A ring-opening/alkyne–carbonyl
metathesis sequence of alkyne-tethered
cyclobutanones catalyzed by AgSbF6 is realized for the
first time to furnish multisubstituted naphthyl ketones under mild
conditions. A range of substrates decorated with various substituents
at different positions were all well accommodated. Preliminary mechanistic
studies show that silver salt acted as a Lewis acid to facilitate
both C–C cleavage of the cyclobutanone moiety and the subsequent
metathesis between CO and CC bonds.
Despite recent advances in catalytic ring‐opening/cross‐coupling process of o‐halogen tethered phenylcyclobutanones with other partners, single‐component ring expansion of such precursors towards 3‐methylindanones has not been disclosed. We present herein a nickel catalyzed C−C bond reconstruction sequence of o‐bromophenylcyclobutanones using H2O as hydrogen donor, leading to a series of indanones, which can be further converted into other benzene‐fused cyclic compounds.
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