In:
Synlett, Georg Thieme Verlag KG, Vol. 30, No. 05 ( 2019-03), p. 630-634
Abstract:
A safe, convenient, and regioselective synthesis of 3-halo coumarins using a metal halide (CuX2 alone or with ZnX2) 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.
Type of Medium:
Online Resource
ISSN:
0936-5214
,
1437-2096
DOI:
10.1055/s-0037-1612080
Language:
English
Publisher:
Georg Thieme Verlag KG
Publication Date:
2019
detail.hit.zdb_id:
2042012-2
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