Using the optimized conditions from entry 8, we found it was possible to prepare several coumarin 20-24 and quinolone 25-27 derivatives (Figure ). Both electron-withdrawing and electron-donating substituents were found to be well tolerated, with all coumarin and quinolone derivates being delivered in good to excellent yields. Finally, because the key step in initiating the catalytic cycle is an alkylation, we reasoned that other electrophiles should also be subject to metathesis with olefins under this paradigm. For example, we hypothesized that alcohol 28 might alkylate a diazene catalyst under ionizing conditions. Indeed, we found that treatment of 28 with 1.0 equiv diazene 17 and 2.0 equiv TFA in a wet acetonitrile solution at 120 °C for 12 h gave rise to phenanthrene (15) in 78% yield (eq 1). Benzo [c]cinnoline (18) furnished the product in more modest yield (48%); however, we were unable to achieve catalyst turnover. Neither benzo [c]cinnolines 21 nor 22 led to any product, which we attribute to the poor nucleophilicity of 21 and the difficulty of 22 undergoing the requisite 1,3-prototropic shift in the absence of base.