Synthesis of cyclophanes via an intermolecular Pd-catalyzed enyne-diyne cross-benzannulation approach

V. Gevorgyan, N. Tsuboya, Y. Yamamoto

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Abstract

Several novel types of cyclophanes were efficiently synthesized via an intermolecular palladium-catalyzed cross-benzannulation of cyclic enynes and diynes. These types of cyclophanes are not accessible through an intramolecular mode of the homo-benzannulation protocol, reported previously. Cyclic reactants (enynes and diynes) were readily prepared in reasonable yields from commercially available materials using known procedures. The fact that the cyclic Z-enyne 29, in contrast to its E-counterpart, underwent benzannulation to produce the cyclophane 28 brought additional support for the necessity of having an E-hydrogen atom at the terminal olefin moiety of nonactivated enynes, which was found previously in the benzannulation of the acyclic susbstrates.

Original languageEnglish (US)
Pages (from-to)2743-2746
Number of pages4
JournalJournal of Organic Chemistry
Volume66
Issue number8
DOIs
Publication statusPublished - Apr 20 2001
Externally publishedYes

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ASJC Scopus subject areas

  • Organic Chemistry

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