Pd-Catalyzed alkynyl aryl iodide cyclization/alkylation with cyclobutanols

Abstract

A palladium-catalyzed cis-selective carboalkylation of internal alkynes with cyclobutanols is reported, providing a useful and facile approach to alkyl-substituted olefins in moderate to good yields with excellent stereoselectivity. The cascade...

Palladium-Catalyzed Cyclization Coupling with Cyclobutanone-Derived N-Tosylhydrazones: Synthesis of Benzofuran-3-Cyclobutylidenes and Spirocyclobutanes

“…In particular, palladium-catalyzed cyclization of alkynyl haloarenes has attracted great attention . Mechanistically, intramolecular carbopalladation of an alkyne with aryl halide was involved, affording an alkenyl-Pd intermediate, which further coupled with different species, such as boronic acids, organosilicon reagents, C-, N-, and O-nucleophiles, and others . However, the product of these transformations was, in general, limited to 2,3-dihydrobenzofuran, and there are few reports on the formation of structurally defined benzofuran.…”

Homoallyl alcohol as an allylation reagent for termination of the Catellani–Lautens reaction via retro-allylation

“…Based on our ongoing research on the palladium-catalyzed cross-coupling reaction 20,21 and palladium/norbornene cooperative catalysis, 4 e ,14 we envisioned that homoallyl alcohols could be used as termination reagents in Catellani–Lautens reactions. In the current work, we developed a palladium/norbornene-catalyzed amination/allylation reaction by using homoallyl alcohol as the termination reagent to afford ortho -aminated allylbenzene (Scheme 1c).…”

Palladium-catalyzed allylic allenylation of homoallyl alcohols with propargylic carbonates

“…In the course of our ongoing research on the palladium-catalyzed cross-coupling reactions, 4,5,16 we envisioned that homoallyl alcohols could be used as allyl reagents in palladium-catalyzed reaction of propargylic alcohol derivatives. Herein we disclose a palladium-catalyzed allylic allenylation of homoallyl alcohols with propargylic carbonates to access to allyl allenes (Scheme 1c).…”