American Chemical Society
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Practical Synthesis of (Z)-Polyaromatic and Heteroaromatic Vinylacetylenes

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journal contribution
posted on 2005-06-23, 00:00 authored by Anthony Hayford, Joseph Kaloko, Salwa El-Kazaz, Gwen Bass, Cheryl Harrison, Thomas Corprew
Two synthetic routes to several (Z)-polyaromatic and heteroaromatic substituted vinylacetylenes are described. The nature of aryl- or heteroaryl-substituted carboxaldehyde used as starting material dictated the choice of Wittig salt employed. A very attractive way to construct polyaromatic and pyridine-containing enynes is the reaction of polyaromatic and pyridine-containing aldehydes with bromomethyltriphenylphosphonium bromide in the presence of potassium tert-butoxide followed by a Sonogashira desilylation procedure (method B).