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Palladium-catalyzed dearomative 1,4-difunctionalization of naphthalenes† †Electronic supplementary information (ESI) available. CCDC 1982544-1982545. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/d0sc02816a

ABSTRACT: The dearomative 1,4-difunctionalization of naphthalenes is achieved by imitating the reactivity of simple conjugated dienes in aromatic systems, providing functionalized spirooxindoles in high yields (up to 99%) with exclusive diastereoselectivity. 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 ?-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.

SUBMITTER: Yang P

PROVIDER: S-EPMC7504896 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature

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