Condensation of Alkynes with Cyclopentadiene via Titanacyclopentadiene Complexes

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Titanocene dichloride reacted with two equiv of alkynes to form bis(cyclopentadienyl)titanacyclopentadiene complexes in excellent yields. Subsequently, addition of azobenzene, in ‘one-pot’ manner, led to the formation of indene derivatives inhigh yields. Various alkynes were applicable for the coupling reaction withcyclopentadienyl ligand. When benzene or polyarene bridged diynes were employed, thecorresponding cyclopentadiene-fused acenes were obtained in good yields. These indeneproducts were treated with BuLi and ZrCl4successively to give bis(indenyl)zirconocenedichloride derivatives in good yields.