Citation: 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]. Chinese Journal of Organic Chemistry, ;2017, 37(1): 196-202. doi: 10.6023/cjoc201608008 shu

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

Corresponding author: Yan Zhaohua, yanzh@ncu.edu.cn Tian Weisheng,
Received Date: 11 August 2016
Revised Date: 7 September 2016

Fund Project: the National Natural Science Foundation of China 21362022

Figures(1)

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.
- perfluoroalkanosulfonyl fluoride,
- 1, 3-dicarbonyl compounds,
- benzyl alcohols,
- benzylation
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