It has been established that a Rh /segphos complex catalyzes the [2+2+1] cycloaddition of 1,6-diynes with cyclopropylideneacetamides to give substituted fulvenes in good yields. The reductive complexation of the product fulvenes with RhCl in EtOH furnished the corresponding dinuclear cyclopentadienyl Rh complexes bearing a pendant amide moiety. These Rh complexes were highly active catalysts for oxidative annulation and cyclization through C(sp )-H and C(sp )-H functionalization.
It has been established that a cyclopentadienyl Rh complex with two phenyl groups and a pendant amide moiety catalyzes the formal Lossen rearrangement/[3+2] annulation cascade of N-pivaloyl benzamides and acrylamides with alkynes leading to substituted indoles and pyrroles. Mechanistic studies revealed that this cascade reaction proceeds via not the Lossen rearrangement to form anilides or enamides but C-H bond cleavage, alkyne insertion, and the formal Lossen rearrangement.
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