[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).
Alkenes Q 0083Practical Synthesis of (Z)-Polyaromatic and Heteroaromatic Vinylacetylenes. -Two alternative and general pathways are developed. The synthetic utility of these methods is illustrated by transformation of electron-rich and electron-deficient heteroaromatic as well as aromatic carboxaldehydes to their (Z)-vinylacetylenes in good to excellent yields. -(HAYFORD*, A.; KALOKO, J. J.; EL-KAZAZ, S.; BASS, G.; HARRISON, C.; CORPREW, T.; Org. Lett. 7 (2005) 13, 2671-2673; Dep. Chem., East Carolina Univ., Greenville, NC 27858, USA; Eng.) -Y. Steudel 44-085
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