Palladium-catalyzed dearomative 1,4-difunctionalization of naphthalenes
Ping Yang1, Chao Zheng1, Yu-Han Nie1
1State Key Laboratory of Organometallic Chemistry , Center for Excellence in Molecular Synthesis , Shanghai Institute of Organic Chemistry , University of Chinese Academy of Sciences , Chinese Academy of Sciences , 345 Lingling Lu , Shanghai 200032 , China .
Abstract:
A highly diastereoselective dearomatization of naphthalenes via a Pd-catalyzed 1,4-difunctionalization reaction is described. In the presence of a commercially available palladium precursor and ligand, intramolecular dearomative Heck-type insertion provides π-allylpalladium intermediates which are readily captured by a series of nucleophiles in excellent yields (up to 99%). This reaction features mild conditions, broad substrate scope, and useful transformations of the products.
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