Palladium/Norbornene Chemistry in the Synthesis of Polycyclic Indolines with Simple Nitrogen Sources

Abstract

<jats:p>An efficient procedure has been developed to synthesize ­indoline derivatives through a palladium-catalyzed Heck reaction/C–H activation/dual amination cascade in one pot. This constitutes the first intermolecular catalytic approach to directly access N-alkylindolines with a broad substrate scope in the absence of any ligands. This method highlights the use of readily available amines and ureas as the required nitrogen sources in building up the indoline core.</jats:p>

Recent Advances in the Synthesis of Five‐membered Nitrogen Heterocycles Induced by Palladium Ions and Complexes

“…In a related study, the synthesis of similar tricyclic indoline derivatives via annulation of iodoarenes with norbornene and amines was reported by Habibi et al [155] The method proceeds efficiently with palladium catalysis in chlorobenzene as solvent to give N-alkylated products with medium to high yields through the generation of C(sp 3 )À C(sp 2 )/C(sp 3 )À N/C(sp 2 )À N bonds in a single step (Scheme 131). Similar results were found with the use of 1,3-bis(alkyl)ureas (58-74 %, 5 examples).…”