o-Dihaloarenes acting as aryne precursors react with acetylenes and nitriles catalyzed by the NiBr2(dppe)/dppe/Zn system to give substituted naphthalene, phenanthridine or triphenylene derivatives depending on the reaction conditions in moderate to excellent yields with good tolerance of functional groups.
The NiBr2(dppe)–Zn system effectively catalyzes the [2 + 2 + 2] cocyclotrimerization of arynes with diynes, leading to substituted naphthalene derivatives in moderate to good yields. This cocyclotrimerization reaction shows excellent tolerance of functional groups and leads to products of 5- to 7-membered fused-ring sizes
The NiBr2(dppe)–Zn system effectively catalyzes the [2+2+2] cocyclotrimerization of arynes with allenes, leading to 10-methylene-9,10-dihydrophenanthrenes in moderate to good yields. The cocyclotrimerization is highly selective with only the internal double bond of the allenes being involved in the reaction.