University of Regensburg, Faculty of Chemistry and Pharmacy, 93040, Regensburg, Germany.
Angew Chem Int Ed Engl. 2017 Jan 2;56(1):409-412. doi: 10.1002/anie.201610210. Epub 2016 Dec 2.
Heteroaromatic sulfoxides are a frequent structural motif in natural products, drugs, catalysts, and materials. We report a metal-free visible-light-accelerated synthesis of heteroaromatic sulfoxides from sulfinamides and peroxodisulfate. The reaction proceeds at room temperature with blue-light irradiation and allows the C-H sulfinylation of electron-rich heteroarenes, such as pyrroles and indoles. An electrophilic aromatic substitution mechanism is proposed based on the substrate scope, substitution selectivity, and competition experiments with different nucleophiles.
杂芳基亚砜是天然产物、药物、催化剂和材料中常见的结构基序。我们报告了一种无需金属、可见光加速的杂芳基亚砜合成方法，该方法由亚磺酰胺和过二硫酸盐反应得到。该反应在室温下进行，用蓝光照射，可实现富电子杂芳烃（如吡咯和吲哚）的 C-H 亚磺酰化。根据底物范围、取代选择性以及不同亲核试剂的竞争实验，提出了亲电芳香取代反应机理。
