Journal
TETRAHEDRON LETTERS
Volume 46, Issue 49, Pages 8599-8603Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2005.09.170
Keywords
lewis acid; catalyst; halo-arylation; N-Halpsuccinimide; chromanones; chromans; quinolones; tetrahydroquinolines; tetralins
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Lewis acid catalyzed intramolecular halo-arylation of tethered alkenes was performed using N-halosuccinimide (NXS) as the halogen source. Among the Lewis acids investigated, Sm(OTf)(3) was found to be the best catalyst. This catalytic process provides a general method for the regio- and stereoselective synthesis of annulated arene heterocycles and carbocycles Such as 2-chromanones, chromans, 2-quinolones, tetrahydroquinolines and tetralins possessing a halo-functionality. (c) 2005 Elsevier Ltd. All rights reserved.
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