Palladium-Catalyzed Skeletal Reorganization of Cyclobutanones Invoving Successive C-C Bond/C-H Bond Cleavage

The utilization of cyclobutanones as the synthon in transition metal catalysis has been made great success. Because C(carbonyl)-C bond of cyclobutanones can be cleaved through strain release. Despite those advancements, the main catalysts in literature are Rh catalysts or Ni catalysts and the reaction with C-H bond is still underdeveloped. Herein, we realized the first palladium-catalyzed skeletal reorganization of cyclobutanones involving successive cleavage of C(carbonyl)-C bonds and C-H bond cleavage, which constitutes an rapid access to diverse indanones. In contrast to the previous Rh-catalytic system, the Pd-catalytic system herein involves different mechanism and features several advantages: 1) no need of directing group to facilitate the C(carbonyl)-C bond cleavage; 2) much milder reaction condition and 3) simplified work-up.