Catalysis

Intramolecular force

Aldol condensation

Aldol reaction

Carbonylation

Carbon monoxide

Substrate (aquarium)

Geology

Oceanography

Medicinal chemistry

Combinatorial chemistry

Organic chemistry

Cyclopentenone

Benzyl bromide

Chemistry

Bromide

Nickel

Organic Letters

Herein, we reported a Ni-catalyzed carbonylation of cyclopropanol with benzyl bromide to afford multisubstituted cyclopentenone under 1 atm of CO. The reaction proceeds through cascade carbonylation of benzyl bromides, followed by generation of nickel homoenolate from cyclopropanols via β-C elimination to afford 1,4-diketones, which undergoes intramolecular Aldol condensation to furnish highly substituted cyclopentenone derivatives in moderate to good yields. The reaction exhibits high functional group tolerance with broad substrate scope.

Nickel-Catalyzed Carbonylation of Cyclopropanol with Benzyl Bromide for Multisubstituted Cyclopentenone Synthesis