- A versatile synthetic route to dehydrobenzoannulenes via in situ generation of reactive alkynes
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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 solid-state structure and reactivity of these macrocycles, as well as the ability of the planar dehydrobenzoannulenes to support weak induced ring currents.
- Bell, Michael L,Chiechi, Ryan C,Johnson, Charles A,Kimball, David B,Matzger, Adam J,Brad Wan,Weakley, Timothy J.R,Haley, Michael M
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p. 3507 - 3520
(2007/10/03)
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