Protocol for Visible-Light-Promoted Desulfonylation Reactions Utilizing Catalytic Benzimidazolium Aryloxide Betaines and Stoichiometric Hydride Donor Reagents.,The Journal of Organic Chemistry

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Protocol for Visible-Light-Promoted Desulfonylation Reactions Utilizing Catalytic Benzimidazolium Aryloxide Betaines and Stoichiometric Hydride Donor Reagents.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-03-03 , DOI: 10.1021/acs.joc.0c00038
Eietsu Hasegawa ₁ , Tsukasa Tanaka ₁ , Norihiro Izumiya ₁ , Takehiro Kiuchi ₁ , Yuuki Ooe ₁ , Hajime Iwamoto ₁ , Shin-Ya Takizawa ₂ , Shigeru Murata ₂

Affiliation

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.

中文翻译：

利用催化苯并咪唑烷氧化甜菜碱和化学计量的氢化供体试剂进行可见光促进的脱磺酰反应的方案。

开发了一种前所未有的光催化系统，该系统由苯并咪唑芳基氧化物甜菜碱（BI + -ArO-）和化学计量的氢化物还原剂组成，用于进行N-磺酰基-吲哚，-酰胺和-胺以及α-磺酰基酮的脱磺酰反应。进行吸收光谱和循环伏安图的测量以及密度泛函理论（DFT）计算以获取机械信息。在催化体系中，通过相应甜菜碱BI + -ArO-的氢化还原就地生成的可见光活化的苯并咪唑啉芳基氧化物（BIH-ArO-）将电子和氢原子同时提供给了底物。

更新日期：2020-03-04

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