Completely selective synthesis of (E)-β-(triethylsilyl) styrenes by Fe3(CO)12-catalyzed reaction of styrenes with triethylsilane

Fumitoshi Kakiuchi, Yasuo Tanaka, Naoto Chatani, Shinji Murai

Research output: Contribution to journalArticle

70 Citations (Scopus)

Abstract

Using Fe3(CO)12 as the catalyst, the reaction of styrenes (C6H5CHCH2, p-CH3C6H4CHCH2, p- ClC6H4CHCH2, and p-CH3OC6H4CHCH2) with triethyisilane gave (E)-β-(triethylsilyl)styrenes (2a, (E)-C6H5CHCHSiEt3; 2b, (E)-p-CH3C6H4CHCHSiEt3; 2c, (E)-p-ClC 6H4CHCHSiEt3; 2d, (E)-p-CH3OC6H4CHCHSiEt3) in 66-89% yields with complete selectivity. Similarly, Fe2(CO)9 also catalyzed dehydrogenative silylation again, with complete selectivity but in low yields. The reaction of styrene with treithylsilane, catalysed by OS3(CO)12, gave a mixture of the corresponding vinylsilane (dehydrogenative silylation product) and alkylsilane (hydrosilylation product).

Original languageEnglish
Pages (from-to)45-47
Number of pages3
JournalJournal of Organometallic Chemistry
Volume456
Issue number1
DOIs
Publication statusPublished - 1993 Aug 24
Externally publishedYes

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Styrenes
styrenes
Styrene
synthesis
selectivity
Catalysts
catalysts
products
triethylsilane

ASJC Scopus subject areas

  • Biochemistry
  • Chemical Engineering (miscellaneous)
  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Science (miscellaneous)
  • Materials Chemistry

Cite this

Completely selective synthesis of (E)-β-(triethylsilyl) styrenes by Fe3(CO)12-catalyzed reaction of styrenes with triethylsilane. / Kakiuchi, Fumitoshi; Tanaka, Yasuo; Chatani, Naoto; Murai, Shinji.

In: Journal of Organometallic Chemistry, Vol. 456, No. 1, 24.08.1993, p. 45-47.

Research output: Contribution to journalArticle

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title = "Completely selective synthesis of (E)-β-(triethylsilyl) styrenes by Fe3(CO)12-catalyzed reaction of styrenes with triethylsilane",
abstract = "Using Fe3(CO)12 as the catalyst, the reaction of styrenes (C6H5CHCH2, p-CH3C6H4CHCH2, p- ClC6H4CHCH2, and p-CH3OC6H4CHCH2) with triethyisilane gave (E)-β-(triethylsilyl)styrenes (2a, (E)-C6H5CHCHSiEt3; 2b, (E)-p-CH3C6H4CHCHSiEt3; 2c, (E)-p-ClC 6H4CHCHSiEt3; 2d, (E)-p-CH3OC6H4CHCHSiEt3) in 66-89{\%} yields with complete selectivity. Similarly, Fe2(CO)9 also catalyzed dehydrogenative silylation again, with complete selectivity but in low yields. The reaction of styrene with treithylsilane, catalysed by OS3(CO)12, gave a mixture of the corresponding vinylsilane (dehydrogenative silylation product) and alkylsilane (hydrosilylation product).",
author = "Fumitoshi Kakiuchi and Yasuo Tanaka and Naoto Chatani and Shinji Murai",
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T1 - Completely selective synthesis of (E)-β-(triethylsilyl) styrenes by Fe3(CO)12-catalyzed reaction of styrenes with triethylsilane

AU - Kakiuchi, Fumitoshi

AU - Tanaka, Yasuo

AU - Chatani, Naoto

AU - Murai, Shinji

PY - 1993/8/24

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N2 - Using Fe3(CO)12 as the catalyst, the reaction of styrenes (C6H5CHCH2, p-CH3C6H4CHCH2, p- ClC6H4CHCH2, and p-CH3OC6H4CHCH2) with triethyisilane gave (E)-β-(triethylsilyl)styrenes (2a, (E)-C6H5CHCHSiEt3; 2b, (E)-p-CH3C6H4CHCHSiEt3; 2c, (E)-p-ClC 6H4CHCHSiEt3; 2d, (E)-p-CH3OC6H4CHCHSiEt3) in 66-89% yields with complete selectivity. Similarly, Fe2(CO)9 also catalyzed dehydrogenative silylation again, with complete selectivity but in low yields. The reaction of styrene with treithylsilane, catalysed by OS3(CO)12, gave a mixture of the corresponding vinylsilane (dehydrogenative silylation product) and alkylsilane (hydrosilylation product).

AB - Using Fe3(CO)12 as the catalyst, the reaction of styrenes (C6H5CHCH2, p-CH3C6H4CHCH2, p- ClC6H4CHCH2, and p-CH3OC6H4CHCH2) with triethyisilane gave (E)-β-(triethylsilyl)styrenes (2a, (E)-C6H5CHCHSiEt3; 2b, (E)-p-CH3C6H4CHCHSiEt3; 2c, (E)-p-ClC 6H4CHCHSiEt3; 2d, (E)-p-CH3OC6H4CHCHSiEt3) in 66-89% yields with complete selectivity. Similarly, Fe2(CO)9 also catalyzed dehydrogenative silylation again, with complete selectivity but in low yields. The reaction of styrene with treithylsilane, catalysed by OS3(CO)12, gave a mixture of the corresponding vinylsilane (dehydrogenative silylation product) and alkylsilane (hydrosilylation product).

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