Anovel palladium-catalyzed [4+ +1] spiroannulation was developed by using aC (sp 3 ) À Ha ctivation/naphthol dearomatization approach.This bimolecular domino reaction of two aryl halides was realized through as equence of cyclometallation-facilitated C(sp 3 )ÀHa ctivation, biaryl crosscoupling,a nd naphthol dearomatization, thus rendering the rapid assembly of anew class of spirocyclic molecules in good yields with broad functional-group tolerance.P reliminary mechanistic studies indicate that CÀHc leavage is likely involved in the rate-determining step,a nd af ive-membered palladacycle was identified as the key intermediate for the intermolecular coupling.Scheme 2. Catalytic processes involving electron-rich palladacycles.
A novel palladium‐catalyzed [4+1] spiroannulation was developed by using a C(sp3)−H activation/naphthol dearomatization approach. This bimolecular domino reaction of two aryl halides was realized through a sequence of cyclometallation‐facilitated C(sp3)−H activation, biaryl cross‐coupling, and naphthol dearomatization, thus rendering the rapid assembly of a new class of spirocyclic molecules in good yields with broad functional‐group tolerance. Preliminary mechanistic studies indicate that C−H cleavage is likely involved in the rate‐determining step, and a five‐membered palladacycle was identified as the key intermediate for the intermolecular coupling.
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