Divergent Synthesis of Pentacyclic Isoindolinones Enabled by Sequential Insertion of Two Different Isocyanides and Acid Promoted Cyclization of Ketenimines
Zhu, Yi-Ming1，,Xu, Xiao-Ping1*(徐小平)，Ji, Shun -Jun1,2*(纪顺俊)
1Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology and Innovation Center for Chemical Science, Soochow University, Suzhou 215123, People’s Republic of China
2Suzhou Baolidi Functional Materials Research Institute, Suzhou 215144, People’s Republic of China
Org. Lett. 2023, 25, 12, 2041–2046
Abstract：A palladium-catalyzed multicomponent reaction involving o-bromobenzaldehydes and two different isocyanides was developed to assemble series of isoindolinones with spiroindolenine or azepinoindole skeletons. This sequential insertion reaction features mild conditions, a wide substrate scope, and high efficiency. Preliminary mechanistic study indicated that the difference in steric hindrance between isocyanide components is crucial when regulating the reaction sequence, whereas the ligand also played an important role during the whole process.
链接：//doi.org/10.1021/acs.orglett.3c00393
