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- Title
The Interrupted Pummerer Reaction in a Sulfoxide‐Catalyzed Oxidative Coupling of 2‐Naphthols.
- Authors
He, Zhen; Pulis, Alexander P.; Procter, David J.
- Abstract
A benzothiophene S‐oxide catalyst, generated in situ by sulfur oxidation with H2O2, 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.
- Subjects
PUMMERER rearrangement; SULFUR; OXIDATION; BIOACTIVE compounds; CATALYSIS
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 23, p7895
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201903492