Tetrahedron

A versatile synthetic route to dehydrobenzoannulenes via in situ generation of reactive alkynes

…, RC Chiechi, CA Johnson, DB Kimball, AJ Matzger…

Index: Bell, Michael L; Chiechi, Ryan C; Johnson, Charles A; Kimball, David B; Matzger, Adam J; Brad Wan; Weakley, Timothy J.R; Haley, Michael M Tetrahedron, 2001 , vol. 57, # 17 p. 3507 - 3520

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Citation Number: 65

Abstract

This paper outlines the development of a protocol that allows in situ generation of unstable alkynes under Pd-catalyzed cross-coupling conditions. Cu-mediated intramolecular cyclization of the resultant α, ω-polyynes provides dehydrobenzoannulenes as singular species, in very good overall yields, and in a variety of topologies that are inaccessible by traditional routes or previously available in low yield only. In addition, we will discuss the ...

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