Copper-catalyzed Cross-coupling Reaction between Aryl(trialkyl)silanes and Alkyl Halides

Komiyama, Takeshi; Minami, Yasunori; Hiyama, Tamejiro

doi:10.1246/cl.180426

Cited by 4 publications

(1 citation statement)

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“…In this alkylation reaction, the CuI catalyst in combination with the 1,10‐phenanthroline ligand was effective. For example, 2‐triethylsilylbenzo[ b ]thiophene was treated with hexyl iodide to form the 2‐hexylated product in good yield (Scheme ) . In a manner similar to the previous cases, trimethylsilyl, tert ‐butyldimethylsilyl, and bulky triisopropylsilyl groups were tolerated under the reaction conditions, and the alkylated products were obtained in good yields.…”

Section: Copper(i)‐catalyzed Alkylationmentioning

confidence: 99%

Designing Cross‐Coupling Reactions using Aryl(trialkyl)silanes

Minami

Hiyama

2018

Chemistry A European J

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Organo(trialkyl)silanes have several advantages, including high stability, low toxicity, good solubility, easy handling, and ready availability compared with heteroatom-substituted silanes. However, methods for the cross-coupling of organo(trialkyl)silanes are limited, most probably because of their exceeding robustness. Thus, a practical method for the cross-coupling of organo(trialkyl)silanes has been a long-standing challenging research target. This article discusses how aryl(trialkyl)silanes can be used in cross-coupling reactions. A pioneering example is Cu catalytic conditions with the use of electron-accepting aryl- or heteroaryl(triethyl)silanes and aryl iodides. The reaction forms biaryls or teraryls. This design concept can be extended to Pd/Cu -catalyzed cross-coupling polymerization reactions between such silanes and aryl bromides or chlorides and to Cu -catalyzed alkylation using alkyl halides.

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Section: Copper(i)‐catalyzed Alkylationmentioning

confidence: 99%