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RuII-Catalyzed Vinylative Dearomatization of Naphthols via a C(sp2)–H Bond Activation Approach
journal contribution
posted on 2013-11-20, 00:00 authored by Jiang Nan, Zhijun Zuo, Lei Luo, Lu Bai, Huayu Zheng, Yini Yuan, Jingjing Liu, Xinjun Luan, Yaoyu WangIntermolecular
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