Health & Environmental Research Online (HERO)


Print Feedback Export to File
8382756 
Journal Article 
One-step C- or O-benzylation of 1,3-dicarbonyls with benzyl alcohols promoted by perfluoroalkanosulfonyl fluoride 
Yan, Z; Jin, H; Yu, X; Wang, W; Tian, W 
2017 
1 
Youji Huaxue / Chinese Journal of Organic Chemistry
ISSN: 0253-2786 
Science Press 
37 
1 
196-202 
Chinese 
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 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 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 alcohols):n(RfSO2F):n(DBU) is 1.0:1.0:1.0:2.2. A novel reagent system for the direct Cor O-benzylation of 1,3-dicarbonyl compounds with benzyl alcohols was developed. The application scope of RfSO2F in organic synthesis was further broadened. © 2017 Chinese Chemical Society & SIOC, CAS. 
1,3-dicarbonyl compounds; Benzyl alcohols; Benzylation; Perfluoroalkanosulfonyl fluoride