One-Step Enol Esterification of 1,3-Dicarbonyls with Carboxylic Acids Activated by Perfluoroalkanosulfonyl Fluoride

doi:10.6023/cjoc201901012

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (7): 2042-2047.DOI: 10.6023/cjoc201901012 Previous Articles Next Articles

Notes

全氟烷基磺酰氟活化羧酸和1,3-二羰基化合物之间一步O-酰基化反应

严兆华^a, 王彦梅^a, 金红爱^a, 艾城美^a, 田伟生^b

a 南昌大学化学学院南昌 330031;
b 中国科学院上海有机化学研究所上海 200032

收稿日期:2019-01-10 修回日期:2019-03-24 发布日期:2019-04-09
通讯作者: 严兆华, 田伟生 E-mail:yanzh@ncu.edu.cn;wstian@sioc.ac.cn
基金资助:
国家自然科学基金（No.21362022）资助项目.

One-Step Enol Esterification of 1,3-Dicarbonyls with Carboxylic Acids Activated by Perfluoroalkanosulfonyl Fluoride

Yan Zhaohua^a, Wang Yanmei^a, Jin Hong'ai^a, Ai Chengmei^a, Tian Weisheng^b

a College of Chemistry, Nanchang University, Nanchang 330031;
b Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2019-01-10 Revised:2019-03-24 Published:2019-04-09
Contact: 10.6023/cjoc201901012 E-mail:yanzh@ncu.edu.cn;wstian@sioc.ac.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21362022).

1. One-Step Enol Esterification of 1,3-Dicarbonyls with Carboxylic Acids Activated by Perfluoroalkanosulfonyl Fluoride.PDF(3470KB)

Abstract

O-Acylation of 1,3-dicarbonyl compounds provides enol esters which act as precursors for the synthesis of chiral alcohols, natural products, heterocycles and functional materials. Perfluoroalkanosulfonyl fluoride (R_fSO₂F) is a class of excellent hydroxyl-activating reagent, and has been extensively developed and used in the formation of C-F, C-O, C-N and C-S bonds in organic synthesis. In this work one-step O-acylation of 1,3-dicarbonyl compounds (1,3-diketones and β-ketonic esters) with carboxylic acids activated by R_fSO₂F in alkaline media was disclosed, and the corresponding O-acylation products (enol esters) were generated in moderate to good yields. The optimized reaction conditions are as follows:1,8-diazabicyclo-[5.4.0]undec-7-ene (DBU) as base, CH₂Cl₂ as solvent, n-C₄F₉SO₂F as activating reagent, room temperature for 30 min and the molar ratio of n(1,3-dicarbonyls):n(RCOOH):n(R_fSO₂F):n(DBU) being 1.0:1.0:1.0:4.0. A novel reagent for one-step O-acylation of 1,3-dicarbonyl compounds with carboxylic acids was developed. The application of R_fSO₂F in organic synthesis was further expanded.

Key words: perfluoroalkanosulfonyl fluoride, 1,3-dicarbonyl compound, carboxylic acids, enol ester

Cite this article

Yan Zhaohua, Wang Yanmei, Jin Hong'ai, Ai Chengmei, Tian Weisheng. One-Step Enol Esterification of 1,3-Dicarbonyls with Carboxylic Acids Activated by Perfluoroalkanosulfonyl Fluoride[J]. Chin. J. Org. Chem., 2019, 39(7): 2042-2047.

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全氟烷基磺酰氟活化羧酸和1,3-二羰基化合物之间一步O-酰基化反应

One-Step Enol Esterification of 1,3-Dicarbonyls with Carboxylic Acids Activated by Perfluoroalkanosulfonyl Fluoride

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