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Palladium‐Catalyzed Intermolecular [4+1] Spiroannulation by C(sp 3 )−H Activation and Naphthol Dearomatization
Author(s) -
Tan Bojun,
Bai Lu,
Ding Pin,
Liu Jingjing,
Wang Yaoyu,
Luan Xinjun
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201813202
Subject(s) - chemistry , palladium , intermolecular force , aryl , catalysis , halide , molecule , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , alkyl
Abstract A novel palladium‐catalyzed [4+1] spiroannulation was developed by using a C(sp 3 )−H activation/naphthol dearomatization approach. This bimolecular domino reaction of two aryl halides was realized through a sequence of cyclometallation‐facilitated C(sp 3 )−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.