Selective Introduction of Trifluoroacetyl Group to β‐ and δ‐Position of Aromatic Conjugated Esters: Facile Synthesis of Fluorine‐containing Keto Esters,Asian Journal of Organic Chemistry

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Selective Introduction of Trifluoroacetyl Group to β‐ and δ‐Position of Aromatic Conjugated Esters: Facile Synthesis of Fluorine‐containing Keto Esters
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2019-01-28 , DOI: 10.1002/ajoc.201800741
Tianyuan Zhang ₁ , Yuhei Shimizu ₁ , Kazuyuki Shimizu ₁ , Mitsuhiro Abe ₁ , Suhua Zheng ₁ , Hirofumi Maekawa ₁

Affiliation

An approach to trifluoroacetylation of aromatic conjugated esters successfully led to the efficient and selective introduction of trifluoroacetyl group to the electron‐deficient β‐ or δ‐carbon atom of ester under mild reaction conditions by magnesium‐promoted reduction, followed by deacetalization with trifluoroacetic acid in moderate to good yields. A variety of fluorinated keto esters derived from ethyl cinnamates and β, γ‐ or γ‐, δ‐unsaturated fluorinated keto esters from aromatic dienoesters with a longer conjugation system were synthesized through this simple methodology utilizing ethyl trifluoroacetate as a fluorine‐containing carbon source.

中文翻译：

将三氟乙酰基选择性引入芳族共轭酯的β和δ位置：含氟酮酯的简便合成

芳香族共轭酯的三氟乙酰化方法成功地导致了镁的促进还原，在温和的反应条件下，将三氟乙酰基有效且选择性地引入了酯的电子不足的β-或δ-碳原子，然后在三氟乙酸中进行了脱缩醛化反应。中等至良好的产量。通过这种简单的方法，利用三氟乙酸乙酯作为氟碳源，从肉桂酸乙酯和芳香族二烯酸酯的β，γ-或γ-，δ-，δ-不饱和氟化酮酯衍生出了多种氟化酮酯。

更新日期：2019-01-28

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