Chinese Journal of Organic Chemistry >
One-Step Enol Esterification of 1,3-Dicarbonyls with Carboxylic Acids Activated by Perfluoroalkanosulfonyl Fluoride
Received date: 2019-01-10
Revised date: 2019-03-24
Online published: 2019-04-09
Supported by
Project supported by the National Natural Science Foundation of China (No. 21362022).
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 (RfSO2F) 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 RfSO2F 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(RfSO2F):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 RfSO2F in organic synthesis was further expanded.
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]. Chinese Journal of Organic Chemistry, 2019 , 39(7) : 2042 -2047 . DOI: 10.6023/cjoc201901012
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