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Chinese Journal of Organic Chemistry >

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

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

ARTICLES

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
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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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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

Cite this article

Yanhua Fu , Chang Xu , Chao Zhang , Yisha Wang , Gaofeng Feng . Visible-Light Induced Iron-Catalyzed Hydroxymethylation of N-Heterocycles[J]. Chinese Journal of Organic Chemistry, 2024 , 44(7) : 2265 -2273 . DOI: 10.6023/cjoc202312025

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