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Platinum-Catalyzed Reactions of 2,3-Bis(diisopropylsilyl)thiophene with Alkynes.

ABSTRACT: The reactions of 2,3-bis(diisopropylsilyl)thiophene (1) with diphenylacetylene, phenylacetylene, trimethylsilylacetylene, and mesitylacetylene have been reported. The reactions of 1 with diphenylacetylene and phenylacetylene in the presence of a catalytic amount of tetrakis(triphenylphosphine)platinum(0) at 80 °C gave [1,4]disilino[2,3-b]thiophene derivatives. With trimethylsilylacetylene, 1 afforded two types of products arising from sp-hybridized C-H bond activation of the acetylene, together with [1,3]disilolo[4,5-b]thiophene derivatives. A similar treatment of 1 with mesitylacetylene produced two regioisomers of products arising from the C-H bond activation of mesitylacetylene. Theoretical calculations for the intramolecular reactions of 10a and 10b are also discussed.

SUBMITTER: Naka A

PROVIDER: S-EPMC6645491 | biostudies-literature | 2017 Nov

REPOSITORIES: biostudies-literature

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Platinum-Catalyzed Reactions of 2,3-Bis(diisopropylsilyl)thiophene with Alkynes.

Naka Akinobu A Mihara Takashi T Kobayashi Hisayoshi H Ishikawa Mitsuo M

ACS omega 20171130 11

The reactions of 2,3-bis(diisopropylsilyl)thiophene (1) with diphenylacetylene, phenylacetylene, trimethylsilylacetylene, and mesitylacetylene have been reported. The reactions of 1 with diphenylacetylene and phenylacetylene in the presence of a catalytic amount of tetrakis(triphenylphosphine)platinum(0) at 80 °C gave [1,4]disilino[2,3-b]thiophene derivatives. With trimethylsilylacetylene, 1 afforded two types of products arising from sp-hybridized C-H bond activation ...[more]

PMID: 31457388

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