Palladium-Catalyzed Intermolecular [4+1] Spiroannulation by C(sp3 )-H Activation and Naphthol Dearomatization
Bojun Tan1, Lu Bai1, Pin Ding1
1Key Laboratory of Synthetic and Natural Functional, Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an, 710127, China.
Abstract:
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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