Highly efficient syntheses of β-cyanoketones via conjugate addition of Me3SiCN to aromatic enones

Jingya Yang; Fuxue Chen

doi:10.1002/cjoc.201090182

Highly efficient syntheses of β-cyanoketones via conjugate addition of Me₃SiCN to aromatic enones

Jingya Yang, Fuxue Chen^*

^*此作品的通讯作者

化学与化工学院

科研成果: 期刊稿件 › 文章 › 同行评审

17 引用（Scopus）

摘要

An efficient 1,4-addition of Me₃SiCN to aromatic enones has been achieved with excellent yields (91%-99%) using CsF (1 mol%) as the catalyst and H₂O (4 equiv.) as the additive in refluxing dioxane within 7 h. The perfect regioselectivity is proposed accounting from H₂O-facilitated reversion of the 1,2-adduct in the presence of CsF and subsequent irreversible 1,4-addition reaction.

源语言	英语
页（从-至）	981-987
页数	7
期刊	Chinese Journal of Chemistry
卷	28
期	6
DOI	https://doi.org/10.1002/cjoc.201090182
出版状态	已出版 - 6月 2010

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abstract = "An efficient 1,4-addition of Me3SiCN to aromatic enones has been achieved with excellent yields (91%-99%) using CsF (1 mol%) as the catalyst and H2O (4 equiv.) as the additive in refluxing dioxane within 7 h. The perfect regioselectivity is proposed accounting from H2O-facilitated reversion of the 1,2-adduct in the presence of CsF and subsequent irreversible 1,4-addition reaction.",

keywords = "1,4-addition, CsF, Cyanides, Enones, Regioselectivity",

author = "Jingya Yang and Fuxue Chen",

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AU - Chen, Fuxue

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N2 - An efficient 1,4-addition of Me3SiCN to aromatic enones has been achieved with excellent yields (91%-99%) using CsF (1 mol%) as the catalyst and H2O (4 equiv.) as the additive in refluxing dioxane within 7 h. The perfect regioselectivity is proposed accounting from H2O-facilitated reversion of the 1,2-adduct in the presence of CsF and subsequent irreversible 1,4-addition reaction.

AB - An efficient 1,4-addition of Me3SiCN to aromatic enones has been achieved with excellent yields (91%-99%) using CsF (1 mol%) as the catalyst and H2O (4 equiv.) as the additive in refluxing dioxane within 7 h. The perfect regioselectivity is proposed accounting from H2O-facilitated reversion of the 1,2-adduct in the presence of CsF and subsequent irreversible 1,4-addition reaction.

KW - 1,4-addition

KW - CsF

KW - Cyanides

KW - Enones

KW - Regioselectivity

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JF - Chinese Journal of Chemistry

IS - 6

ER -

Highly efficient syntheses of β-cyanoketones via conjugate addition of Me3SiCN to aromatic enones

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Highly efficient syntheses of β-cyanoketones via conjugate addition of Me₃SiCN to aromatic enones