Chinese Journal of Organic Chemistry >
One-Step C- or O-Benzylation of 1,3-Dicarbonyls with Benzyl Alcohols Promoted by Perfluoroalkanosulfonyl Fluoride
Received date: 2016-08-11
Revised date: 2016-09-07
Online 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(RfSO2F) 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 RfSO2F 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(RfSO2F):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 RfSO2F in organic synthesis was further broadened.
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
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