Issue 14, 2023

Regioselective C–H chalcogenylation and halogenation of arenes and alkenes under metal-free conditions

Abstract

The reactions of direct Csp2–H chalcogenylation and halogenation of N-arylpyrrolidone under the action of PIFA without a directing group and under metal-free conditions were reported in this paper. Diphenyl selenide/sulfur and selenium phenyl halides were used as reaction reagents to obtain chalcogenylated and halogenated N-arylpyrrolidone products, respectively. The mechanistic studies indicated that a radical pathway was likely involved in these reactions. Preliminary antitumor tests showed that these compounds have moderate to potent activities against human acute leukemia cells K562 in vitro, which may be used as lead compounds for subsequent research.

Graphical abstract: Regioselective C–H chalcogenylation and halogenation of arenes and alkenes under metal-free conditions

Supplementary files

Article information

Article type
Communication
Submitted
30 Jan 2023
Accepted
21 Feb 2023
First published
21 Mar 2023

Org. Biomol. Chem., 2023,21, 2910-2916

Regioselective C–H chalcogenylation and halogenation of arenes and alkenes under metal-free conditions

B. Li, M. Hu, J. Ge, W. Xu, J. Wu, Y. Tong, Z. Zhao, X. Liu and L. He, Org. Biomol. Chem., 2023, 21, 2910 DOI: 10.1039/D3OB00150D

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