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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,...
Coupling of 2-functionalized 1-naphthyl halides with gaseous acetylene, (trialkylsilyl)acetylenes, and aryl acetylenes under Pd(PPh 3 ) 4 or Pd(PPh 3 ) 4 /CuI catalysis has been investigated to prepare 1-naphthyl-, 1-(1-naphthyl)-2-phenyl-, and 1,2-bis(1-naphthyl)acetylenes with various ortho substituents, i.e., the -CH 3 , -CH 2 OH, -CO 2 Me,...
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