Copper-mediated C H amination of 2H-indazoles with N–Fluorobenzenesulfonimide

Li, Zhenhua; Ye, Lixian; Cao, Yingyan; Qin, Jinjing; Wang, Wenbiao; Xie, Yuanyuan

doi:10.1016/j.tetlet.2021.153427

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Direct C3–h Functionalization Of 2h-indazoles1

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2024

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Cited by 5 publications

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“…In 2021, Li reported a copper-catalyzed C3-amination of 2 H -indazoles employing commercially available N -fluorobenzenesulfonimide (NFSI) as the amine source (Scheme 33). 54 Mechanistic studies showed that a bis-sulfonylamidyl radical is involved in this transformation, which adds to the C3 position of 2 H -indazole to trigger the reaction.…”

Section: Direct C3–h Functionalization Of 2h-indazolesmentioning

confidence: 99%

Recent advances in C–H functionalization of 2H-indazoles

Yang

Pan

2022

Org. Biomol. Chem.

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Section: Direct C3–h Functionalization Of 2h-indazolesmentioning

confidence: 99%

Recent advances in C–H functionalization of 2H-indazoles

Yang

Pan

2022

Org. Biomol. Chem.

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CH Functionalization of Indazoles

Kumar

Sakhuja

2022

Handbook of CH-Functionalization

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The indazole is an important class of bicyclic nitrogen‐containing heterocycle that forms the core structure of a large number of compounds with potential therapeutic value. Consequently, CH functionalization of this scaffold has been extensively explored using transition metal‐catalyzed and metal‐free CH functionalization strategies. This article provides a perspective on various strategies that have been developed to add a substituent on this heterocycle core and their appropriate coupling partners.

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Metal‐Free Regioselective Direct C(4)−H Amination of Quinazoline with N‐fluorobenzenesulfonimide

Wang,

Lin,

Ying

et al. 2024

ChemPlusChem

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A facile C–H amination of quinazoline employing N‐fluorobenzenesulfonimide (NFSI) as the amination source has been disclosed in the absence of any metal, oxidant or additive. The methodology shows a board range of quinazolines with different functional groups in moderate to good yields up to 87%. Furthermore, gram‐scale reaction, desulfonylation to amine and synthesis of pharmaceutical intermediate were also investigated, which demonstrates potential applications in medicinal chemistry. A plausible amination mechanism is proposed via F+ transfer accompanied by the removal of one molecule of PhSO2F. DFT studies with experimental work suggest that the mechanism via F+ transfer is more favorable than the free radical one.

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Copper-mediated C H amination of 2H-indazoles with N–Fluorobenzenesulfonimide

Cited by 5 publications

References 47 publications

Recent advances in C–H functionalization of 2H-indazoles

Recent advances in C–H functionalization of 2H-indazoles

CH Functionalization of Indazoles

Metal‐Free Regioselective Direct C(4)−H Amination of Quinazoline with N‐fluorobenzenesulfonimide

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