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Modular Assembly of Spirocarbocyclic Scaffolds through Pd 0 ‐Catalyzed Intermolecular Dearomatizing [2+2+1] Annulation of Bromonaphthols with Aryl Iodides and Alkynes
Author(s) -
Zuo Zhijun,
Wang Hui,
Fan Liangxin,
Liu Jingjing,
Wang Yaoyu,
Luan Xinjun
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201612127
Subject(s) - alkyne , aryl , indene , annulation , chemistry , catalysis , intermolecular force , palladium , combinatorial chemistry , aryne , stereochemistry , medicinal chemistry , organic chemistry , molecule , alkyl
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 dalesconols A and B from alkyne‐tethered aryl iodides and 1‐bromo‐2‐naphthol.