Table 1. Development of a Catalytic [2 + 2 + 2] Cycloaddition.

^aExperimental procedures provided in the Supporting Information. Nitrile: 2-methoxy-5-pyridine carbonitrile.

^bSolvents were degassed by bubbling argon for 20 min prior to use. 1,2-DME: dimethoxyethane. 1,2-DCE: dichloroethane. 1,2-DCB: dichlorobenzene. TCE: trichloroethylene. DMA: dimethylacetamide.

^c1,4-Dioxane, pyridine, and DMA gave <2% conversion.

^dAdditives at 50 mol %.

^eConversions determined by ¹H NMR spectroscopy.

^fReaction ran without irradiation.