Blue Light/NIS-Promoted Amino-Selenylation of Alkenes with Amides and Diselenides

IF 2.1 3区化学 Q3 CHEMISTRY, INORGANIC & NUCLEAR

Journal of Organometallic Chemistry Pub Date : 2025-05-10 DOI:10.1016/j.jorganchem.2025.123716

Yixin Luo , Linsheng Zhong , Meng Ding , Qingle Zeng

引用次数: 0

Abstract

With benzamides as a stable and readily available nitrogen source, a blue light/iodosuccinimide (NIS)-promoted three-component reaction of alkenes under ambient air conditions at room temperature has been developed, which is a novel protocol for the direct synthesis of β-seleno amides. Through this three-component reaction, arylamido/alkylamido and arylselenium groups were introduced into styrenes at the same time, and a series of β-seleno amides (22 target compounds) in 30–70 % yields were obtained. An example of further transformation of the products to 2,5-diphenyl-1,3-oxazoline was demonstrated. A feasible free radical reaction mechanism is proposed based on control experiments and HRMS-captured TEMPO-adduct. In addition, β-thio amides could also synthesized via a similar protocol using diaryl disulfides, albeit in lower yields.

查看原文本刊更多论文

蓝光/ nis促进烯烃与酰胺和二硒化物的氨基硒化反应

以苯并胺为稳定、易获得的氮源，在室温条件下，采用蓝光/碘琥珀酰亚胺（NIS）催化烯烃的三组分反应，为直接合成β-硒胺提供了一种新方案。通过该三组分反应，将芳基胺/烷基胺和芳基硒基团同时引入苯乙烯中，得到了一系列收率为30 - 70%的β-硒酰胺（22个目标化合物）。并举例说明了该产物进一步转化为2,5-二苯基-1,3-恶唑啉的方法。基于对照实验和hrms捕获的tempo -加合物，提出了一种可行的自由基反应机理。此外，β-硫酰胺也可以通过类似的方法用二芳基二硫化物合成，尽管产量较低。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

来源期刊

Journal of Organometallic Chemistry 化学-无机化学与核化学

CiteScore

4.40

自引率

8.70%

发文量

221

审稿时长

36 days

期刊介绍： The Journal of Organometallic Chemistry targets original papers dealing with theoretical aspects, structural chemistry, synthesis, physical and chemical properties (including reaction mechanisms), and practical applications of organometallic compounds. Organometallic compounds are defined as compounds that contain metal - carbon bonds. The term metal includes all alkali and alkaline earth metals, all transition metals and the lanthanides and actinides in the Periodic Table. Metalloids including the elements in Group 13 and the heavier members of the Groups 14 - 16 are also included. The term chemistry includes syntheses, characterizations and reaction chemistry of all such compounds. Research reports based on use of organometallic complexes in bioorganometallic chemistry, medicine, material sciences, homogeneous catalysis and energy conversion are also welcome. The scope of the journal has been enlarged to encompass important research on organometallic complexes in bioorganometallic chemistry and material sciences, and of heavier main group elements in organometallic chemistry. The journal also publishes review articles, short communications and notes.