Abstract
Computational studies at the B3LYP-D3(BJ) level were performed to explore the mechanism and migratorial selectivity of Fe-catalyzed 2,3-disubstituted azaindole formation from β, β-disubstituted tetrazole and mechanistic details of key steps in this reaction are compared to those in Rh2-catalyzed indole formation. The calculated results show: Fe-catalyzed spirocyclization proceeds via a radical pathway, which is contrary to Rh2-catalyzed spirocyclization that occurs via a carbocation pathway; the migration of C→C significantly prefers to that of C→N due to far lower breakage extents of Fe-N and CC bonds. In addition, the comparisons of uncatalyzed vs. catalyzed N2 extrusion and C→C migration show that iron porphyrin catalyst can lower activation energies of these two steps.
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