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2024 , Vol. 44 >Issue 7: 2265 - 2273

DOI: https://doi.org/10.6023/cjoc202312025

研究论文

可见光诱导铁催化氮杂环的羟甲基化

  • 傅艳华 ,
  • 徐畅 ,
  • 张超 ,
  • 王怡莎 ,
  • 冯高峰
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  • 绍兴文理学院 浙江省精细化学品绿色替代技术研究重点实验室 浙江绍兴 312000

收稿日期: 2023-12-02

  修回日期: 2024-02-08

  网络出版日期: 2024-04-10

基金资助

国家自然科学基金(21676166); 国家自然科学基金(21302130)

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Visible-Light Induced Iron-Catalyzed Hydroxymethylation of N-Heterocycles

  • Yanhua Fu ,
  • Chang Xu ,
  • Chao Zhang ,
  • Yisha Wang ,
  • Gaofeng Feng
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  • Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing, Zhejiang 312000
* E-mail:

Received date: 2023-12-02

  Revised date: 2024-02-08

  Online published: 2024-04-10

Supported by

National Natural Science Foundation of China(21676166); National Natural Science Foundation of China(21302130)

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摘要

以甲醇为羟甲基化试剂, 发展了一种铁催化可见光诱导氮杂环羟甲基化新方法. 以FeCl3为催化剂, 2-甲基异烟酸为配体, 对甲苯磺酸为酸, 空气为氧化剂, 甲醇和水为溶剂, 在可见光(427 nm)诱导下实现了多种取代喹啉、异喹啉、吡啶、苯并噻唑和伏立康唑的羟甲基化, 展现了该方法优秀的底物普适性. 该方法具有反应条件绿色、反应原子经济性好及操作简单等优点, 在药物分子或生物活性分子后续结构修饰中具有潜在的应用价值.

关键词： 铁催化; 羟甲基化; 可见光催化; 氮杂环

本文引用格式

傅艳华 , 徐畅 , 张超 , 王怡莎 , 冯高峰 . 可见光诱导铁催化氮杂环的羟甲基化[J]. 有机化学, 2024 , 44(7) : 2265 -2273 . DOI: 10.6023/cjoc202312025

Abstract

A new strategy for iron-catalyzed visible-light induced hydroxymethylation of N-heterocycles with methanol under mild conditions was developed. By employing FeCl3 as the catalyst, 2-methylisonicotinic acid as the ligand, TsOH as the acid, air as the oxidant, and aqueous MeOH as the solvent, varieties of substituted quinolines, isoquinolines, pyridines, benzothiazole and voriconazole were hydroxymethylated smoothly in good to excellent yields, exhibiting good substrate scope. This strategy features green reaction conditions, excellent atom-economy and simple operations. It has potential applicable value in late-stage structure modification of drug molecule.

Key words： iron catalysis; hydroxymethylation; visible-light catalysis; N-heterocycle

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