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Synthesis of [60]Fullerene-Fused Spiroindanes by Palladium-Catalyzed Oxidative Annulation of [60]Fullerene with 2-Aryl Cyclic 1,3-Dicarbonyl Compounds
- Source :
- Organic letters. 18(11)
- Publication Year :
- 2016
-
Abstract
- A convenient and facile palladium-catalyzed reaction of [60]fullerene (C60) with 2-aryl cyclic 1,3-dicarbonyl compounds via the enolate-directed sp(2) C-H activation and sp(3) C-H functionalization has been exploited to synthesize the novel and rare C60-fused spiroindanes for the first time. This reaction is easy to perform with broad substrate scope and provides diversified products in 20-50% yields. A plausible reaction mechanism involving the palladium-catalyzed enolate-directed C-H activation and subsequent cyclization has been proposed, and the electrochemistry of the C60-fused spiroindanes has also been investigated.
- Subjects :
- Reaction mechanism
Annulation
Fullerene
010405 organic chemistry
Aryl
Organic Chemistry
chemistry.chemical_element
Substrate (chemistry)
010402 general chemistry
Electrochemistry
01 natural sciences
Biochemistry
Combinatorial chemistry
0104 chemical sciences
Catalysis
chemistry.chemical_compound
chemistry
Physical and Theoretical Chemistry
Palladium
Subjects
Details
- ISSN :
- 15237052
- Volume :
- 18
- Issue :
- 11
- Database :
- OpenAIRE
- Journal :
- Organic letters
- Accession number :
- edsair.doi.dedup.....d78b6e19142d72ae0f363b12f2c77a48