Visible-light-induced direct 3-ethoxycarbonylmethylation of 2-aryl-2H-indazoles in water

A visible-light-driven rhodamine B-catalyzed transition-metal-free 3-ethoxycarbonylmethylation of 2-aryl-2H-indazoles and imidazo[1,2-a]pyridines (40 examples) using commercially available α-bromoesters was realized in water. This protocol features sustainability, operational simplicity, mild reacti...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2022-03, Vol.9 (5), p.1445-1450
Main Authors: Chun-Hua, Ma, Zhao, Lu, He, Xing, Yu-Qin, Jiang, Yu, Bing
Format: Article
Language:English
Subjects:
Aromatic compounds
Natural products
Organic chemistry
Pyridines
Rhodamine
Substrates
Transition metals
Zolpidem
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Summary:A visible-light-driven rhodamine B-catalyzed transition-metal-free 3-ethoxycarbonylmethylation of 2-aryl-2H-indazoles and imidazo[1,2-a]pyridines (40 examples) using commercially available α-bromoesters was realized in water. This protocol features sustainability, operational simplicity, mild reaction conditions, and remarkable substrate scope. Importantly, α-bromoamides are also appropriate substrates for affording 3-carbamylmethylation products. It could be used for the synthesis of the drug zolpidem and the late-stage modification of natural products.
ISSN:2052-4110
2052-4110
DOI:10.1039/d1qo01870a