RuII-Catalyzed Vinylative Dearomatization of Naphthols via a C(sp2)–H Bond Activation Approach
Journal of the American Chemical Society2013Vol. 135(46), pp. 17306–17309
Citations Over TimeTop 1% of 2013 papers
Jiang Nan, Zhijun Zuo, Lei Luo, Lu Bai, Huayu Zheng, Yini Yuan, Jingjing Liu, Xinjun Luan, Yao‐Yu Wang
Abstract
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(sp(2))-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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