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The Interrupted Pummerer Reaction in a Sulfoxide‐Catalyzed Oxidative Coupling of 2‐Naphthols
Author(s) -
He Zhen,
Pulis Alexander P.,
Procter David J.
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201903492
Subject(s) - benzothiophene , sulfoxide , catalysis , chemistry , pummerer rearrangement , oxidative coupling of methane , sulfur , reactivity (psychology) , photochemistry , organic chemistry , medicine , acetic anhydride , alternative medicine , pathology , thiophene
A benzothiophene S‐oxide catalyst, generated in situ by sulfur oxidation with H 2 O 2 , mediates the oxidative coupling of 2‐naphthols. Key to the catalytic process is the capture and inversion of reactivity of a 2‐naphthol partner, using an interrupted Pummerer reaction of an unusual benzothiophene S‐oxide, followed by subsequent coupling with a second partner. The new catalytic manifold has been showcased in the synthesis of the bioactive natural products, (±)‐nigerone and (±)‐isonigerone. Although Pummerer reactions are used widely, their application in catalysis is rare, and our approach represents a new catalytic manifold for metal‐free C−C bond formation.