy transferPhotocatalytic reactionsCBr 4ATRAaddition reactionformationphotoexcited moleculesETelectron transferCTphotoexcited catalystsubstratesitu-formed photocatalystSitu-Generated Halogen-Bonding Comp...organic-based photocatalystsatom transfertriggers charge separation processes
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC