Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 10, Pages 2767-2771Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201612127
Keywords
C-H activation; dearomatization; homogeneous catalysis; palladium; spiroannulation
Categories
Funding
- NSFC [21672169, 61605158]
- 1000 Youth Talents Plan
- Education Department of Shaanxi Province [12JS113, 16JK1790]
- Northwest University [YZZ15004]
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A novel palladium(0)-catalyzed dearomatizing [2+2+1] spiroannulation of 1-bromo-2-naphthols with aryl iodides and alkynes was developed for the rapid assembly of spiro[indene-1,1'-naphthalen]-2'-ones. This three-component cascade reaction was realized through consecutive Catellani-type C-H activation, unsymmetrical biaryl coupling, alkyne migratory insertion, and arene dearomatization. The potential utility of our method is illustrated by the one-step construction of the polycyclic skeletons of dalesconolsA and B from alkyne-tethered aryl iodides and 1-bromo-2-naphthol.
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