Tetrahedron

Transition metal control in the reaction of alkyne-substituted phenyl iodides with terminal alkynes: Sonogashira coupling vs cyclic carbopalladation

…, IG Stará, I Starý, A Kollárovič, D Šaman, P Fiedler

Index: Teply, Filip; Stara, Irena G.; Stary, Ivo; Kollarovic, Adrian; Saman, David; Fiedler, Pavel Tetrahedron, 2002 , vol. 58, # 44 p. 9007 - 9018

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Citation Number: 20

Abstract

Reaction between terminal alkynes and phenyl iodides bearing a tethered alkyne unit can be effectively controlled by the nature of a transition metal catalyst. Whereas the use of Pd (0)/Cu (I) promotes the expected Sonogashira coupling to give phenyl alkynes, the absence of the copper co-catalyst triggers a palladium-mediated cyclisation providing 1, 2- dihydroacenaphthylene, 1H, 3H-benzo [de] isochromene,(1Z)-1-(2-propynylidene)-2, 3- ...