Practical synthesis of (Z)-polyaromatic and heteroaromatic vinylacetylenes.

Research paper by Anthony A Hayford, Joseph J Kaloko, Salwa S El-Kazaz, Gwen G Bass, Cheryl C Harrison, Thomas T Corprew

Indexed on: 17 Jun '05Published on: 17 Jun '05Published in: Organic Letters


[reaction: seet text] 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).