Remote selective decarboxylative difluoroarylmethylation of 8-aminoquinolines under transition metal-free conditions

Guo, Xiaolong; Li, Pingping; Wang, Qi; Wang, Qing; Wang, Luyao

doi:10.1039/d1qo01912k

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Cited by 4 publications

References 76 publications

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tBu₄NCl/K₂S₂O₈ System Induced C‐2 Functionalization of 8‐Aminoquinoline Amides with Primary Alcohols

Zhang

Jin-xiang

et al. 2023

Eur J Org Chem

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A metal and light‐free Minisci‐type acylation approach of 8‐aminoquinoline amides with general primary alcohols was demonstrated under tBu4NCl/K2S2O8 system. Simultaneously, the C2−H alkylation can be realized by accident for special benzyl alcohols bearing strong electron‐donating groups. Most N‐heterocycles were also compatible to afford corresponding acylated products. Furthermore, the mechanism investigation reveals that chlorine radical induced the original ketyl radical generation through abstracting the α‐C−H from the alcohols, then underwent nucleophilic carbon‐centered radicals addition, deprotonation, and oxidation to provide the target acylation products.

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tBu₄NCl/K₂S₂O₈ System Induced C‐2 Functionalization of 8‐Aminoquinoline Amides with Primary Alcohols

Zhang

Jin-xiang

et al. 2023

Eur J Org Chem

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Six-membered ring systems: pyridines and benzo derivatives

Badenock

2023

Progress in Heterocyclic Chemistry

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Visible-Light-Induced Cascade Cyclization of 1-Acryloyl-2-cyanoindole: Access of Difluoroalkylated Pyrrolo[1,2-a]indolediones

Yuan,

Shen,

Guo

et al. 2023

J. Org. Chem.

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An effective method for accessing diverse difluoroalkylated pyrrolo[1,2-a]indolediones via visible-light-induced PhI(OAc)2-promoted cascade difluoroalkylation/cyclization reaction under mild conditions has been established. This method is noteworthy for its use of DMSO–H2O as a green medium at room temperature and avoidance of photocatalysts. The reactions are straightforward to execute and convenient to expand on, provide good to excellent yields, and have good functional group tolerance.

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Remote selective decarboxylative difluoroarylmethylation of 8-aminoquinolines under transition metal-free conditions

Abstract: A facile transition metal-free decarboxylative C4 selective C-H diﬂuoroarylmethylation of 8-aminoquinolines has been developed. This strategy proceeds under simple aqueous conditions and displays a broad substrate scope and excellent functional...

Cited by 4 publications

References 76 publications

tBu₄NCl/K₂S₂O₈ System Induced C‐2 Functionalization of 8‐Aminoquinoline Amides with Primary Alcohols

tBu₄NCl/K₂S₂O₈ System Induced C‐2 Functionalization of 8‐Aminoquinoline Amides with Primary Alcohols

Six-membered ring systems: pyridines and benzo derivatives

Visible-Light-Induced Cascade Cyclization of 1-Acryloyl-2-cyanoindole: Access of Difluoroalkylated Pyrrolo[1,2-a]indolediones

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Remote selective decarboxylative difluoroarylmethylation of 8-aminoquinolines under transition metal-free conditions

Abstract: A facile transition metal-free decarboxylative C4 selective C-H diﬂuoroarylmethylation of 8-aminoquinolines has been developed. This strategy proceeds under simple aqueous conditions and displays a broad substrate scope and excellent functional...

Cited by 4 publications

References 76 publications

tBu4NCl/K2S2O8 System Induced C‐2 Functionalization of 8‐Aminoquinoline Amides with Primary Alcohols

tBu4NCl/K2S2O8 System Induced C‐2 Functionalization of 8‐Aminoquinoline Amides with Primary Alcohols

Six-membered ring systems: pyridines and benzo derivatives

Visible-Light-Induced Cascade Cyclization of 1-Acryloyl-2-cyanoindole: Access of Difluoroalkylated Pyrrolo[1,2-a]indolediones

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tBu₄NCl/K₂S₂O₈ System Induced C‐2 Functionalization of 8‐Aminoquinoline Amides with Primary Alcohols

tBu₄NCl/K₂S₂O₈ System Induced C‐2 Functionalization of 8‐Aminoquinoline Amides with Primary Alcohols