期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 23, 页码 7813-7817出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201903492
关键词
BINOLs; metal-free catalysis; oxidative coupling; Pummerer reaction; sulfoxide
资金
- EPSRC [EP/M005062/1]
- University of Manchester
- EPSRC [EP/P001386/1, EP/M005062/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [EP/M005062/1, EP/P001386/1] Funding Source: researchfish
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.
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