65378-69-0Relevant academic research and scientific papers
Aryl-substituted dimethylbenzimidazolines as effective reductants of photoinduced electron transfer reactions
Hasegawa, Eietsu,Ohta, Taku,Tsuji, Shiori,Mori, Kazuma,Uchida, Ken,Miura, Tomoaki,Ikoma, Tadaaki,Tayama, Eiji,Iwamoto, Hajime,Takizawa, Shin-Ya,Murata, Shigeru
, p. 5494 - 5505 (2015/08/03)
Photoinduced electron transfer (PET) reactions promoted by 2-aryl substituted 1,3-dimethylbenzimidazolines (Ar-DMBIH) were investigated. Excited states of Ar-DMBIH, formed by irradiation using light above 360 nm, initiate PET reductions of various organic substrates, including transformations of epoxy ketones to aldols, free radical rearrangements such as the Dowd-Beckwith ring-expansion and 5-exo hexenyl cyclization, deprotection of N-sulfonyl-indols, and allylation of acyl formates. In these processes, Ar-DMBIH possessing 1-naphthyl, 2-naphthyl, 1-pyrenyl and 9-anthryl substituents formally act as two electron and one proton donors while the hydroxynaphthyl substituted derivative serves as a two electron and two proton donor. On the basis of the results of absorption spectroscopy studies, cyclic voltammetry and DFT calculation, a mechanistic sequence for these reduction reactions is proposed that involves initial photoexcitation of the aryl chromophore of the Ar-DMBIH followed by single electron transfer (SET) to the organic substrate to generate the radical cation of benzimidazoline and the radical anion of the substrate.
2-Hydroxyphenyl-1,3-dimethylbenzimidazolines. Formal two hydrogen atom-donors for photoinduced electron transfer reactions
Hasegawa, Eietsu,Chiba, Naoki,Takahashi, Tomoya,Takizawa, Shinya,Kitayama, Takashi,Suzuki, Toshio
, p. 18 - 19 (2007/10/03)
Both 2-(2′-hydroxyphenyl)-1,3-dimethylbenzimidazoline and 2-(4′-hydroxyphenyl)-1,3-dimethylbenzimidazoline were found to act as formal two hydrogen atom-donors for photoinduced electron transfer reactions of epoxy ketones and other carbonyl compounds.
ORGANOSELENIUM-MEDIATED REDUCTION OF α,β-EPOXY KETONES TO β-HYDROXY KETONES: A NEW ACCESS TO INTER- AND INTRAMOLECULAR ALDOLS
Miyashita, Masaaki,Suzuki, Toshio,Yoshikoshi, Akira
, p. 4293 - 4296 (2007/10/02)
The organoselenium-mediated reduction of α,β-epoxy ketones has been demonstrated to be a promising entry to a variety of cyclic and acyclic aldols.
