Highly Selective Visible-Light-Induced Cascade Cyclization of Vinyl Sulfoxonium Ylides with Azides: A Novel Synthetic Approach to Trisubstituted Furans

IF 4.6 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Chemistry Frontiers Pub Date : 2025-01-14 DOI:10.1039/d4qo02195a
Jia-Huan Cui, Mei Tan, Jun Zhang, Yan He, Xingguang Li, Pei-Nian Liu
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Abstract

A simple protocol for the synthesis of trisubstituted furans via visible-light-driven regioselective cascade cyclization of vinyl sulfoxonium ylides with azides has been achieved. The reaction proceeds through the formation of a novel α-enone-α’-amide sulfoxonium ylide, which undergoes cyclization upon blue light irradiation to yield trisubstituted furan scaffold. This method offers advantages including the absence of transition metals and photocatalysts, as well as the desired trisubstituted furans were prepared in good to excellent yields.
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高选择性可见光诱导叠氮基亚砜酰乙烯级联环化:合成三取代呋喃的新方法
本文报道了一种简单的合成三取代呋喃的方法,该方法是在可见光驱动的区域选择性级联环化乙烯基亚砜吡啶与叠氮化合物。该反应通过生成一种新的α-烯酮-α ' -酰胺亚砜酰化物进行,该物质在蓝光照射下发生环化反应,生成三取代呋喃支架。该方法的优点包括不需要过渡金属和光催化剂,并且可以以良好的收率制备所需的三取代呋喃。
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来源期刊
Organic Chemistry Frontiers
Organic Chemistry Frontiers CHEMISTRY, ORGANIC-
CiteScore
7.90
自引率
11.10%
发文量
686
审稿时长
1 months
期刊介绍: Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
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