Synthesis of [60]Fullerene-Fused Spiroindanes by Palladium-Catalyzed Oxidative Annulation of [60]Fullerene with 2‑Aryl Cyclic 1,3-Dicarbonyl Compounds

A convenient and facile palladium-catalyzed reaction of [60]­fullerene (C60) with 2-aryl cyclic 1,3-dicarbonyl compounds via the enolate-directed sp2 C–H activation and sp3 C–H functionalization has been exploited to synthesize the novel and rare C60-fused spiroindanes for the first time. This react...

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Bibliographic Details
Published inOrganic letters Vol. 18; no. 11; pp. 2616 - 2619
Main Authors Zhou, Dian-Bing, Wang, Guan-Wu
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.06.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FULLERENES
CHEMISTRY
SULFONAMIDES
BOND ACTIVATION
SELECTIVE SYNTHESIS
C-60
HETEROANNULATION
C-H FUNCTIONALIZATION
DERIVATIVES
CHLORIDE
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Summary:A convenient and facile palladium-catalyzed reaction of [60]­fullerene (C60) with 2-aryl cyclic 1,3-dicarbonyl compounds via the enolate-directed sp2 C–H activation and sp3 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.
Bibliography:ObjectType-Article-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01043