A Copper Halide Promoted Regioselective Halogenation of Coumarins Using N-Halosuccinimide as Halide Source

Abstract A safe, convenient, and regioselective synthesis of 3-halo coumarins using a metal halide (CuX 2 alone or with ZnX 2 ) promoted halogenation with N -halosuccinimide (NXS) as halide source is reported. The synthesis involved the steady in situ generation of highly reactive positive halogen (...

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Bibliographic Details
Published in:Synlett 2019-03, Vol.30 (5), p.630-634
Main Authors: Su, Jinling, Zhang, Yan, Chen, Mingren, Li, Weiming, Qin, Xuewei, Xie, Yanping, Qin, Lixiao, Huang, Shihua, Zhang, Min
Format: Article
Language:English
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Summary:Abstract A safe, convenient, and regioselective synthesis of 3-halo coumarins using a metal halide (CuX 2 alone or with ZnX 2 ) promoted halogenation with N -halosuccinimide (NXS) as halide source is reported. The synthesis involved the steady in situ generation of highly reactive positive halogen (X + ) by the coordination of copper or zinc with the N -halosuccinimide and subsequent electrophilic aromatic substitution of the electron-deficient coumarins. This procedure works well also for the halogenation of less electron-rich naphthoquinones, flavones, and methoxypsoralen in moderate to quantitative yields. This protocol features simple experimental conditions using readily available inexpensive reagents and provides a convenient approach to the chlorination or bromination of some useful heteroaromatic compounds.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0037-1612080