One-Step C- or O-Benzylation of 1,3-Dicarbonyls with Benzyl Alcohols Promoted by Perfluoroalkanosulfonyl Fluoride

doi:10.6023/cjoc201608008

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (1): 196-202.DOI: 10.6023/cjoc201608008 Previous Articles Next Articles

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全氟烷基磺酰氟应用于1,3-二羰基化合物和苄醇衍生物之间一步C-或O-苄基化反应

严兆华^a, 金红爱^a, 余信权^a, 王汪阳^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:2016-08-11 修回日期:2016-09-07 发布日期:2016-09-12
通讯作者: 严兆华, 田伟生 E-mail:yanzh@ncu.edu.cn
基金资助:
国家自然科学基金（No. 21362022）资助项目.

One-Step C- or O-Benzylation of 1,3-Dicarbonyls with Benzyl Alcohols Promoted by Perfluoroalkanosulfonyl Fluoride

Yan Zhaohua^a, Jin Hongai^a, Yu Xinquan^a, Wang Wangyang^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:2016-08-11 Revised:2016-09-07 Published:2016-09-12
Supported by:
Project supported by the National Natural Science Foundation of China(No. 21362022).

C- or O-benzylation of 1,3-dicarbonyl compounds is one of the most fundamental methodologies for carbon-carbon or carbon-oxygen bond formation in organic synthesis.Perfluoroalkanosulfonyl fluoride(R_fSO₂F) is a class of excellent hy-droxyl-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 C- or O-benzylation of 1,3-dicarbonyl compounds(1,3-diketones and β-ketonic esters) with benzyl alcohols promoted by R_fSO₂F in alkaline media was explored,and the corresponding C- or O-benzylation products were generated in medium to excellent yields.The optimized reaction conditions:1,8-diazabicyclo[5.4.0]undec-7-ene(DBU) as base,CH₂Cl₂ as solvent,n-C₄F₉SO₂F,room temperature and the molar ratio of n(1,3-dicarbonyls):n(benzyl alco-hols):n(R_fSO₂F):n(DBU) is 1.0:1.0:1.0:2.2.A novel reagent system for the direct C- or O-benzylation of 1,3-dicarbonyl compounds with benzyl alcohols was developed.The application scope of R_fSO₂F in organic synthesis was further broadened.

Key words: perfluoroalkanosulfonyl fluoride, 1,3-dicarbonyl compounds, benzyl alcohols, benzylation

Cite this article

Yan Zhaohua, Jin Hongai, Yu Xinquan, Wang Wangyang, Tian Weisheng. One-Step C- or O-Benzylation of 1,3-Dicarbonyls with Benzyl Alcohols Promoted by Perfluoroalkanosulfonyl Fluoride[J]. Chin. J. Org. Chem., 2017, 37(1): 196-202.

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全氟烷基磺酰氟应用于1,3-二羰基化合物和苄醇衍生物之间一步C-或O-苄基化反应

One-Step C- or O-Benzylation of 1,3-Dicarbonyls with Benzyl Alcohols Promoted by Perfluoroalkanosulfonyl Fluoride

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