Enantioselective Synthesis of Acenaphthene-Type Monohydrosilanes

Acenaphthene and its analogues are privileged frameworks in medicinal chemistry and material science. However, the properties of silicon-substituted acenaphthene-type scaffolds are poorly understood. Here, we report a rhodium-catalyzed intramolecular C­(sp3)–H silylation for enantioselective synthes...

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Bibliographic Details
Published inOrganic letters Vol. 27; no. 14; pp. 3622 - 3630
Main Authors Mu, Delong, Zhu, Xinrui, Chen, Jiean
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 11.04.2025
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
enantioselective synthesis
enantioselectivity
heterocyclic compounds
insecticidal properties
materials science
Physical Sciences
Science & Technology
silicon
silylation
RHODIUM
SILICON
HYDROSILYLATION
BONDS
SULFUR
C-H SILYLATION
DESYMMETRIZATION
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Summary:Acenaphthene and its analogues are privileged frameworks in medicinal chemistry and material science. However, the properties of silicon-substituted acenaphthene-type scaffolds are poorly understood. Here, we report a rhodium-catalyzed intramolecular C­(sp3)–H silylation for enantioselective synthesis of acenaphthene-type scaffolds with excellent enantioselectivity and broad substrate scope. This protocol enables facile access to various quaternary stereogenic silicon centers with heterocyclic scaffolds using monohydrosilanes as chiral building blocks. We also synthesized a new silafluofen analogue that shows good insecticidal activity.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.5c00727