RuII-Catalyzed Vinylative Dearomatization of Naphthols via a C(sp2)–H Bond Activation Approach
journal contributionposted on 20.11.2013, 00:00 by Jiang Nan, Zhijun Zuo, Lei Luo, Lu Bai, Huayu Zheng, Yini Yuan, Jingjing Liu, Xinjun Luan, Yaoyu Wang
Intermolecular annulation reactions of 1-aryl-2-naphthols with internal alkynes proceed efficiently in the presence of a Ru catalyst and a Cu oxidant to generate spirocyclic compounds by sequential cleavage of the C(sp2)-H bond, migratory insertion of the alkyne, and dearomatization of the naphthyl ring. Various spirocyclic molecules bearing an all-carbon quaternary stereocenter could be obtained by this novel method with good yields and excellent regioselectivity, and the current process tolerates a variety of synthetically important functional groups.
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presenceVinylativeyieldinsertionregioselectivityvarietyActivationannulationsequential cleavageVarious spirocyclic moleculesspirocyclic compoundsstereocenterquaternaryNaphtholRu catalystCu oxidantBonddearomatizationalkyneDearomatizationnovel methodarylApproachIntermolecularnaphthyl ringsyntheticallybond