Lewis acid-mediated carboxylation of aryl- and allylsilanes with carbon dioxide

Tetsutaro Hattori; Yutaka Suzuki; Sotaro Miyano

doi:10.1246/cl.2003.454

Lewis acid-mediated carboxylation of aryl- and allylsilanes with carbon dioxide

Tetsutaro Hattori, Yutaka Suzuki, Sotaro Miyano

ENG - Biomolecular Engineering

Tohoku University

Research output: Contribution to journal › Article › peer-review

23 Citations (Scopus)

Abstract

Aryl- and allylsilanes are carboxylated with CO₂ with the aid of aluminum-based Lewis acids, to give aromatic and β, γ-unsaturated carboxylic acids in fair to good yields, respectively. Formation of the former is rationalized by an aromatic electrophilic substitution by CO₂ activated by the Lewis acid, while the latter a nucleophilic addition of in situ-generated allylaluminum species to CO₂.

Original language	English
Pages (from-to)	454-455
Number of pages	2
Journal	Chemistry Letters
Volume	32
Issue number	5
DOIs	https://doi.org/10.1246/cl.2003.454
Publication status	Published - 2003 May 5

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abstract = "Aryl- and allylsilanes are carboxylated with CO2 with the aid of aluminum-based Lewis acids, to give aromatic and β, γ-unsaturated carboxylic acids in fair to good yields, respectively. Formation of the former is rationalized by an aromatic electrophilic substitution by CO2 activated by the Lewis acid, while the latter a nucleophilic addition of in situ-generated allylaluminum species to CO2.",

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AU - Miyano, Sotaro

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N2 - Aryl- and allylsilanes are carboxylated with CO2 with the aid of aluminum-based Lewis acids, to give aromatic and β, γ-unsaturated carboxylic acids in fair to good yields, respectively. Formation of the former is rationalized by an aromatic electrophilic substitution by CO2 activated by the Lewis acid, while the latter a nucleophilic addition of in situ-generated allylaluminum species to CO2.

AB - Aryl- and allylsilanes are carboxylated with CO2 with the aid of aluminum-based Lewis acids, to give aromatic and β, γ-unsaturated carboxylic acids in fair to good yields, respectively. Formation of the former is rationalized by an aromatic electrophilic substitution by CO2 activated by the Lewis acid, while the latter a nucleophilic addition of in situ-generated allylaluminum species to CO2.

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ER -

Lewis acid-mediated carboxylation of aryl- and allylsilanes with carbon dioxide

Abstract

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