Palladium-Catalyzed Synthesis of 1H-Indenes and Phthalimides via Isocyanide Insertion

Abstract

A new and versatile multicomponent domino strategy has been developed for the synthesis of a series of 1H-indene and phthalimide derivatives from simple and readily available starting materials. This process operating under mild conditions shows a broad substrate scope with moderate to excellent yields.

Divergent Reaction of Isocyanides with o-Bromobenzaldehydes: Synthesis of Ketenimines and Lactams with Isoindolinone Cores

“…As versatile organic synthons, isocyanides have been applied to various transformations. − Our group also carried out a series of studies on their C1 uses in transition-metal-catalyzed reactions, radical reactions and ionic reactions . The use of isocyanides as diatomic building blocks was also developed with transition-metal catalysts such as Ag − and Cu, ,, Lewis acids, and metal-free conditions to generate new chemical bonds with both C and N atoms.…”

Recent Advances in Palladium-Catalyzed Isocyanide Insertions

“…Finally, the compatibility with tertiary, secondary, and primary isocyanides is high, but no further investigations into the isocyanide scope were performed. The same group later reported a similar transformation to phthalimides from o-bromobenzonitriles [117]. In the same year, it was reported that maleimides 260 can be synthesized via a similar oxidative double imidoylation of internal alkynes 163 affording the corresponding maleimides 260 in good yields (Scheme 68) [116].…”

“…Finally, the compatibility with tertiary, secondary, and primary isocyanides is high, but no further investigations into the isocyanide scope were performed. The same group later reported a similar transformation to phthalimides from o-bromobenzonitriles [117]. Follow-up chemistry using this reaction involved the trapping of the transient yniminyl palladium species with carboxylates (Scheme 69) [118].…”

“…Finally, the compatibility with tertiary, secondary, and primary isocyanides is high, but no further investigations into the isocyanide scope were performed. The same group later reported a similar transformation to phthalimides from o -bromobenzonitriles [ 117 ].…”

Recent Advances in the Synthesis of Indenes

“…One more example of Pd catalyzed synthesis of indenes was studied by Wu and Jiang using 2‐(2‐bromophenyl)acetonitriles 89 , isocyanides 90 and amines 91 , as starting materials. The multicomponent reaction proceeds through a migratory insertion of isocyanides under mild conditions and displays wide functional group compatibility (Scheme ).…”