Diisobutylaluminum hydride-promoted cyclization of benzyl and phenylsilyl ethers bearing a 2-(trimethylsilyl)ethynyl group: syntheses of indenes and benzosiloles

[Display omitted] •DIBAL-H promotes the cyclization of o-(silylethynyl)benzyl ethers to 2-silylindenes.•Diethylaluminum chloride assists the DIBAL-H-promoted cyclization.•The DIBAL-H-promoted cyclization is applicable to the synthesis of benzo[b]siloles. The reaction of o-[2-(trimethylsilyl)ethynyl]...

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Bibliographic Details
Published inTetrahedron letters Vol. 57; no. 31; pp. 3571 - 3574
Main Authors Kinoshita, Hidenori, Fukumoto, Hiroki, Tohjima, Takayuki, Miura, Katsukiyo
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 03.08.2016
Elsevier
Subjects
Benzocyclization
Benzosilole
Chemistry
Chemistry, Organic
Diisobutylaluminum hydride
Indene
Physical Sciences
Science & Technology
Benzosilole
Indene
Benzocyclization
Diisobutylaluminum hydride
POLYMERS
GOLD
O-(TRIMETHYLSILYLETHYNYL)STYRENES
CLEAVAGE
BOND
DERIVATIVES
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Summary:[Display omitted] •DIBAL-H promotes the cyclization of o-(silylethynyl)benzyl ethers to 2-silylindenes.•Diethylaluminum chloride assists the DIBAL-H-promoted cyclization.•The DIBAL-H-promoted cyclization is applicable to the synthesis of benzo[b]siloles. The reaction of o-[2-(trimethylsilyl)ethynyl]benzyl methyl ethers with diisobutylaluminum hydride (DIBAL-H) gave 2-(trimethylsilyl)indenes in good yields. This cyclization proceeds by regio- and stereoselective hydroalumination of the alkyne moiety followed by intramolecular nucleophilic substitution. o-[2-(Trimethylsilyl)ethynyl]phenylsilyl methyl ethers also underwent the DIBAL-H promoted-cyclization to be converted into 2-(trimethylsilyl)benzosiloles in good yields. This approach provides straightforward and efficient way to construct benzosiloles from readily available organosilanes.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.06.123