期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 5, 页码 1474-1478出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201813202
关键词
C-H activation; cyclization; dearomatization; palladium; spiro compounds
资金
- National Science Foundation of China [21672169]
- Key Science and Technology Innovation Team of Shaanxi Province [2017KCT-37]
- Key Laboratory Project of Xi'an [201805058ZD9CG42]
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.
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