Practical Synthesis of (Z)-Polyaromatic and Heteroaromatic Vinylacetylenes
journal contributionposted on 23.06.2005, 00:00 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).