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Efficient synthesis of 2- and 3-substituted indenes from 2-bromobenzyl bromide through an enolate alkylation/Cr(II)/Ni(II)-mediated carbonyl addition sequence

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
40
Issue
42
Identifiers
DOI: 10.1016/s0040-4039(99)01541-5

Abstract

Abstract An efficient new synthesis of 2- and 3-substituted indenes has been developed based on the nickel-catalyzed chromium(II)-promoted addition of aryl bromides to a tethered ketone carbonyl. Several tethered bromoaryl ketones were prepared through enolate alkylation of acyclic or cyclic ketones with 2-bromobenzyl bromide. Nozaki-Takai-Hiyama-Kishi closure of the resulting bromoaryl ketones followed by acid promoted dehydration gave substituted indenes in overall yields for the three-step sequence ranging from 29 to 58%.

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