Palladium-catalyzed ring opening of azabicyclic olefins with organoindium reagents: a simple, clean, and efficient synthesis of functionalized cyclopentenes

Stereoselective Transformations of meso Bicyclic Hydrazines: Versatile Access to Functionalized Aminocyclopentanes

“…The use of these preformed organometallic species enables the stereoselective introduction not only of an allyl function, but also of benzyl groups (Table 12). 67 All of the previous fragmentation reactions occur following a palladium(II) carbometalation step. A different fragmentation pathway, based on a palladium(0)palladium(II) catalytic cycle, has been proposed.…”

Desymmetrization of meso-Bicyclic Hydrazines: An Efficient Strategy towards the Synthesis of Functionalized Cyclopentenes

“…A simple, clean, and efficient synthesis of functionalized cyclopentenes was performed by treating the bicyclic hydrazines with in-situ-generated allyl-and benzylindium species in the presence of a palladium catalyst, a ligand, and a Lewis acid. 34 The reaction with the benzylindium species is shown in Scheme 21. This methodology is noteworthy as it provides access to benzylated cyclopentane derivatives.…”

Indium-Mediated Intramolecular Reaction of N-(2-Iodobenzoyl)azabenzonorbornadienes: A General Access to Dihydrobenzo[c]phenanthridinones

“…In the past few decades, indium-mediated organic reactions have elicited considerable attention. Most synthetically useful indium-mediated reactions are mainly limited to the Ferrier-type alkynylation reactions and allyl alkylation of carbonyl compounds and imine derivatives, , whereas few reports involved the indium-mediated ring-opening reaction of azabicyclic olefins. , Cheng and co-workers reported a Pd-catalyzed ring-opening process of azabicyclic olefins with organic halides via an abnormal Heck-type reaction . Wang et al reported an indium­(III)-catalyzed Heck reaction and suggested that the organoindium intermediate, generated in situ from the reaction of phenyl iodide and indium salt, could easily react with styrene to provide the Heck reaction compound .…”