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. 2021 Nov 29;6(49):34044-34055.
doi: 10.1021/acsomega.1c05455. eCollection 2021 Dec 14.

Hypervalent Iodine(III)-Promoted C3-H Regioselective Halogenation of 4-Quinolones under Mild Conditions

Fang Yang  1 , Xiaoqing Wang  2 , Wenzhuo Zhao  1 , Fei Yu  1 , Zhengsen Yu  1
Affiliations

Hypervalent Iodine(III)-Promoted C3-H Regioselective Halogenation of 4-Quinolones under Mild Conditions

Fang Yang et al. ACS Omega. .

Abstract

A simple and practical protocol for the C3-H regioselective halogenation of 4-quinolones by the action of potassium halide salt and PIFA/PIDA in good to excellent yields was developed. The current approach provides feasible access to the diversity of C3-halgenated 4-quinolones at room temperature with high regioselectivity and good functional group tolerance, from which bioactive compounds can be easily constructed. Moreover, the current method featured eco-friendly, operational convenience and is suitable for halogenation in a gram scale of 4-quinolones in water without sacrificing yields.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Representative active molecules containing 4-quinolone motifs.
Scheme 1
Scheme 1. (a–d) Strategies for the Direct C3–H Functionalization of 4-Quinolones
Scheme 2
Scheme 2. Gram-Scale Preparation of 3-Halo-4-quinolones in Water
Scheme 3
Scheme 3. (a–d) Controlled Experiments and Plausible Reaction Mechanism
See this image and copyright information in PMC

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