Journal of Organic Chemistry p. 4344 - 4353 (2020)
Update date:2022-08-10
Topics:
Hasegawa, Eietsu
Tanaka, Tsukasa
Izumiya, Norihiro
Kiuchi, Takehiro
Ooe, Yuuki
Iwamoto, Hajime
Takizawa, Shin-Ya
Murata, Shigeru
An unprecedented photocatalytic system consisting of benzimidazolium aryloxide betaines (BI+-ArO-) and stoichiometric hydride reducing reagents was developed for carrying out desulfonylation reactions of N-sulfonyl-indoles,-amides, and-amines, and α-sulfonyl ketones. Measurements of absorption spectra and cyclic voltammograms as well as density functional theory (DFT) calculations were carried out to gain mechanistic information. In the catalytic system, visible-light-activated benzimidazoline aryloxides (BIH-ArO-), generated in situ by hydride reduction of the corresponding betaines BI+-ArO-, donate both an electron and a hydrogen atom to the substrates. A modified protocol was also developed so that a catalytic quantity of more easily prepared hydroxyaryl benzimidazolines (BIH-ArOH) is used along with a stoichiometric hydride donor to promote the photochemical desulfonylation reactions.
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