A Ni(II)-catalyzed
tandem cyclopropane ring opening and radical
alkylation of the aromatic ring using unactivated alkyl bromide-tethered
alkylidenecyclopropanes (ACPs) have been described in this paper.
This ring-forming process exhibits a broad substrate scope with a
variety of primary alkyl bromides and aromatic rings, affording diversified
benzo[b]naphtho[1,2-d]azepine derivatives
in moderate-to-excellent yields under mild conditions. Plausible reaction
mechanisms have been proposed on the basis of several control experiments,
including the deuterium labeling examinations. Further derivatization
of the obtained polycyclic product has also been performed.
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