通过硫属元素键与梅本试剂介导的可见光驱动的硒代糖苷O-糖基化反应。
A Visible-Light-Driven O-Glycosylation with Selenoglycosides Mediated by Chalcogen Bonding to Umemoto's Reagent.
作者信息
Valenzuela Erik Alvarez, Duong Tiffany, Pradeep Vinayak, He Xuxian, Dobson Jacob M, Lee Semin, Lopata Kenneth, Ragains Justin R
机构信息
Department of Chemistry, Louisiana State University, 232 Choppin Hall, Baton Rouge, LA, 70803, USA.
Department of Chemistry and Physical Sciences, Nicholls St. University, 906 East 1st St., Thibodaux, LA, 70301, USA.
出版信息
Angew Chem Int Ed Engl. 2025 Jul 21;64(30):e202508424. doi: 10.1002/anie.202508424. Epub 2025 May 19.
The activation of chalcogenoglycosides for O-glycosylation typically involves strong electrophiles requiring low temperature. Herein, we demonstrate that visible-light irradiation of selenoglycosides in the presence of Umemoto's reagent results in often high-yielding O-glycosylation. We provide evidence that this process is mediated by a novel mode of reactivity, specifically photoinduced electron transfer within a chalcogen-bonded complex.
用于O-糖基化的硫属元素糖苷的活化通常涉及需要低温的强亲电试剂。在此，我们证明在梅本试剂存在下对硒糖苷进行可见光照射通常会产生高产率的O-糖基化。我们提供的证据表明，这一过程是由一种新型反应模式介导的，具体而言是硫属元素键合配合物内的光致电子转移。
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