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^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

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

17 Citations (Scopus)

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.

Original language	English
Pages (from-to)	981-987
Number of pages	7
Journal	Chinese Journal of Chemistry
Volume	28
Issue number	6
DOIs	https://doi.org/10.1002/cjoc.201090182
Publication status	Published - Jun 2010

Keywords

1,4-addition
CsF
Cyanides
Enones
Regioselectivity

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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 - Yang, Jingya

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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U2 - 10.1002/cjoc.201090182

DO - 10.1002/cjoc.201090182

M3 - Article

AN - SCOPUS:77954482390

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JO - Chinese Journal of Chemistry

JF - Chinese Journal of Chemistry

IS - 6

ER -

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

Abstract

Keywords

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