75354-08-4Relevant articles and documents
Photocatalytic Giese-Type Reaction with Alkylsilicates Bearing C,O-Bidentate Ligands
Morofuji, Tatsuya,Matsui, Yu,Ohno, Misa,Ikarashi, Gun,Kano, Naokazu
supporting information, p. 6713 - 6718 (2021/02/26)
Herein, a photocatalytic Giese-type reaction with alkylsilicates bearing C,O-bidentate ligands as stable alkyl radical precursors has been reported. The alkylsilicates were prepared in one step from organometallic reagents. Not only primary, secondary, and tertiary alkyl radicals, but also elusive methyl radicals, could be generated by using the present reaction system. The generated radicals were trapped by electron-deficient olefins bearing various functional groups to give the desired alkyl adducts. The silicon byproduct can be recovered after the photoreaction. The radical generation process was investigated by theoretical calculations, which provided an insight into the facile generation of methyl radicals from methylsilicate bearing C,O-bidentate ligands.
Hydrogen Atom Transfer Reactions via Photoredox Catalyzed Chlorine Atom Generation
Rohe, Samantha,Morris, Avery O.,McCallum, Terry,Barriault, Louis
supporting information, p. 15664 - 15669 (2018/10/26)
The selective functionalization of chemically inert C?H bonds remains to be fully realized in achieving organic transformations that are redox-neutral, waste-limiting, and atom-economical. The catalytic generation of chlorine atoms from chloride ions is one of the most challenging redox processes, where the requirement of harsh and oxidizing reaction conditions renders it seldom utilized in synthetic applications. We report the mild, controlled, and catalytic generation of chlorine atoms as a new opportunity for access to a wide variety of hydrogen atom transfer (HAT) reactions owing to the high stability of HCl. The discovery of the photoredox mediated generation of chlorine atoms with Ir-based polypyridyl complex, [Ir(dF(CF3)ppy)2(dtbbpy)]Cl, under blue LED irradiation is reported.
Redox-economical radical generation from organoborates and carboxylic acids by organic photoredox catalysis
Chinzei, Tatsuya,Miyazawa, Kazuki,Yasu, Yusuke,Koike, Takashi,Akita, Munetaka
, p. 21297 - 21300 (2015/03/18)
A simple generation method of carbon radicals via 1e-oxidation of organotrifluoroborates and carboxylic acids by the action of an organophotoredox catalyst, 9-mesityl-10-methylacridinium perchlorate ([Acr+-Mes]ClO4), has been developed. This organophotocatalytic protocol is amenable to radical C-C bond formation with electron-deficient olefins.